NPASS Compound

Structure

NPC242994 OpenBabel07101719512D 24 26 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 -0.0000 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 3.5000 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 -1.7321 3.0000 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 1.5000 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 3 1 0 0 0 0 2 9 1 0 0 0 0 3 4 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 8 12 2 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 19 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.12
Volume:	334.37
LogP:	5.344
LogD:	2.824
LogS:	-3.429
# 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:	0.358
Synthetic Accessibility Score:	3.07
Fsp3:	0.158
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:	-5.102
MDCK Permeability:	9.781856533663813e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.15
20% Bioavailability (F20%):	0.126
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	99.31901550292969%
Volume Distribution (VD):	0.504
Pgp-substrate:	4.1159467697143555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.892
CYP1A2-substrate:	0.74
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.661
CYP2C9-substrate:	0.71
CYP2D6-inhibitor:	0.252
CYP2D6-substrate:	0.405
CYP3A4-inhibitor:	0.072
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	5.819
Half-life (T1/2):	0.677

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.812
AMES Toxicity:	0.688
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.758
Skin Sensitization:	0.96
Carcinogencity:	0.641
Eye Corrosion:	0.014
Eye Irritation:	0.918
Respiratory Toxicity:	0.251

Download Data

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

Natural Product: NPC242994

Natural Product ID:	NPC242994
*Common Name:**	Lupinacidin B
IUPAC Name:	4-butyl-1,3,5-trihydroxy-2-methylanthracene-9,10-dione
Synonyms:	Lupinacidins B
Standard InCHIKey:	IVQKRDHUECCAJE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O5/c1-3-4-6-11-14-15(17(22)9(2)16(11)21)18(23)10-7-5-8-12(20)13(10)19(14)24/h5,7-8,20-22H,3-4,6H2,1-2H3
SMILES:	CCCCc1c2c(C(=O)c3c(C2=O)c(O)ccc3)c(c(c1O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL231553
PubChem CID:	23628281
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]
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	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	920.0	nM	PMID[480396]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	920.0	nM	PMID[480397]

☑ 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 NPC242994 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	384
0.1-0.2	1722
0.2-0.3	3909
0.3-0.4	10708
0.4-0.5	8195
0.5-0.6	4860
0.6-0.7	6191
0.7-0.8	5290
0.8-0.85	1012
0.85-0.9	314
0.9-0.95	87
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC138099
0.9925	High Similarity	NPC181560
0.9925	High Similarity	NPC169452
0.9848	High Similarity	NPC471905
0.9848	High Similarity	NPC53206
0.9848	High Similarity	NPC53414
0.9778	High Similarity	NPC193555
0.9773	High Similarity	NPC254847
0.9632	High Similarity	NPC135524
0.9624	High Similarity	NPC191976
0.9621	High Similarity	NPC166480
0.9621	High Similarity	NPC44437
0.9621	High Similarity	NPC282780
0.9559	High Similarity	NPC246638
0.9559	High Similarity	NPC204045
0.9559	High Similarity	NPC305845
0.9556	High Similarity	NPC143438
0.9545	High Similarity	NPC267205
0.9493	High Similarity	NPC21599
0.9493	High Similarity	NPC193703
0.9424	High Similarity	NPC34482
0.9412	High Similarity	NPC190457
0.9357	High Similarity	NPC470570
0.9353	High Similarity	NPC471906
0.9353	High Similarity	NPC48762
0.9353	High Similarity	NPC244691
0.9348	High Similarity	NPC73061
0.9348	High Similarity	NPC474961
0.9333	High Similarity	NPC118919
0.9291	High Similarity	NPC37709
0.9281	High Similarity	NPC313047
0.9281	High Similarity	NPC451542
0.9281	High Similarity	NPC295712
0.9281	High Similarity	NPC474203
0.9275	High Similarity	NPC290550
0.9259	High Similarity	NPC283088
0.9242	High Similarity	NPC92624
0.9242	High Similarity	NPC99731
0.9203	High Similarity	NPC203063
0.9197	High Similarity	NPC4214
0.9197	High Similarity	NPC13715
0.9179	High Similarity	NPC175738
0.9173	High Similarity	NPC259942
0.9167	High Similarity	NPC282923
0.9155	High Similarity	NPC118027
0.9155	High Similarity	NPC190648
0.9155	High Similarity	NPC126767
0.9155	High Similarity	NPC245584
0.9155	High Similarity	NPC56433
0.9155	High Similarity	NPC312929
0.9155	High Similarity	NPC289042
0.9143	High Similarity	NPC174905
0.9143	High Similarity	NPC293545
0.9137	High Similarity	NPC187843
0.9124	High Similarity	NPC53001
0.9118	High Similarity	NPC161632
0.9111	High Similarity	NPC115458
0.9098	High Similarity	NPC474998
0.9098	High Similarity	NPC109123
0.9097	High Similarity	NPC470568
0.9097	High Similarity	NPC255641
0.9097	High Similarity	NPC290954
0.9091	High Similarity	NPC105157
0.9091	High Similarity	NPC162612
0.9091	High Similarity	NPC30501
0.9091	High Similarity	NPC103356
0.9091	High Similarity	NPC72158
0.9091	High Similarity	NPC266689
0.9091	High Similarity	NPC169250
0.9091	High Similarity	NPC100067
0.9091	High Similarity	NPC190043
0.9091	High Similarity	NPC98254
0.9091	High Similarity	NPC23126
0.9085	High Similarity	NPC271944
0.9085	High Similarity	NPC110882
0.9085	High Similarity	NPC85393
0.9078	High Similarity	NPC10764
0.9078	High Similarity	NPC227841
0.9071	High Similarity	NPC19631
0.9071	High Similarity	NPC239136
0.9058	High Similarity	NPC61398
0.9058	High Similarity	NPC87723
0.9058	High Similarity	NPC416
0.9044	High Similarity	NPC12070
0.9044	High Similarity	NPC50924
0.9034	High Similarity	NPC470569
0.9023	High Similarity	NPC221777
0.9023	High Similarity	NPC48248
0.9023	High Similarity	NPC473017
0.9023	High Similarity	NPC21305
0.9015	High Similarity	NPC8745
0.9015	High Similarity	NPC62952
0.9015	High Similarity	NPC267846
0.9014	High Similarity	NPC12402
0.9007	High Similarity	NPC471682
0.9007	High Similarity	NPC238629
0.9007	High Similarity	NPC296752
0.8993	High Similarity	NPC162939
0.8986	High Similarity	NPC290030
0.898	High Similarity	NPC226656
0.898	High Similarity	NPC66508
0.8978	High Similarity	NPC290803
0.8978	High Similarity	NPC80035
0.8978	High Similarity	NPC249272
0.8973	High Similarity	NPC154683
0.8973	High Similarity	NPC40356
0.8971	High Similarity	NPC225051
0.8971	High Similarity	NPC114183
0.8971	High Similarity	NPC52407
0.8971	High Similarity	NPC37299
0.8971	High Similarity	NPC180261
0.8966	High Similarity	NPC147735
0.8966	High Similarity	NPC294646
0.8966	High Similarity	NPC205766
0.8963	High Similarity	NPC205992
0.8963	High Similarity	NPC93015
0.8947	High Similarity	NPC116513
0.8944	High Similarity	NPC19896
0.8939	High Similarity	NPC103540
0.8939	High Similarity	NPC477454
0.8939	High Similarity	NPC10926
0.8936	High Similarity	NPC257644
0.8936	High Similarity	NPC137649
0.8929	High Similarity	NPC315578
0.8919	High Similarity	NPC470564
0.8913	High Similarity	NPC194764
0.8913	High Similarity	NPC272268
0.8913	High Similarity	NPC264112
0.8913	High Similarity	NPC65005
0.8912	High Similarity	NPC208806
0.8905	High Similarity	NPC270899
0.8904	High Similarity	NPC35
0.8897	High Similarity	NPC70622
0.8897	High Similarity	NPC329933
0.8897	High Similarity	NPC58685
0.8889	High Similarity	NPC34802
0.8889	High Similarity	NPC31799
0.8889	High Similarity	NPC290194
0.8881	High Similarity	NPC49282
0.8881	High Similarity	NPC471683
0.8873	High Similarity	NPC66593
0.8873	High Similarity	NPC167663
0.8872	High Similarity	NPC473691
0.8872	High Similarity	NPC160499
0.8865	High Similarity	NPC110810
0.8864	High Similarity	NPC142956
0.8864	High Similarity	NPC13238
0.8864	High Similarity	NPC173978
0.8857	High Similarity	NPC26924
0.8857	High Similarity	NPC472903
0.8849	High Similarity	NPC245923
0.8849	High Similarity	NPC474110
0.8849	High Similarity	NPC44960
0.8841	High Similarity	NPC258502
0.8836	High Similarity	NPC280295
0.8832	High Similarity	NPC139074
0.8832	High Similarity	NPC48036
0.8832	High Similarity	NPC40524
0.8832	High Similarity	NPC53896
0.8832	High Similarity	NPC213485
0.8828	High Similarity	NPC471907
0.8824	High Similarity	NPC474517
0.8824	High Similarity	NPC475042
0.8824	High Similarity	NPC72669
0.8824	High Similarity	NPC244699
0.8815	High Similarity	NPC146647
0.8815	High Similarity	NPC34414
0.8803	High Similarity	NPC49108
0.88	High Similarity	NPC324736
0.8794	High Similarity	NPC183345
0.8788	High Similarity	NPC375356
0.8784	High Similarity	NPC214632
0.8784	High Similarity	NPC107109
0.8777	High Similarity	NPC474813
0.8777	High Similarity	NPC155211
0.8768	High Similarity	NPC475088
0.8768	High Similarity	NPC288089
0.8768	High Similarity	NPC474519
0.8767	High Similarity	NPC477221
0.8767	High Similarity	NPC10027
0.8767	High Similarity	NPC65775
0.875	High Similarity	NPC199253
0.875	High Similarity	NPC247477
0.875	High Similarity	NPC478019
0.875	High Similarity	NPC136588
0.875	High Similarity	NPC62219
0.875	High Similarity	NPC17840
0.8741	High Similarity	NPC179898
0.8741	High Similarity	NPC84266
0.8741	High Similarity	NPC96024
0.8733	High Similarity	NPC199463
0.8733	High Similarity	NPC178976
0.8733	High Similarity	NPC37543
0.8732	High Similarity	NPC472904
0.8731	High Similarity	NPC3224
0.8725	High Similarity	NPC66029
0.8714	High Similarity	NPC62272
0.8712	High Similarity	NPC300274
0.8712	High Similarity	NPC309765
0.8712	High Similarity	NPC133909

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 NPC242994 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	972
0.2-0.3	1444
0.3-0.4	2818
0.4-0.5	2053
0.5-0.6	1032
0.6-0.7	336
0.7-0.8	112
0.8-0.85	9
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9773	High Similarity	NPD1509	Clinical (unspecified phase)
0.9078	High Similarity	NPD7390	Discontinued
0.8939	High Similarity	NPD1470	Approved
0.8714	High Similarity	NPD5406	Approved
0.8714	High Similarity	NPD5408	Approved
0.8714	High Similarity	NPD5405	Approved
0.8714	High Similarity	NPD5404	Approved
0.8636	High Similarity	NPD1201	Approved
0.8623	High Similarity	NPD943	Approved
0.8387	Intermediate Similarity	NPD6232	Discontinued
0.8344	Intermediate Similarity	NPD7473	Discontinued
0.8252	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1607	Approved
0.817	Intermediate Similarity	NPD7819	Suspended
0.8125	Intermediate Similarity	NPD1510	Phase 2
0.8121	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD1240	Approved
0.8089	Intermediate Similarity	NPD6959	Discontinued
0.8045	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2532	Approved
0.7935	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4380	Phase 2
0.7857	Intermediate Similarity	NPD1164	Approved
0.7838	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1549	Phase 2
0.7823	Intermediate Similarity	NPD2935	Discontinued
0.7806	Intermediate Similarity	NPD7411	Suspended
0.7785	Intermediate Similarity	NPD3749	Approved
0.777	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2346	Discontinued
0.7733	Intermediate Similarity	NPD3750	Approved
0.7707	Intermediate Similarity	NPD2801	Approved
0.7703	Intermediate Similarity	NPD2796	Approved
0.7697	Intermediate Similarity	NPD1511	Approved
0.7681	Intermediate Similarity	NPD3019	Approved
0.7673	Intermediate Similarity	NPD7075	Discontinued
0.7643	Intermediate Similarity	NPD1934	Approved
0.761	Intermediate Similarity	NPD7768	Phase 2
0.761	Intermediate Similarity	NPD3882	Suspended
0.7609	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1512	Approved
0.7595	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3764	Approved
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7576	Intermediate Similarity	NPD6020	Phase 2
0.7554	Intermediate Similarity	NPD2932	Approved
0.755	Intermediate Similarity	NPD2800	Approved
0.7533	Intermediate Similarity	NPD2344	Approved
0.7517	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD3300	Phase 2
0.7516	Intermediate Similarity	NPD6599	Discontinued
0.7469	Intermediate Similarity	NPD5494	Approved
0.7467	Intermediate Similarity	NPD6099	Approved
0.7467	Intermediate Similarity	NPD6100	Approved
0.7457	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6801	Discontinued
0.74	Intermediate Similarity	NPD3748	Approved
0.7394	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6166	Phase 2
0.7394	Intermediate Similarity	NPD9269	Phase 2
0.7388	Intermediate Similarity	NPD4750	Phase 3
0.7386	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7003	Approved
0.7383	Intermediate Similarity	NPD6651	Approved
0.7378	Intermediate Similarity	NPD5710	Approved
0.7378	Intermediate Similarity	NPD5711	Approved
0.7372	Intermediate Similarity	NPD5951	Approved
0.7357	Intermediate Similarity	NPD9268	Approved
0.7355	Intermediate Similarity	NPD6799	Approved
0.7351	Intermediate Similarity	NPD1551	Phase 2
0.7346	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2309	Approved
0.7337	Intermediate Similarity	NPD6559	Discontinued
0.7326	Intermediate Similarity	NPD8150	Discontinued
0.731	Intermediate Similarity	NPD2798	Approved
0.7305	Intermediate Similarity	NPD3818	Discontinued
0.7284	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4625	Phase 3
0.7278	Intermediate Similarity	NPD5953	Discontinued
0.7273	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6534	Approved
0.7273	Intermediate Similarity	NPD6535	Approved
0.7254	Intermediate Similarity	NPD3026	Approved
0.7254	Intermediate Similarity	NPD3023	Approved
0.7239	Intermediate Similarity	NPD2342	Discontinued
0.7234	Intermediate Similarity	NPD3024	Approved
0.7234	Intermediate Similarity	NPD3025	Approved
0.7233	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7458	Discontinued
0.723	Intermediate Similarity	NPD2313	Discontinued
0.7222	Intermediate Similarity	NPD3817	Phase 2
0.7208	Intermediate Similarity	NPD1243	Approved
0.72	Intermediate Similarity	NPD230	Phase 1
0.719	Intermediate Similarity	NPD1471	Phase 3
0.7185	Intermediate Similarity	NPD9266	Approved
0.7185	Intermediate Similarity	NPD74	Approved
0.7167	Intermediate Similarity	NPD6777	Approved
0.7167	Intermediate Similarity	NPD6776	Approved
0.7167	Intermediate Similarity	NPD6780	Approved
0.7167	Intermediate Similarity	NPD6782	Approved
0.7167	Intermediate Similarity	NPD6779	Approved
0.7167	Intermediate Similarity	NPD6778	Approved
0.7167	Intermediate Similarity	NPD6781	Approved
0.716	Intermediate Similarity	NPD1465	Phase 2
0.716	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3972	Approved
0.7151	Intermediate Similarity	NPD7699	Phase 2
0.7151	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9493	Approved
0.7126	Intermediate Similarity	NPD3926	Phase 2
0.7121	Intermediate Similarity	NPD940	Approved
0.7121	Intermediate Similarity	NPD846	Approved
0.7118	Intermediate Similarity	NPD7074	Phase 3
0.7113	Intermediate Similarity	NPD1651	Approved
0.7111	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD9267	Approved
0.7111	Intermediate Similarity	NPD9263	Approved
0.7111	Intermediate Similarity	NPD9264	Approved
0.7107	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD920	Approved
0.7101	Intermediate Similarity	NPD7635	Approved
0.7093	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7286	Phase 2
0.7059	Intermediate Similarity	NPD7054	Approved
0.7055	Intermediate Similarity	NPD1283	Approved
0.7052	Intermediate Similarity	NPD8313	Approved
0.7052	Intermediate Similarity	NPD8312	Approved
0.7051	Intermediate Similarity	NPD4628	Phase 3
0.7049	Intermediate Similarity	NPD7696	Phase 3
0.7049	Intermediate Similarity	NPD7698	Approved
0.7049	Intermediate Similarity	NPD7697	Approved
0.7049	Intermediate Similarity	NPD7435	Discontinued
0.7045	Intermediate Similarity	NPD1242	Phase 1
0.7043	Intermediate Similarity	NPD8151	Discontinued
0.7022	Intermediate Similarity	NPD6212	Phase 3
0.7022	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6213	Phase 3
0.7018	Intermediate Similarity	NPD7472	Approved
0.7012	Intermediate Similarity	NPD5402	Approved
0.7012	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7870	Phase 2
0.7011	Intermediate Similarity	NPD7871	Phase 2
0.7011	Intermediate Similarity	NPD8320	Phase 1
0.7011	Intermediate Similarity	NPD8319	Approved
0.7007	Intermediate Similarity	NPD1203	Approved
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD37	Approved
0.6981	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6797	Phase 2
0.6964	Remote Similarity	NPD7229	Phase 3
0.6962	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6663	Approved
0.6948	Remote Similarity	NPD4308	Phase 3
0.6944	Remote Similarity	NPD4626	Approved
0.6943	Remote Similarity	NPD8166	Discontinued
0.6939	Remote Similarity	NPD1876	Approved
0.6936	Remote Similarity	NPD7251	Discontinued
0.6935	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9545	Approved
0.6918	Remote Similarity	NPD4878	Approved
0.6913	Remote Similarity	NPD5736	Approved
0.6905	Remote Similarity	NPD1247	Approved
0.6901	Remote Similarity	NPD3751	Discontinued
0.6901	Remote Similarity	NPD7177	Discontinued
0.6899	Remote Similarity	NPD6190	Approved
0.6898	Remote Similarity	NPD7701	Phase 2
0.6897	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7808	Phase 3
0.6894	Remote Similarity	NPD5403	Approved
0.6887	Remote Similarity	NPD411	Approved
0.6887	Remote Similarity	NPD3268	Approved
0.6886	Remote Similarity	NPD919	Approved
0.6886	Remote Similarity	NPD6234	Discontinued
0.6882	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD9281	Approved
0.6875	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4966	Approved
0.6867	Remote Similarity	NPD4965	Approved
0.6867	Remote Similarity	NPD4908	Phase 1
0.6867	Remote Similarity	NPD4967	Phase 2
0.6854	Remote Similarity	NPD4287	Approved
0.6849	Remote Similarity	NPD1281	Approved
0.6842	Remote Similarity	NPD3020	Approved
0.6832	Remote Similarity	NPD6273	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