NPASS Compound

Structure

CID205766 OpenBabel06191715592D 29 32 0 0 0 0 0 0 0 0999 V2000 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 4.3301 1.5000 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 4.3301 0.5000 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 -0.0000 2.0000 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 2.5981 1.5000 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 1.5000 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 -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 2.5981 0.5000 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 0.8660 0.5000 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 1.7321 0.0000 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 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 1.7321 -1.0000 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 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 29 1 0 0 0 0 3 9 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 10 1 0 0 0 0 6 13 2 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 15 2 0 0 0 0 10 16 2 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 24 1 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 25 2 0 0 0 0 20 26 2 0 0 0 0 21 27 1 0 0 0 0 22 28 2 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.09
Volume:	387.373
LogP:	5.128
LogD:	2.714
LogS:	-6.343
# Rotatable Bonds:	3
TPSA:	121.13
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	2.732
Fsp3:	0.136
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.386
MDCK Permeability:	1.4508324966300279e-05
Pgp-inhibitor:	0.234
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.844
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	100.11368560791016%
Volume Distribution (VD):	0.368
Pgp-substrate:	1.4897122383117676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.926
CYP1A2-substrate:	0.309
CYP2C19-inhibitor:	0.2
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.721
CYP2C9-substrate:	0.35
CYP2D6-inhibitor:	0.192
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.314
CYP3A4-substrate:	0.081

ADMET: Excretion

Clearance (CL):	3.804
Half-life (T1/2):	0.077

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.812
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.604
Skin Sensitization:	0.625
Carcinogencity:	0.672
Eye Corrosion:	0.003
Eye Irritation:	0.94
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC205766

Natural Product ID:	NPC205766
*Common Name:**	Methyl 2-Ethyl-4,5,7-Trihydroxy-6,11-Dioxonaphthacenecarboxylate
IUPAC Name:	methyl 2-ethyl-4,5,7-trihydroxy-6,11-dioxotetracene-1-carboxylate
Synonyms:
Standard InCHIKey:	SNPUAXHAZYUTDJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H16O7/c1-3-9-7-14(24)17-11(15(9)22(28)29-2)8-12-18(21(17)27)20(26)16-10(19(12)25)5-4-6-13(16)23/h4-8,23-24,27H,3H2,1-2H3
SMILES:	CCc1cc(c2c(cc3c(C(=O)c4c(cccc4O)C3=O)c2O)c1C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL225917
PubChem CID:	16657205
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000022] Naphthacenes [CHEMONTID:0000155] Tetracenequinones

*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
NPO16872	Gypsophila paniculata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17469871]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31009220]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18467	Rosa henryi	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18467	Rosa henryi	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18467	Rosa henryi	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21777	Parmelia stygia	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22153	Nereis dumerilii	Species	Nereididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8816	Equisetum limosum	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21860	Viscum capitellatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16872	Gypsophila paniculata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21921	Valeriana alliariifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21968	Abutilon bidentatum	Species	Malvaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3585	Individual Protein	Integrin alpha-2	Homo sapiens	IC50	=	50000.0	nM	PMID[522902]

☑ 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 NPC205766 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	364
0.1-0.2	1674
0.2-0.3	3497
0.3-0.4	8465
0.4-0.5	10136
0.5-0.6	4120
0.6-0.7	6275
0.7-0.8	6531
0.8-0.85	1335
0.85-0.9	273
0.9-0.95	25
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC66029
0.9384	High Similarity	NPC119767
0.9333	High Similarity	NPC66508
0.9333	High Similarity	NPC226656
0.9315	High Similarity	NPC147250
0.9241	High Similarity	NPC66593
0.9178	High Similarity	NPC193703
0.9178	High Similarity	NPC21599
0.9167	High Similarity	NPC168471
0.915	High Similarity	NPC324736
0.9116	High Similarity	NPC34482
0.9103	High Similarity	NPC246638
0.9079	High Similarity	NPC318270
0.9054	High Similarity	NPC470570
0.9048	High Similarity	NPC48762
0.9045	High Similarity	NPC477835
0.9034	High Similarity	NPC315578
0.8993	High Similarity	NPC56433
0.8993	High Similarity	NPC118027
0.8993	High Similarity	NPC126767
0.8993	High Similarity	NPC289042
0.8993	High Similarity	NPC245584
0.8993	High Similarity	NPC190648
0.8993	High Similarity	NPC312929
0.8968	High Similarity	NPC472052
0.8968	High Similarity	NPC472060
0.8968	High Similarity	NPC470342
0.8966	High Similarity	NPC242994
0.8966	High Similarity	NPC138099
0.8966	High Similarity	NPC26924
0.8961	High Similarity	NPC317580
0.8958	High Similarity	NPC62272
0.894	High Similarity	NPC255641
0.894	High Similarity	NPC315520
0.894	High Similarity	NPC290954
0.894	High Similarity	NPC470568
0.8933	High Similarity	NPC172329
0.8933	High Similarity	NPC2569
0.8926	High Similarity	NPC163846
0.8926	High Similarity	NPC225173
0.8926	High Similarity	NPC314437
0.8912	High Similarity	NPC239136
0.8912	High Similarity	NPC19631
0.8912	High Similarity	NPC69755
0.8904	High Similarity	NPC181560
0.8904	High Similarity	NPC169452
0.8903	High Similarity	NPC326084
0.8897	High Similarity	NPC4214
0.8889	High Similarity	NPC182921
0.8889	High Similarity	NPC474824
0.8889	High Similarity	NPC470408
0.8889	High Similarity	NPC218870
0.8882	High Similarity	NPC470569
0.8874	High Similarity	NPC329933
0.8867	High Similarity	NPC125801
0.8867	High Similarity	NPC34802
0.8867	High Similarity	NPC37709
0.8851	High Similarity	NPC296752
0.8846	High Similarity	NPC475449
0.8839	High Similarity	NPC263483
0.8828	High Similarity	NPC53414
0.8828	High Similarity	NPC471905
0.8828	High Similarity	NPC53206
0.8824	High Similarity	NPC40356
0.8824	High Similarity	NPC154683
0.882	High Similarity	NPC477836
0.8819	High Similarity	NPC283088
0.8816	High Similarity	NPC477914
0.8816	High Similarity	NPC147735
0.8816	High Similarity	NPC294646
0.8811	High Similarity	NPC225051
0.88	High Similarity	NPC25844
0.8792	High Similarity	NPC151607
0.8792	High Similarity	NPC19896
0.8792	High Similarity	NPC42540
0.8784	High Similarity	NPC193555
0.8784	High Similarity	NPC135524
0.8774	High Similarity	NPC146211
0.8774	High Similarity	NPC474861
0.8767	High Similarity	NPC13715
0.8766	High Similarity	NPC208806
0.8766	High Similarity	NPC329844
0.8759	High Similarity	NPC118919
0.8759	High Similarity	NPC158481
0.8759	High Similarity	NPC254847
0.875	High Similarity	NPC76647
0.8742	High Similarity	NPC26386
0.8733	High Similarity	NPC49282
0.8733	High Similarity	NPC478019
0.8725	High Similarity	NPC159721
0.8725	High Similarity	NPC167663
0.8725	High Similarity	NPC313047
0.8725	High Similarity	NPC84266
0.8725	High Similarity	NPC474203
0.8725	High Similarity	NPC471682
0.8725	High Similarity	NPC295712
0.8725	High Similarity	NPC451542
0.8716	High Similarity	NPC204045
0.8716	High Similarity	NPC290550
0.8716	High Similarity	NPC305845
0.8707	High Similarity	NPC1268
0.8707	High Similarity	NPC19622
0.8707	High Similarity	NPC112789
0.8701	High Similarity	NPC175978
0.8699	High Similarity	NPC245923
0.8699	High Similarity	NPC194579
0.8693	High Similarity	NPC474660
0.8688	High Similarity	NPC30027
0.8684	High Similarity	NPC472841
0.8671	High Similarity	NPC72669
0.8671	High Similarity	NPC474517
0.8671	High Similarity	NPC472261
0.8667	High Similarity	NPC227841
0.8667	High Similarity	NPC10764
0.8658	High Similarity	NPC257644
0.8658	High Similarity	NPC250755
0.8658	High Similarity	NPC94076
0.8658	High Similarity	NPC49108
0.8658	High Similarity	NPC182255
0.8654	High Similarity	NPC313299
0.8654	High Similarity	NPC474360
0.8649	High Similarity	NPC275903
0.8645	High Similarity	NPC214632
0.8645	High Similarity	NPC474621
0.8645	High Similarity	NPC107109
0.8645	High Similarity	NPC474622
0.8645	High Similarity	NPC477691
0.8636	High Similarity	NPC149526
0.8636	High Similarity	NPC474417
0.8634	High Similarity	NPC470341
0.8634	High Similarity	NPC105414
0.8634	High Similarity	NPC324522
0.8634	High Similarity	NPC234497
0.8634	High Similarity	NPC472058
0.863	High Similarity	NPC191976
0.863	High Similarity	NPC155211
0.863	High Similarity	NPC474813
0.8627	High Similarity	NPC288036
0.8627	High Similarity	NPC233267
0.8627	High Similarity	NPC65589
0.8627	High Similarity	NPC97028
0.8627	High Similarity	NPC100985
0.8627	High Similarity	NPC158338
0.8627	High Similarity	NPC291049
0.8627	High Similarity	NPC97029
0.8627	High Similarity	NPC80370
0.8621	High Similarity	NPC50924
0.8621	High Similarity	NPC282780
0.8621	High Similarity	NPC44437
0.8621	High Similarity	NPC166480
0.8618	High Similarity	NPC52161
0.8618	High Similarity	NPC290194
0.8618	High Similarity	NPC162751
0.8609	High Similarity	NPC471683
0.8609	High Similarity	NPC12402
0.8608	High Similarity	NPC476506
0.8608	High Similarity	NPC284495
0.8608	High Similarity	NPC186325
0.86	High Similarity	NPC471731
0.86	High Similarity	NPC53016
0.86	High Similarity	NPC174905
0.86	High Similarity	NPC293545
0.86	High Similarity	NPC476473
0.8599	High Similarity	NPC178976
0.8599	High Similarity	NPC37543
0.8599	High Similarity	NPC164110
0.8599	High Similarity	NPC96342
0.8599	High Similarity	NPC199463
0.8599	High Similarity	NPC212967
0.8599	High Similarity	NPC246647
0.8599	High Similarity	NPC67197
0.8591	High Similarity	NPC472603
0.8581	High Similarity	NPC474534
0.8581	High Similarity	NPC217447
0.8581	High Similarity	NPC143438
0.8581	High Similarity	NPC474533
0.8581	High Similarity	NPC190457
0.8581	High Similarity	NPC477690
0.8581	High Similarity	NPC295339
0.8571	High Similarity	NPC280295
0.8571	High Similarity	NPC261292
0.8571	High Similarity	NPC470107
0.8571	High Similarity	NPC119929
0.8571	High Similarity	NPC301915
0.8571	High Similarity	NPC473466
0.8571	High Similarity	NPC53001
0.8571	High Similarity	NPC295036
0.8562	High Similarity	NPC7025
0.8562	High Similarity	NPC161632
0.8562	High Similarity	NPC105415
0.8562	High Similarity	NPC290695
0.8562	High Similarity	NPC152233
0.8562	High Similarity	NPC27221
0.8562	High Similarity	NPC106524
0.8562	High Similarity	NPC80035
0.8562	High Similarity	NPC221352
0.8562	High Similarity	NPC256672
0.8553	High Similarity	NPC110882
0.8553	High Similarity	NPC189552
0.8553	High Similarity	NPC300540

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 NPC205766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	981
0.2-0.3	1441
0.3-0.4	2595
0.4-0.5	2091
0.5-0.6	1134
0.6-0.7	370
0.7-0.8	171
0.8-0.85	23
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8958	High Similarity	NPD5404	Approved
0.8958	High Similarity	NPD5406	Approved
0.8958	High Similarity	NPD5405	Approved
0.8958	High Similarity	NPD5408	Approved
0.8854	High Similarity	NPD6232	Discontinued
0.8805	High Similarity	NPD7473	Discontinued
0.8759	High Similarity	NPD1509	Clinical (unspecified phase)
0.8667	High Similarity	NPD7390	Discontinued
0.8438	Intermediate Similarity	NPD6959	Discontinued
0.8408	Intermediate Similarity	NPD7819	Suspended
0.8387	Intermediate Similarity	NPD3226	Approved
0.8302	Intermediate Similarity	NPD7768	Phase 2
0.8282	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD7411	Suspended
0.8252	Intermediate Similarity	NPD1470	Approved
0.825	Intermediate Similarity	NPD3749	Approved
0.8247	Intermediate Similarity	NPD2532	Approved
0.8247	Intermediate Similarity	NPD2534	Approved
0.8247	Intermediate Similarity	NPD2533	Approved
0.8224	Intermediate Similarity	NPD7003	Approved
0.82	Intermediate Similarity	NPD2935	Discontinued
0.8133	Intermediate Similarity	NPD5844	Phase 1
0.8129	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1607	Approved
0.8095	Intermediate Similarity	NPD3764	Approved
0.8092	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD2346	Discontinued
0.8013	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1510	Phase 2
0.8013	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1240	Approved
0.7987	Intermediate Similarity	NPD3750	Approved
0.7977	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1201	Approved
0.7925	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7075	Discontinued
0.7875	Intermediate Similarity	NPD4380	Phase 2
0.7861	Intermediate Similarity	NPD8150	Discontinued
0.784	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7458	Discontinued
0.7791	Intermediate Similarity	NPD8312	Approved
0.7791	Intermediate Similarity	NPD8313	Approved
0.7778	Intermediate Similarity	NPD2799	Discontinued
0.7764	Intermediate Similarity	NPD6599	Discontinued
0.7755	Intermediate Similarity	NPD1164	Approved
0.7751	Intermediate Similarity	NPD7177	Discontinued
0.7748	Intermediate Similarity	NPD943	Approved
0.7744	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1549	Phase 2
0.7677	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2344	Approved
0.7674	Intermediate Similarity	NPD6559	Discontinued
0.7673	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6801	Discontinued
0.7662	Intermediate Similarity	NPD3748	Approved
0.7643	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD8151	Discontinued
0.7622	Intermediate Similarity	NPD2801	Approved
0.7619	Intermediate Similarity	NPD5710	Approved
0.7619	Intermediate Similarity	NPD5711	Approved
0.7613	Intermediate Similarity	NPD1551	Phase 2
0.7613	Intermediate Similarity	NPD2796	Approved
0.761	Intermediate Similarity	NPD6799	Approved
0.7598	Intermediate Similarity	NPD6534	Approved
0.7598	Intermediate Similarity	NPD6535	Approved
0.7568	Intermediate Similarity	NPD1283	Approved
0.7561	Intermediate Similarity	NPD1934	Approved
0.7554	Intermediate Similarity	NPD7435	Discontinued
0.7552	Intermediate Similarity	NPD9493	Approved
0.755	Intermediate Similarity	NPD7008	Discontinued
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.753	Intermediate Similarity	NPD3882	Suspended
0.7529	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6166	Phase 2
0.7529	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1465	Phase 2
0.7514	Intermediate Similarity	NPD8320	Phase 1
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.7514	Intermediate Similarity	NPD8319	Approved
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD1511	Approved
0.75	Intermediate Similarity	NPD5494	Approved
0.7486	Intermediate Similarity	NPD6777	Approved
0.7486	Intermediate Similarity	NPD6778	Approved
0.7486	Intermediate Similarity	NPD6779	Approved
0.7486	Intermediate Similarity	NPD6782	Approved
0.7486	Intermediate Similarity	NPD6776	Approved
0.7486	Intermediate Similarity	NPD6780	Approved
0.7486	Intermediate Similarity	NPD6781	Approved
0.7485	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2309	Approved
0.7473	Intermediate Similarity	NPD7700	Phase 2
0.7473	Intermediate Similarity	NPD7699	Phase 2
0.747	Intermediate Similarity	NPD3817	Phase 2
0.7469	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD920	Approved
0.7468	Intermediate Similarity	NPD1243	Approved
0.7468	Intermediate Similarity	NPD230	Phase 1
0.7448	Intermediate Similarity	NPD9545	Approved
0.7444	Intermediate Similarity	NPD6213	Phase 3
0.7444	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6212	Phase 3
0.7436	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD8166	Discontinued
0.7419	Intermediate Similarity	NPD7871	Phase 2
0.7419	Intermediate Similarity	NPD7870	Phase 2
0.7414	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7229	Phase 3
0.7407	Intermediate Similarity	NPD1512	Approved
0.7407	Intermediate Similarity	NPD6273	Approved
0.7366	Intermediate Similarity	NPD7698	Approved
0.7366	Intermediate Similarity	NPD7696	Phase 3
0.7366	Intermediate Similarity	NPD7697	Approved
0.7365	Intermediate Similarity	NPD5402	Approved
0.7365	Intermediate Similarity	NPD1281	Approved
0.7358	Intermediate Similarity	NPD2800	Approved
0.7351	Intermediate Similarity	NPD2798	Approved
0.7347	Intermediate Similarity	NPD4626	Approved
0.7346	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3818	Discontinued
0.7329	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7874	Approved
0.7308	Intermediate Similarity	NPD6651	Approved
0.7299	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7286	Phase 2
0.7285	Intermediate Similarity	NPD1203	Approved
0.7284	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1651	Approved
0.7278	Intermediate Similarity	NPD4287	Approved
0.7278	Intermediate Similarity	NPD6100	Approved
0.7278	Intermediate Similarity	NPD6099	Approved
0.7277	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7783	Phase 2
0.7273	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3926	Phase 2
0.7257	Intermediate Similarity	NPD7074	Phase 3
0.7256	Intermediate Similarity	NPD5403	Approved
0.7246	Intermediate Similarity	NPD37	Approved
0.7241	Intermediate Similarity	NPD3751	Discontinued
0.7235	Intermediate Similarity	NPD919	Approved
0.7233	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7211	Intermediate Similarity	NPD7701	Phase 2
0.7208	Intermediate Similarity	NPD4625	Phase 3
0.7208	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7054	Approved
0.72	Intermediate Similarity	NPD3972	Approved
0.7196	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2979	Phase 3
0.7172	Intermediate Similarity	NPD5951	Approved
0.7161	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD411	Approved
0.7161	Intermediate Similarity	NPD3268	Approved
0.716	Intermediate Similarity	NPD6190	Approved
0.7159	Intermediate Similarity	NPD7472	Approved
0.7158	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7135	Intermediate Similarity	NPD6234	Discontinued
0.7134	Intermediate Similarity	NPD5401	Approved
0.7128	Intermediate Similarity	NPD6823	Phase 2
0.7125	Intermediate Similarity	NPD1471	Phase 3
0.7119	Intermediate Similarity	NPD6797	Phase 2
0.7118	Intermediate Similarity	NPD4965	Approved
0.7118	Intermediate Similarity	NPD4966	Approved
0.7118	Intermediate Similarity	NPD4967	Phase 2
0.7117	Intermediate Similarity	NPD3300	Phase 2
0.7114	Intermediate Similarity	NPD3019	Approved
0.7114	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3787	Discontinued
0.7107	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7801	Approved
0.7086	Intermediate Similarity	NPD9717	Approved
0.7086	Intermediate Similarity	NPD1608	Approved
0.7079	Intermediate Similarity	NPD7251	Discontinued
0.7063	Intermediate Similarity	NPD2438	Suspended
0.7059	Intermediate Similarity	NPD2797	Approved
0.7059	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4288	Approved
0.7052	Intermediate Similarity	NPD7199	Phase 2
0.7047	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5691	Approved
0.7043	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7808	Phase 3
0.7039	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4908	Phase 1
0.7025	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD447	Suspended
0.7006	Intermediate Similarity	NPD6663	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