NPASS Compound

Structure

CID169452 OpenBabel06191715542D 25 27 0 0 0 0 0 0 0 0999 V2000 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 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 2.5981 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 0.8660 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 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 -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 -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 0.0000 -0.0000 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 11 1 0 0 0 0 6 13 2 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 12 1 0 0 0 0 10 17 2 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 24 2 0 0 0 0 20 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.13
Volume:	351.666
LogP:	5.543
LogD:	2.937
LogS:	-3.5
# Rotatable Bonds:	2
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.349
Synthetic Accessibility Score:	3.1
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.143
MDCK Permeability:	9.732555554364808e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.899

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	99.2867202758789%
Volume Distribution (VD):	0.514
Pgp-substrate:	3.6990926265716553%

ADMET: Metabolism

CYP1A2-inhibitor:	0.845
CYP1A2-substrate:	0.73
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.753
CYP2C9-substrate:	0.717
CYP2D6-inhibitor:	0.298
CYP2D6-substrate:	0.271
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	6.359
Half-life (T1/2):	0.563

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.892
AMES Toxicity:	0.706
Rat Oral Acute Toxicity:	0.157
Maximum Recommended Daily Dose:	0.855
Skin Sensitization:	0.957
Carcinogencity:	0.682
Eye Corrosion:	0.008
Eye Irritation:	0.919
Respiratory Toxicity:	0.256

Download Data

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

Natural Product: NPC169452

Natural Product ID:	NPC169452
*Common Name:**	Lupinacidin A
IUPAC Name:	1,3,5-trihydroxy-2-methyl-4-(3-methylbutyl)anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	WWUQQOQPOGZVSK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O5/c1-9(2)7-8-12-15-16(18(23)10(3)17(12)22)19(24)11-5-4-6-13(21)14(11)20(15)25/h4-6,9,21-23H,7-8H2,1-3H3
SMILES:	CC(C)CCc1c2c(c(c(C)c1O)O)C(=O)c1cccc(c1C2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL231549
PubChem CID:	23628280
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
NPO24286	Micromonospora lupini	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17475486]
NPO24286	Micromonospora lupini	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21226490]
NPO12925	Streptomyces spinoverrucosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23057874]
NPO12925	Streptomyces spinoverrucosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26489038]
NPO24286	Micromonospora lupini	Species	Micromonosporaceae	Bacteria	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	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2311	Cell Line	Calu-3	Homo sapiens	IC50	=	8800.0	nM	PMID[540242]
NPT2	Others	Unspecified		IC50	=	210.0	nM	PMID[540240]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	210.0	nM	PMID[540241]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3100.0	nM	PMID[540242]

☑ 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 NPC169452 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	387
0.1-0.2	1598
0.2-0.3	3560
0.3-0.4	9742
0.4-0.5	9425
0.5-0.6	4667
0.6-0.7	6532
0.7-0.8	5374
0.8-0.85	996
0.85-0.9	312
0.9-0.95	88
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC181560
0.9925	High Similarity	NPC242994
0.9925	High Similarity	NPC138099
0.9852	High Similarity	NPC193555
0.9774	High Similarity	NPC53414
0.9774	High Similarity	NPC471905
0.9774	High Similarity	NPC53206
0.9699	High Similarity	NPC254847
0.9562	High Similarity	NPC135524
0.9552	High Similarity	NPC191976
0.9549	High Similarity	NPC166480
0.9549	High Similarity	NPC44437
0.9549	High Similarity	NPC282780
0.9489	High Similarity	NPC204045
0.9489	High Similarity	NPC305845
0.9489	High Similarity	NPC246638
0.9485	High Similarity	NPC143438
0.9474	High Similarity	NPC267205
0.9424	High Similarity	NPC193703
0.9424	High Similarity	NPC21599
0.9357	High Similarity	NPC34482
0.9353	High Similarity	NPC474203
0.9353	High Similarity	NPC313047
0.9353	High Similarity	NPC295712
0.9353	High Similarity	NPC451542
0.9343	High Similarity	NPC190457
0.9291	High Similarity	NPC470570
0.9286	High Similarity	NPC244691
0.9286	High Similarity	NPC471906
0.9286	High Similarity	NPC48762
0.9281	High Similarity	NPC73061
0.9281	High Similarity	NPC474961
0.9265	High Similarity	NPC118919
0.9254	High Similarity	NPC175738
0.9225	High Similarity	NPC37709
0.9214	High Similarity	NPC293545
0.9214	High Similarity	NPC174905
0.9209	High Similarity	NPC290550
0.9191	High Similarity	NPC283088
0.9185	High Similarity	NPC115458
0.9173	High Similarity	NPC109123
0.9173	High Similarity	NPC92624
0.9173	High Similarity	NPC99731
0.9155	High Similarity	NPC85393
0.9155	High Similarity	NPC271944
0.9155	High Similarity	NPC110882
0.9137	High Similarity	NPC203063
0.913	High Similarity	NPC4214
0.913	High Similarity	NPC13715
0.9104	High Similarity	NPC259942
0.9098	High Similarity	NPC282923
0.9098	High Similarity	NPC473017
0.9091	High Similarity	NPC190648
0.9091	High Similarity	NPC118027
0.9091	High Similarity	NPC312929
0.9091	High Similarity	NPC126767
0.9091	High Similarity	NPC245584
0.9091	High Similarity	NPC289042
0.9091	High Similarity	NPC56433
0.9071	High Similarity	NPC187843
0.9065	High Similarity	NPC162939
0.9058	High Similarity	NPC53001
0.9051	High Similarity	NPC290803
0.9051	High Similarity	NPC161632
0.9034	High Similarity	NPC255641
0.9034	High Similarity	NPC290954
0.9034	High Similarity	NPC470568
0.903	High Similarity	NPC474998
0.9023	High Similarity	NPC169250
0.9023	High Similarity	NPC100067
0.9023	High Similarity	NPC266689
0.9023	High Similarity	NPC98254
0.9023	High Similarity	NPC23126
0.9023	High Similarity	NPC162612
0.9023	High Similarity	NPC103356
0.9023	High Similarity	NPC105157
0.9023	High Similarity	NPC30501
0.9023	High Similarity	NPC72158
0.9023	High Similarity	NPC190043
0.9014	High Similarity	NPC10764
0.9014	High Similarity	NPC227841
0.9007	High Similarity	NPC19631
0.9007	High Similarity	NPC239136
0.9007	High Similarity	NPC137649
0.8993	High Similarity	NPC416
0.8993	High Similarity	NPC87723
0.8993	High Similarity	NPC61398
0.8986	High Similarity	NPC272268
0.8978	High Similarity	NPC12070
0.8978	High Similarity	NPC50924
0.8973	High Similarity	NPC470569
0.8971	High Similarity	NPC58685
0.8966	High Similarity	NPC329933
0.8955	High Similarity	NPC21305
0.8955	High Similarity	NPC48248
0.8955	High Similarity	NPC221777
0.8951	High Similarity	NPC12402
0.8947	High Similarity	NPC62952
0.8947	High Similarity	NPC267846
0.8947	High Similarity	NPC8745
0.8944	High Similarity	NPC471682
0.8944	High Similarity	NPC238629
0.8944	High Similarity	NPC296752
0.8921	High Similarity	NPC290030
0.8919	High Similarity	NPC66508
0.8919	High Similarity	NPC226656
0.8913	High Similarity	NPC249272
0.8913	High Similarity	NPC80035
0.8912	High Similarity	NPC154683
0.8912	High Similarity	NPC40356
0.8905	High Similarity	NPC37299
0.8905	High Similarity	NPC114183
0.8905	High Similarity	NPC180261
0.8905	High Similarity	NPC225051
0.8905	High Similarity	NPC52407
0.8904	High Similarity	NPC147735
0.8904	High Similarity	NPC294646
0.8904	High Similarity	NPC205766
0.8897	High Similarity	NPC93015
0.8897	High Similarity	NPC205992
0.8881	High Similarity	NPC19896
0.8881	High Similarity	NPC116513
0.8873	High Similarity	NPC257644
0.8872	High Similarity	NPC103540
0.8872	High Similarity	NPC477454
0.8872	High Similarity	NPC10926
0.8865	High Similarity	NPC315578
0.8859	High Similarity	NPC470564
0.8851	High Similarity	NPC208806
0.8849	High Similarity	NPC194764
0.8849	High Similarity	NPC264112
0.8849	High Similarity	NPC65005
0.8844	High Similarity	NPC35
0.8841	High Similarity	NPC270899
0.8841	High Similarity	NPC475088
0.8836	High Similarity	NPC477221
0.8832	High Similarity	NPC70622
0.8828	High Similarity	NPC290194
0.8828	High Similarity	NPC34802
0.8824	High Similarity	NPC31799
0.8819	High Similarity	NPC471683
0.8819	High Similarity	NPC49282
0.8815	High Similarity	NPC96024
0.8811	High Similarity	NPC167663
0.8811	High Similarity	NPC66593
0.8806	High Similarity	NPC160499
0.8806	High Similarity	NPC3224
0.8806	High Similarity	NPC473691
0.8803	High Similarity	NPC110810
0.8797	High Similarity	NPC173978
0.8797	High Similarity	NPC142956
0.8797	High Similarity	NPC13238
0.8794	High Similarity	NPC472903
0.8794	High Similarity	NPC26924
0.8786	High Similarity	NPC474110
0.8786	High Similarity	NPC245923
0.8786	High Similarity	NPC44960
0.8777	High Similarity	NPC258502
0.8776	High Similarity	NPC280295
0.8768	High Similarity	NPC48036
0.8768	High Similarity	NPC53896
0.8768	High Similarity	NPC40524
0.8768	High Similarity	NPC139074
0.8768	High Similarity	NPC213485
0.8767	High Similarity	NPC471907
0.8759	High Similarity	NPC474517
0.8759	High Similarity	NPC475042
0.8759	High Similarity	NPC244699
0.8759	High Similarity	NPC72669
0.875	High Similarity	NPC146647
0.875	High Similarity	NPC276238
0.875	High Similarity	NPC34414
0.875	High Similarity	NPC303910
0.8742	High Similarity	NPC324736
0.8741	High Similarity	NPC49108
0.8741	High Similarity	NPC84672
0.8741	High Similarity	NPC69424
0.8741	High Similarity	NPC176130
0.8741	High Similarity	NPC78364
0.8732	High Similarity	NPC183345
0.8732	High Similarity	NPC109232
0.8731	High Similarity	NPC475733
0.8725	High Similarity	NPC107109
0.8725	High Similarity	NPC470408
0.8725	High Similarity	NPC214632
0.8725	High Similarity	NPC474824
0.8725	High Similarity	NPC182921
0.8725	High Similarity	NPC218870
0.8723	High Similarity	NPC20210
0.8723	High Similarity	NPC473622
0.8722	High Similarity	NPC65761
0.8722	High Similarity	NPC375356
0.8722	High Similarity	NPC472029
0.8714	High Similarity	NPC155211
0.8714	High Similarity	NPC474813
0.8707	High Similarity	NPC10027
0.8707	High Similarity	NPC65775
0.8705	High Similarity	NPC472262
0.8705	High Similarity	NPC288089
0.8705	High Similarity	NPC161964

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 NPC169452 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	950
0.2-0.3	1446
0.3-0.4	2736
0.4-0.5	2110
0.5-0.6	1056
0.6-0.7	373
0.7-0.8	111
0.8-0.85	10
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9699	High Similarity	NPD1509	Clinical (unspecified phase)
0.9014	High Similarity	NPD7390	Discontinued
0.8872	High Similarity	NPD1470	Approved
0.8652	High Similarity	NPD5406	Approved
0.8652	High Similarity	NPD5404	Approved
0.8652	High Similarity	NPD5408	Approved
0.8652	High Similarity	NPD5405	Approved
0.8571	High Similarity	NPD1201	Approved
0.8561	High Similarity	NPD943	Approved
0.8408	Intermediate Similarity	NPD7473	Discontinued
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8194	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1607	Approved
0.8117	Intermediate Similarity	NPD7819	Suspended
0.8069	Intermediate Similarity	NPD1510	Phase 2
0.8067	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD1240	Approved
0.8038	Intermediate Similarity	NPD6959	Discontinued
0.7985	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD3226	Approved
0.7949	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD2534	Approved
0.7947	Intermediate Similarity	NPD2532	Approved
0.7947	Intermediate Similarity	NPD2533	Approved
0.7905	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD4380	Phase 2
0.7801	Intermediate Similarity	NPD1164	Approved
0.7785	Intermediate Similarity	NPD1549	Phase 2
0.777	Intermediate Similarity	NPD2935	Discontinued
0.7756	Intermediate Similarity	NPD7411	Suspended
0.7754	Intermediate Similarity	NPD3019	Approved
0.7736	Intermediate Similarity	NPD3749	Approved
0.7718	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2346	Discontinued
0.7718	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD3750	Approved
0.7658	Intermediate Similarity	NPD2801	Approved
0.7651	Intermediate Similarity	NPD2796	Approved
0.7647	Intermediate Similarity	NPD1511	Approved
0.7636	Intermediate Similarity	NPD6020	Phase 2
0.7626	Intermediate Similarity	NPD2932	Approved
0.7625	Intermediate Similarity	NPD7075	Discontinued
0.7595	Intermediate Similarity	NPD1934	Approved
0.7584	Intermediate Similarity	NPD2799	Discontinued
0.7584	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD3300	Phase 2
0.7562	Intermediate Similarity	NPD7768	Phase 2
0.7562	Intermediate Similarity	NPD3882	Suspended
0.7561	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1512	Approved
0.7547	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3764	Approved
0.7533	Intermediate Similarity	NPD6100	Approved
0.7533	Intermediate Similarity	NPD6099	Approved
0.7531	Intermediate Similarity	NPD5494	Approved
0.753	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD2800	Approved
0.7483	Intermediate Similarity	NPD2344	Approved
0.7468	Intermediate Similarity	NPD6599	Discontinued
0.7463	Intermediate Similarity	NPD4750	Phase 3
0.7451	Intermediate Similarity	NPD7003	Approved
0.745	Intermediate Similarity	NPD6651	Approved
0.7414	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD8150	Discontinued
0.7379	Intermediate Similarity	NPD2798	Approved
0.7375	Intermediate Similarity	NPD6801	Discontinued
0.7351	Intermediate Similarity	NPD3748	Approved
0.7349	Intermediate Similarity	NPD6166	Phase 2
0.7349	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD9269	Phase 2
0.7338	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5710	Approved
0.7333	Intermediate Similarity	NPD5711	Approved
0.7324	Intermediate Similarity	NPD3023	Approved
0.7324	Intermediate Similarity	NPD3026	Approved
0.7319	Intermediate Similarity	NPD5951	Approved
0.7308	Intermediate Similarity	NPD6799	Approved
0.7305	Intermediate Similarity	NPD9268	Approved
0.7305	Intermediate Similarity	NPD3024	Approved
0.7305	Intermediate Similarity	NPD3025	Approved
0.7303	Intermediate Similarity	NPD1551	Phase 2
0.7301	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7458	Discontinued
0.7294	Intermediate Similarity	NPD6559	Discontinued
0.729	Intermediate Similarity	NPD2309	Approved
0.7262	Intermediate Similarity	NPD3818	Discontinued
0.7239	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5953	Discontinued
0.7232	Intermediate Similarity	NPD6535	Approved
0.7232	Intermediate Similarity	NPD6534	Approved
0.723	Intermediate Similarity	NPD4625	Phase 3
0.7185	Intermediate Similarity	NPD2342	Discontinued
0.7181	Intermediate Similarity	NPD2313	Discontinued
0.7178	Intermediate Similarity	NPD3817	Phase 2
0.7174	Intermediate Similarity	NPD7635	Approved
0.7161	Intermediate Similarity	NPD1243	Approved
0.7152	Intermediate Similarity	NPD230	Phase 1
0.7151	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7132	Intermediate Similarity	NPD74	Approved
0.7132	Intermediate Similarity	NPD9266	Approved
0.7127	Intermediate Similarity	NPD6780	Approved
0.7127	Intermediate Similarity	NPD6778	Approved
0.7127	Intermediate Similarity	NPD6776	Approved
0.7127	Intermediate Similarity	NPD6782	Approved
0.7127	Intermediate Similarity	NPD6779	Approved
0.7127	Intermediate Similarity	NPD6781	Approved
0.7127	Intermediate Similarity	NPD6777	Approved
0.7123	Intermediate Similarity	NPD1283	Approved
0.7118	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1465	Phase 2
0.7111	Intermediate Similarity	NPD7699	Phase 2
0.7111	Intermediate Similarity	NPD7700	Phase 2
0.711	Intermediate Similarity	NPD8313	Approved
0.711	Intermediate Similarity	NPD8312	Approved
0.7103	Intermediate Similarity	NPD3972	Approved
0.7102	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD9493	Approved
0.7083	Intermediate Similarity	NPD3926	Phase 2
0.7076	Intermediate Similarity	NPD7074	Phase 3
0.7073	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD940	Approved
0.7068	Intermediate Similarity	NPD846	Approved
0.7067	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8320	Phase 1
0.7065	Intermediate Similarity	NPD8319	Approved
0.7063	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1651	Approved
0.7063	Intermediate Similarity	NPD920	Approved
0.7059	Intermediate Similarity	NPD9267	Approved
0.7059	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9263	Approved
0.7059	Intermediate Similarity	NPD9264	Approved
0.7055	Intermediate Similarity	NPD37	Approved
0.7033	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7229	Phase 3
0.702	Intermediate Similarity	NPD6663	Approved
0.7018	Intermediate Similarity	NPD7286	Phase 2
0.7018	Intermediate Similarity	NPD7054	Approved
0.7014	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7697	Approved
0.7011	Intermediate Similarity	NPD7696	Phase 3
0.7011	Intermediate Similarity	NPD7435	Discontinued
0.7011	Intermediate Similarity	NPD7698	Approved
0.7007	Intermediate Similarity	NPD1876	Approved
0.7006	Intermediate Similarity	NPD4628	Phase 3
0.7006	Intermediate Similarity	NPD8166	Discontinued
0.7005	Intermediate Similarity	NPD8151	Discontinued
0.6992	Remote Similarity	NPD1242	Phase 1
0.6986	Remote Similarity	NPD4878	Approved
0.6983	Remote Similarity	NPD6212	Phase 3
0.6983	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6213	Phase 3
0.698	Remote Similarity	NPD5736	Approved
0.6977	Remote Similarity	NPD7472	Approved
0.6973	Remote Similarity	NPD7871	Phase 2
0.6973	Remote Similarity	NPD7870	Phase 2
0.697	Remote Similarity	NPD5402	Approved
0.6959	Remote Similarity	NPD1203	Approved
0.6954	Remote Similarity	NPD3268	Approved
0.6954	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6234	Discontinued
0.6937	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6797	Phase 2
0.6933	Remote Similarity	NPD4908	Phase 1
0.6928	Remote Similarity	NPD4966	Approved
0.6928	Remote Similarity	NPD4965	Approved
0.6928	Remote Similarity	NPD4967	Phase 2
0.6918	Remote Similarity	NPD1281	Approved
0.6918	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3020	Approved
0.6903	Remote Similarity	NPD4308	Phase 3
0.6898	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7251	Discontinued
0.6897	Remote Similarity	NPD4626	Approved
0.6894	Remote Similarity	NPD6273	Approved
0.6875	Remote Similarity	NPD9545	Approved
0.6875	Remote Similarity	NPD3091	Approved
0.6864	Remote Similarity	NPD1247	Approved
0.6862	Remote Similarity	NPD7701	Phase 2
0.686	Remote Similarity	NPD3751	Discontinued
0.686	Remote Similarity	NPD7177	Discontinued
0.6857	Remote Similarity	NPD7808	Phase 3
0.6857	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6190	Approved
0.6852	Remote Similarity	NPD5403	Approved
0.6846	Remote Similarity	NPD3094	Phase 2
0.6846	Remote Similarity	NPD2797	Approved
0.6845	Remote Similarity	NPD919	Approved
0.6845	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7801	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