NPASS Compound

Structure

CID255641 OpenBabel06191716062D 22 24 0 0 0 0 0 0 0 0999 V2000 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 -0.0000 2.0000 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 2.5981 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 2.5981 1.5000 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 1.7321 0.0000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 7 1 0 0 0 0 4 10 2 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 14 20 2 0 0 0 0 15 21 2 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.06
Volume:	291.273
LogP:	3.901
LogD:	2.451
LogS:	-4.037
# Rotatable Bonds:	2
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	2.846
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.192
MDCK Permeability:	5.660344868374523e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.494
20% Bioavailability (F20%):	0.072
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	96.58452606201172%
Volume Distribution (VD):	0.498
Pgp-substrate:	8.569942474365234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.931
CYP1A2-substrate:	0.605
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.533
CYP2C9-substrate:	0.708
CYP2D6-inhibitor:	0.323
CYP2D6-substrate:	0.195
CYP3A4-inhibitor:	0.148
CYP3A4-substrate:	0.057

ADMET: Excretion

Clearance (CL):	4.755
Half-life (T1/2):	0.682

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.013
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.641
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.569
Skin Sensitization:	0.928
Carcinogencity:	0.099
Eye Corrosion:	0.018
Eye Irritation:	0.937
Respiratory Toxicity:	0.754

Download Data

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

Natural Product: NPC255641

Natural Product ID:	NPC255641
*Common Name:**	Juzunol
IUPAC Name:	3,5-dihydroxy-2-(hydroxymethyl)-1-methoxyanthracene-9,10-dione
Synonyms:	Juzunol
Standard InCHIKey:	IUOYPUBCUGWNGT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O6/c1-22-16-9(6-17)11(19)5-8-13(16)14(20)7-3-2-4-10(18)12(7)15(8)21/h2-5,17-19H,6H2,1H3
SMILES:	COc1c(CO)c(cc2c1C(=O)c1cccc(c1C2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485657
PubChem CID:	12304766
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO13324	Euphorbia ingens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11734	Chara corallina	Species	Characeae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15917	Monilinia fructigena	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26859	Solanum curtipes	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13324	Euphorbia ingens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2868	Perna viridis	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO861	Siphonaria funiculata	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13446	Stachys recta	Species	Lamiaceae	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
Others	8

Activity Type	# Activity
Cell Line	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[496564]
NPT2	Others	Unspecified		Inhibition	=	100.0	%	PMID[496564]
NPT2	Others	Unspecified		Inhibition	=	51.1	%	PMID[496564]

☑ 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 NPC255641 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	390
0.1-0.2	1690
0.2-0.3	3790
0.3-0.4	9511
0.4-0.5	8838
0.5-0.6	3459
0.6-0.7	5544
0.7-0.8	5661
0.8-0.85	2562
0.85-0.9	1079
0.9-0.95	145
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC290954
0.9861	High Similarity	NPC147735
0.9793	High Similarity	NPC470569
0.979	High Similarity	NPC190648
0.979	High Similarity	NPC118027
0.979	High Similarity	NPC56433
0.979	High Similarity	NPC312929
0.979	High Similarity	NPC126767
0.979	High Similarity	NPC289042
0.979	High Similarity	NPC245584
0.9724	High Similarity	NPC470568
0.966	High Similarity	NPC208806
0.9592	High Similarity	NPC40356
0.9592	High Similarity	NPC154683
0.9589	High Similarity	NPC294646
0.958	High Similarity	NPC21599
0.958	High Similarity	NPC19896
0.958	High Similarity	NPC193703
0.9533	High Similarity	NPC324736
0.9514	High Similarity	NPC49282
0.9463	High Similarity	NPC66508
0.9463	High Similarity	NPC226656
0.9444	High Similarity	NPC48762
0.9396	High Similarity	NPC107109
0.9388	High Similarity	NPC329933
0.9384	High Similarity	NPC34802
0.9379	High Similarity	NPC34482
0.9379	High Similarity	NPC478019
0.9375	High Similarity	NPC167663
0.9338	High Similarity	NPC178976
0.9324	High Similarity	NPC202595
0.9315	High Similarity	NPC300540
0.9315	High Similarity	NPC470570
0.931	High Similarity	NPC475201
0.9306	High Similarity	NPC182255
0.9306	High Similarity	NPC49108
0.9306	High Similarity	NPC94076
0.9272	High Similarity	NPC77807
0.9272	High Similarity	NPC5379
0.9272	High Similarity	NPC14561
0.9267	High Similarity	NPC214632
0.9262	High Similarity	NPC474417
0.9262	High Similarity	NPC149526
0.9262	High Similarity	NPC230848
0.9262	High Similarity	NPC478148
0.9257	High Similarity	NPC80370
0.9241	High Similarity	NPC84266
0.9236	High Similarity	NPC101366
0.9236	High Similarity	NPC305845
0.9236	High Similarity	NPC204045
0.9231	High Similarity	NPC1268
0.9211	High Similarity	NPC199463
0.9211	High Similarity	NPC37543
0.9189	High Similarity	NPC2569
0.9189	High Similarity	NPC472056
0.9189	High Similarity	NPC172329
0.9189	High Similarity	NPC256672
0.9189	High Similarity	NPC27221
0.9189	High Similarity	NPC7025
0.9184	High Similarity	NPC225173
0.9184	High Similarity	NPC163846
0.9172	High Similarity	NPC268204
0.9172	High Similarity	NPC52789
0.9172	High Similarity	NPC135524
0.9172	High Similarity	NPC55832
0.9172	High Similarity	NPC26051
0.9167	High Similarity	NPC295384
0.9167	High Similarity	NPC472366
0.9156	High Similarity	NPC311740
0.9139	High Similarity	NPC329844
0.9139	High Similarity	NPC169990
0.9139	High Similarity	NPC93552
0.9139	High Similarity	NPC210942
0.9139	High Similarity	NPC135522
0.9133	High Similarity	NPC258249
0.9133	High Similarity	NPC46882
0.9133	High Similarity	NPC232645
0.9133	High Similarity	NPC132990
0.9133	High Similarity	NPC72958
0.9128	High Similarity	NPC158338
0.9128	High Similarity	NPC100985
0.9128	High Similarity	NPC97028
0.9128	High Similarity	NPC65775
0.9128	High Similarity	NPC10027
0.9128	High Similarity	NPC97029
0.9128	High Similarity	NPC65589
0.9128	High Similarity	NPC288036
0.9122	High Similarity	NPC125801
0.9122	High Similarity	NPC7943
0.9122	High Similarity	NPC71055
0.9122	High Similarity	NPC22005
0.9122	High Similarity	NPC123202
0.9116	High Similarity	NPC28632
0.9116	High Similarity	NPC476055
0.9103	High Similarity	NPC219917
0.9103	High Similarity	NPC172250
0.9103	High Similarity	NPC253822
0.9103	High Similarity	NPC215311
0.9103	High Similarity	NPC80962
0.9103	High Similarity	NPC326109
0.9103	High Similarity	NPC48624
0.9103	High Similarity	NPC144118
0.9103	High Similarity	NPC204985
0.9103	High Similarity	NPC213659
0.9103	High Similarity	NPC259166
0.9097	High Similarity	NPC12175
0.9097	High Similarity	NPC309154
0.9097	High Similarity	NPC55162
0.9097	High Similarity	NPC90665
0.9097	High Similarity	NPC138099
0.9097	High Similarity	NPC279668
0.9097	High Similarity	NPC278323
0.9097	High Similarity	NPC190457
0.9097	High Similarity	NPC242994
0.9091	High Similarity	NPC284495
0.9091	High Similarity	NPC472060
0.9091	High Similarity	NPC471905
0.9091	High Similarity	NPC470342
0.9091	High Similarity	NPC53414
0.9091	High Similarity	NPC53206
0.9091	High Similarity	NPC84571
0.9091	High Similarity	NPC472052
0.9085	High Similarity	NPC263483
0.9073	High Similarity	NPC470337
0.9073	High Similarity	NPC149889
0.9073	High Similarity	NPC180944
0.9073	High Similarity	NPC470338
0.9073	High Similarity	NPC312338
0.9073	High Similarity	NPC470340
0.9073	High Similarity	NPC51824
0.9073	High Similarity	NPC87708
0.9073	High Similarity	NPC113608
0.9073	High Similarity	NPC268992
0.9048	High Similarity	NPC475705
0.9048	High Similarity	NPC471906
0.9048	High Similarity	NPC244691
0.9048	High Similarity	NPC117836
0.9048	High Similarity	NPC51887
0.9048	High Similarity	NPC476178
0.9041	High Similarity	NPC469404
0.9041	High Similarity	NPC40118
0.9041	High Similarity	NPC470087
0.9041	High Similarity	NPC321980
0.9041	High Similarity	NPC126534
0.9041	High Similarity	NPC232021
0.9038	High Similarity	NPC101769
0.9034	High Similarity	NPC169452
0.9034	High Similarity	NPC477956
0.9034	High Similarity	NPC470211
0.9034	High Similarity	NPC283429
0.9034	High Similarity	NPC109232
0.9034	High Similarity	NPC181560
0.9028	High Similarity	NPC472419
0.9028	High Similarity	NPC7013
0.9028	High Similarity	NPC162680
0.9028	High Similarity	NPC303644
0.9028	High Similarity	NPC181124
0.9028	High Similarity	NPC116632
0.9028	High Similarity	NPC212767
0.9028	High Similarity	NPC209560
0.9028	High Similarity	NPC294409
0.9021	High Similarity	NPC141934
0.9021	High Similarity	NPC254847
0.9013	High Similarity	NPC155686
0.9007	High Similarity	NPC39819
0.9007	High Similarity	NPC473201
0.9007	High Similarity	NPC302783
0.9007	High Similarity	NPC118427
0.8987	High Similarity	NPC234497
0.8987	High Similarity	NPC470341
0.8987	High Similarity	NPC324522
0.8987	High Similarity	NPC472058
0.8987	High Similarity	NPC105414
0.8986	High Similarity	NPC469764
0.898	High Similarity	NPC3732
0.898	High Similarity	NPC310340
0.898	High Similarity	NPC297600
0.8973	High Similarity	NPC124365
0.8973	High Similarity	NPC265178
0.8973	High Similarity	NPC11056
0.8968	High Similarity	NPC470810
0.8966	High Similarity	NPC472368
0.8966	High Similarity	NPC243528
0.8966	High Similarity	NPC251681
0.8966	High Similarity	NPC21350
0.8961	High Similarity	NPC201127
0.8961	High Similarity	NPC44199
0.8961	High Similarity	NPC212967
0.8961	High Similarity	NPC246647
0.8961	High Similarity	NPC96342
0.8961	High Similarity	NPC164110
0.8961	High Similarity	NPC474637
0.8958	High Similarity	NPC168105
0.8958	High Similarity	NPC477244
0.8958	High Similarity	NPC1486
0.8958	High Similarity	NPC98115
0.8958	High Similarity	NPC235428
0.8958	High Similarity	NPC66349
0.8958	High Similarity	NPC186838
0.8958	High Similarity	NPC477242

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 NPC255641 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	1015
0.2-0.3	1475
0.3-0.4	2625
0.4-0.5	1920
0.5-0.6	1115
0.6-0.7	420
0.7-0.8	170
0.8-0.85	36
0.85-0.9	14
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9021	High Similarity	NPD1509	Clinical (unspecified phase)
0.8889	High Similarity	NPD1510	Phase 2
0.8881	High Similarity	NPD1607	Approved
0.8854	High Similarity	NPD6232	Discontinued
0.8805	High Similarity	NPD7473	Discontinued
0.8766	High Similarity	NPD7819	Suspended
0.8741	High Similarity	NPD1240	Approved
0.8671	High Similarity	NPD6959	Discontinued
0.8609	High Similarity	NPD2533	Approved
0.8609	High Similarity	NPD2532	Approved
0.8609	High Similarity	NPD4378	Clinical (unspecified phase)
0.8609	High Similarity	NPD2534	Approved
0.8581	High Similarity	NPD1549	Phase 2
0.8571	High Similarity	NPD4380	Phase 2
0.8526	High Similarity	NPD2393	Clinical (unspecified phase)
0.8514	High Similarity	NPD1550	Clinical (unspecified phase)
0.8514	High Similarity	NPD1552	Clinical (unspecified phase)
0.8506	High Similarity	NPD3226	Approved
0.8487	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD7411	Suspended
0.8344	Intermediate Similarity	NPD1934	Approved
0.8322	Intermediate Similarity	NPD2796	Approved
0.8301	Intermediate Similarity	NPD7390	Discontinued
0.8252	Intermediate Similarity	NPD1470	Approved
0.825	Intermediate Similarity	NPD3749	Approved
0.825	Intermediate Similarity	NPD7075	Discontinued
0.8242	Intermediate Similarity	NPD5844	Phase 1
0.8224	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD3750	Approved
0.82	Intermediate Similarity	NPD2935	Discontinued
0.8187	Intermediate Similarity	NPD3882	Suspended
0.8187	Intermediate Similarity	NPD7768	Phase 2
0.8182	Intermediate Similarity	NPD1511	Approved
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD2801	Approved
0.8171	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD2346	Discontinued
0.8113	Intermediate Similarity	NPD6801	Discontinued
0.8101	Intermediate Similarity	NPD6599	Discontinued
0.8092	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1551	Phase 2
0.8077	Intermediate Similarity	NPD1512	Approved
0.8061	Intermediate Similarity	NPD6166	Phase 2
0.8061	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2800	Approved
0.8037	Intermediate Similarity	NPD5494	Approved
0.8025	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6559	Discontinued
0.7987	Intermediate Similarity	NPD943	Approved
0.7972	Intermediate Similarity	NPD1201	Approved
0.7964	Intermediate Similarity	NPD3818	Discontinued
0.7961	Intermediate Similarity	NPD5404	Approved
0.7961	Intermediate Similarity	NPD5405	Approved
0.7961	Intermediate Similarity	NPD5406	Approved
0.7961	Intermediate Similarity	NPD5408	Approved
0.7949	Intermediate Similarity	NPD6799	Approved
0.7939	Intermediate Similarity	NPD5710	Approved
0.7939	Intermediate Similarity	NPD5711	Approved
0.7908	Intermediate Similarity	NPD2344	Approved
0.7895	Intermediate Similarity	NPD3748	Approved
0.7881	Intermediate Similarity	NPD6651	Approved
0.7853	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6100	Approved
0.7843	Intermediate Similarity	NPD6099	Approved
0.7824	Intermediate Similarity	NPD5953	Discontinued
0.7812	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD920	Approved
0.7791	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD6776	Approved
0.7778	Intermediate Similarity	NPD6781	Approved
0.7778	Intermediate Similarity	NPD6779	Approved
0.7778	Intermediate Similarity	NPD6778	Approved
0.7778	Intermediate Similarity	NPD2799	Discontinued
0.7778	Intermediate Similarity	NPD6777	Approved
0.7778	Intermediate Similarity	NPD6782	Approved
0.7778	Intermediate Similarity	NPD6780	Approved
0.7765	Intermediate Similarity	NPD7074	Phase 3
0.7756	Intermediate Similarity	NPD7003	Approved
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7733	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2309	Approved
0.7706	Intermediate Similarity	NPD7054	Approved
0.7702	Intermediate Similarity	NPD7458	Discontinued
0.7692	Intermediate Similarity	NPD1243	Approved
0.7688	Intermediate Similarity	NPD8313	Approved
0.7688	Intermediate Similarity	NPD8312	Approved
0.7683	Intermediate Similarity	NPD5402	Approved
0.7673	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD37	Approved
0.7667	Intermediate Similarity	NPD4625	Phase 3
0.7662	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7472	Approved
0.7658	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7435	Discontinued
0.765	Intermediate Similarity	NPD7698	Approved
0.765	Intermediate Similarity	NPD7696	Phase 3
0.765	Intermediate Similarity	NPD7697	Approved
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7643	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD8151	Discontinued
0.7622	Intermediate Similarity	NPD1465	Phase 2
0.7616	Intermediate Similarity	NPD3764	Approved
0.7616	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.7616	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6797	Phase 2
0.7609	Intermediate Similarity	NPD7870	Phase 2
0.7609	Intermediate Similarity	NPD7871	Phase 2
0.7602	Intermediate Similarity	NPD7286	Phase 2
0.7584	Intermediate Similarity	NPD2798	Approved
0.7578	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5403	Approved
0.7574	Intermediate Similarity	NPD3926	Phase 2
0.7572	Intermediate Similarity	NPD7251	Discontinued
0.7568	Intermediate Similarity	NPD1283	Approved
0.7564	Intermediate Similarity	NPD1471	Phase 3
0.7562	Intermediate Similarity	NPD5401	Approved
0.7562	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD1247	Approved
0.7557	Intermediate Similarity	NPD8150	Discontinued
0.7551	Intermediate Similarity	NPD3972	Approved
0.7545	Intermediate Similarity	NPD919	Approved
0.753	Intermediate Similarity	NPD4967	Phase 2
0.753	Intermediate Similarity	NPD4965	Approved
0.753	Intermediate Similarity	NPD4966	Approved
0.7529	Intermediate Similarity	NPD7808	Phase 3
0.7529	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1651	Approved
0.7515	Intermediate Similarity	NPD7229	Phase 3
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD7701	Phase 2
0.7486	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4908	Phase 1
0.7468	Intermediate Similarity	NPD230	Phase 1
0.745	Intermediate Similarity	NPD1876	Approved
0.7442	Intermediate Similarity	NPD7177	Discontinued
0.744	Intermediate Similarity	NPD6234	Discontinued
0.7431	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6273	Approved
0.7407	Intermediate Similarity	NPD7874	Approved
0.7407	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6823	Phase 2
0.74	Intermediate Similarity	NPD1203	Approved
0.7377	Intermediate Similarity	NPD7700	Phase 2
0.7377	Intermediate Similarity	NPD7699	Phase 2
0.7368	Intermediate Similarity	NPD7801	Approved
0.7365	Intermediate Similarity	NPD1281	Approved
0.7365	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1610	Phase 2
0.7353	Intermediate Similarity	NPD7199	Phase 2
0.7351	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4626	Approved
0.7325	Intermediate Similarity	NPD4308	Phase 3
0.731	Intermediate Similarity	NPD3787	Discontinued
0.7308	Intermediate Similarity	NPD4360	Phase 2
0.7308	Intermediate Similarity	NPD4363	Phase 3
0.7305	Intermediate Similarity	NPD5761	Phase 2
0.7305	Intermediate Similarity	NPD5760	Phase 2
0.7285	Intermediate Similarity	NPD1164	Approved
0.7278	Intermediate Similarity	NPD4287	Approved
0.7273	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD411	Approved
0.7268	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4361	Phase 2
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7262	Intermediate Similarity	NPD4288	Approved
0.7255	Intermediate Similarity	NPD6832	Phase 2
0.7253	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6212	Phase 3
0.7253	Intermediate Similarity	NPD6213	Phase 3
0.725	Intermediate Similarity	NPD2654	Approved
0.7244	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7228	Approved
0.7241	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8320	Phase 1
0.7234	Intermediate Similarity	NPD8319	Approved
0.7233	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7033	Discontinued
0.7211	Intermediate Similarity	NPD9545	Approved
0.7211	Intermediate Similarity	NPD1548	Phase 1
0.7208	Intermediate Similarity	NPD3027	Phase 3
0.7207	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1608	Approved
0.72	Intermediate Similarity	NPD9717	Approved
0.7192	Intermediate Similarity	NPD9493	Approved
0.719	Intermediate Similarity	NPD9494	Approved
0.7188	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7783	Phase 2
0.7179	Intermediate Similarity	NPD2979	Phase 3
0.7179	Intermediate Similarity	NPD1612	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data