NPASS Compound

Structure

NPC305845 OpenBabel07101718182D 23 25 0 0 1 0 0 0 0 0999 V2000 -5.1962 -2.0000 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 -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 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 -4.3301 -1.5000 0.0000 C 0 0 1 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 -1.7321 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 -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 -0.0000 -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 -4.3301 -0.5000 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 1.7321 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 7 1 0 0 0 0 2 8 1 0 0 0 0 3 8 2 0 0 0 0 3 10 1 0 0 0 0 4 8 1 0 0 0 0 4 12 2 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 13 2 0 0 0 0 7 1 1 6 0 0 0 7 18 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 15 17 1 0 0 0 0 16 22 2 0 0 0 0 17 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	308.569
LogP:	2.44
LogD:	1.576
LogS:	-3.504
# Rotatable Bonds:	2
TPSA:	118.22
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.366
Synthetic Accessibility Score:	2.816
Fsp3:	0.118
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:	-5.473
MDCK Permeability:	4.454480404092465e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.293
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	94.70903778076172%
Volume Distribution (VD):	0.555
Pgp-substrate:	8.500825881958008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.434
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.606
CYP2C9-substrate:	0.723
CYP2D6-inhibitor:	0.184
CYP2D6-substrate:	0.211
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.089

ADMET: Excretion

Clearance (CL):	13.339
Half-life (T1/2):	0.925

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.238
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.575
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.808
Skin Sensitization:	0.941
Carcinogencity:	0.026
Eye Corrosion:	0.005
Eye Irritation:	0.921
Respiratory Toxicity:	0.066

Download Data

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

Natural Product: NPC305845

Natural Product ID:	NPC305845
*Common Name:**	(+)-2's-Isorhodoptilometrin
IUPAC Name:	1,3,8-trihydroxy-6-[(2S)-2-hydroxypropyl]anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	LCYTUQNPPBLNJZ-ZETCQYMHSA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-7(18)2-8-3-10-14(12(20)4-8)17(23)15-11(16(10)22)5-9(19)6-13(15)21/h3-7,18-21H,2H2,1H3/t7-/m0/s1
SMILES:	C[C@@H](Cc1cc2c(c(c1)O)C(=O)c1c(cc(cc1O)O)C2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3289786
PubChem CID:	51537215
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
NPO472	Penicillium restrictum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24911880]
NPO472	Penicillium restrictum	Species	Aspergillaceae	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
NPT4782	Individual Protein	Accessory gene regulator protein A	Staphylococcus aureus	IC50	=	8900.0	nM	PMID[553234]

☑ 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 NPC305845 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	357
0.1-0.2	1514
0.2-0.3	3562
0.3-0.4	9154
0.4-0.5	10072
0.5-0.6	4597
0.6-0.7	6341
0.7-0.8	5676
0.8-0.85	1075
0.85-0.9	272
0.9-0.95	61
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC204045
0.9926	High Similarity	NPC135524
0.9781	High Similarity	NPC244691
0.9781	High Similarity	NPC471906
0.9704	High Similarity	NPC190457
0.9701	High Similarity	NPC471905
0.9638	High Similarity	NPC48762
0.9635	High Similarity	NPC474961
0.9627	High Similarity	NPC254847
0.9568	High Similarity	NPC34482
0.9559	High Similarity	NPC138099
0.9559	High Similarity	NPC242994
0.9556	High Similarity	NPC53414
0.9556	High Similarity	NPC53206
0.95	High Similarity	NPC470570
0.9496	High Similarity	NPC21599
0.9496	High Similarity	NPC193703
0.9489	High Similarity	NPC169452
0.9489	High Similarity	NPC181560
0.942	High Similarity	NPC246638
0.9416	High Similarity	NPC143438
0.9403	High Similarity	NPC267205
0.9353	High Similarity	NPC73061
0.9353	High Similarity	NPC193555
0.9338	High Similarity	NPC191976
0.9333	High Similarity	NPC44437
0.9306	High Similarity	NPC470569
0.9236	High Similarity	NPC290954
0.9236	High Similarity	NPC470568
0.9236	High Similarity	NPC147735
0.9236	High Similarity	NPC255641
0.9191	High Similarity	NPC282780
0.9191	High Similarity	NPC166480
0.9161	High Similarity	NPC312929
0.9161	High Similarity	NPC56433
0.9161	High Similarity	NPC245584
0.9161	High Similarity	NPC289042
0.9161	High Similarity	NPC118027
0.9161	High Similarity	NPC190648
0.9161	High Similarity	NPC126767
0.9143	High Similarity	NPC290550
0.9118	High Similarity	NPC314048
0.9118	High Similarity	NPC52407
0.9111	High Similarity	NPC93015
0.9103	High Similarity	NPC280295
0.9078	High Similarity	NPC137649
0.9058	High Similarity	NPC315275
0.9044	High Similarity	NPC70622
0.9037	High Similarity	NPC147757
0.9037	High Similarity	NPC31799
0.9034	High Similarity	NPC477221
0.9028	High Similarity	NPC290194
0.9028	High Similarity	NPC37709
0.9007	High Similarity	NPC187843
0.898	High Similarity	NPC154683
0.898	High Similarity	NPC40356
0.8978	High Similarity	NPC139074
0.8978	High Similarity	NPC213485
0.8978	High Similarity	NPC40524
0.8973	High Similarity	NPC294646
0.8971	High Similarity	NPC475042
0.8963	High Similarity	NPC99731
0.8951	High Similarity	NPC19896
0.8936	High Similarity	NPC203063
0.8929	High Similarity	NPC13715
0.8929	High Similarity	NPC4214
0.8921	High Similarity	NPC118919
0.8919	High Similarity	NPC208806
0.8913	High Similarity	NPC474519
0.8905	High Similarity	NPC478190
0.8897	High Similarity	NPC136588
0.8897	High Similarity	NPC199253
0.8897	High Similarity	NPC62219
0.8889	High Similarity	NPC282923
0.8881	High Similarity	NPC295712
0.8881	High Similarity	NPC313047
0.8881	High Similarity	NPC474203
0.8881	High Similarity	NPC451542
0.8881	High Similarity	NPC174905
0.8881	High Similarity	NPC293545
0.8873	High Similarity	NPC110810
0.8865	High Similarity	NPC162939
0.8857	High Similarity	NPC53001
0.8849	High Similarity	NPC61153
0.8849	High Similarity	NPC130899
0.8849	High Similarity	NPC161632
0.8849	High Similarity	NPC283590
0.8849	High Similarity	NPC283088
0.8849	High Similarity	NPC70859
0.8828	High Similarity	NPC143685
0.8828	High Similarity	NPC314437
0.8824	High Similarity	NPC92624
0.8819	High Similarity	NPC227841
0.8811	High Similarity	NPC469520
0.8808	High Similarity	NPC470559
0.8808	High Similarity	NPC324736
0.8806	High Similarity	NPC10926
0.8803	High Similarity	NPC156872
0.8803	High Similarity	NPC183345
0.8794	High Similarity	NPC87723
0.8794	High Similarity	NPC416
0.8794	High Similarity	NPC61398
0.8792	High Similarity	NPC470408
0.8792	High Similarity	NPC472211
0.8792	High Similarity	NPC182921
0.8792	High Similarity	NPC474824
0.8792	High Similarity	NPC218870
0.8792	High Similarity	NPC107109
0.8777	High Similarity	NPC474394
0.8777	High Similarity	NPC50924
0.8777	High Similarity	NPC12070
0.8768	High Similarity	NPC175738
0.8767	High Similarity	NPC34802
0.8759	High Similarity	NPC49282
0.8759	High Similarity	NPC12402
0.8759	High Similarity	NPC478019
0.8759	High Similarity	NPC259942
0.875	High Similarity	NPC238629
0.875	High Similarity	NPC66593
0.875	High Similarity	NPC167663
0.8741	High Similarity	NPC8745
0.8741	High Similarity	NPC91019
0.8741	High Similarity	NPC106519
0.8733	High Similarity	NPC226656
0.8733	High Similarity	NPC66508
0.8732	High Similarity	NPC26924
0.8723	High Similarity	NPC305060
0.8716	High Similarity	NPC202595
0.8716	High Similarity	NPC205766
0.8714	High Similarity	NPC80035
0.8714	High Similarity	NPC249272
0.8714	High Similarity	NPC290803
0.8714	High Similarity	NPC278375
0.8707	High Similarity	NPC471907
0.8705	High Similarity	NPC225051
0.8705	High Similarity	NPC115458
0.8705	High Similarity	NPC114183
0.8705	High Similarity	NPC48036
0.8705	High Similarity	NPC180261
0.8705	High Similarity	NPC37299
0.8699	High Similarity	NPC271944
0.8699	High Similarity	NPC136878
0.8699	High Similarity	NPC300540
0.8699	High Similarity	NPC110882
0.8699	High Similarity	NPC85393
0.8696	High Similarity	NPC205992
0.869	High Similarity	NPC10764
0.869	High Similarity	NPC79627
0.8686	High Similarity	NPC476119
0.8686	High Similarity	NPC474998
0.8686	High Similarity	NPC109123
0.8681	High Similarity	NPC94076
0.8681	High Similarity	NPC239136
0.8681	High Similarity	NPC182255
0.8681	High Similarity	NPC85310
0.8681	High Similarity	NPC19631
0.8676	High Similarity	NPC72158
0.8676	High Similarity	NPC103356
0.8676	High Similarity	NPC30501
0.8676	High Similarity	NPC23126
0.8676	High Similarity	NPC169250
0.8676	High Similarity	NPC266689
0.8676	High Similarity	NPC105157
0.8676	High Similarity	NPC190043
0.8676	High Similarity	NPC100067
0.8676	High Similarity	NPC162612
0.8676	High Similarity	NPC98254
0.8675	High Similarity	NPC5379
0.8675	High Similarity	NPC474861
0.8675	High Similarity	NPC14561
0.8675	High Similarity	NPC77807
0.8671	High Similarity	NPC315578
0.8667	High Similarity	NPC477454
0.8667	High Similarity	NPC214632
0.8667	High Similarity	NPC103540
0.8658	High Similarity	NPC72958
0.8658	High Similarity	NPC478148
0.8658	High Similarity	NPC46882
0.8658	High Similarity	NPC132990
0.8658	High Similarity	NPC232645
0.8658	High Similarity	NPC149526
0.8658	High Similarity	NPC474417
0.8649	High Similarity	NPC329933
0.8643	High Similarity	NPC270899
0.8643	High Similarity	NPC202225
0.8621	High Similarity	NPC84266
0.8621	High Similarity	NPC471682
0.8621	High Similarity	NPC296752
0.8621	High Similarity	NPC471731
0.8621	High Similarity	NPC159721
0.8618	High Similarity	NPC199463
0.8618	High Similarity	NPC178976
0.8618	High Similarity	NPC37543
0.8613	High Similarity	NPC221777
0.8613	High Similarity	NPC179898
0.8613	High Similarity	NPC473017
0.8613	High Similarity	NPC21305
0.8613	High Similarity	NPC48248
0.8603	High Similarity	NPC160499
0.8603	High Similarity	NPC267846

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 NPC305845 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	956
0.2-0.3	1565
0.3-0.4	2771
0.4-0.5	2030
0.5-0.6	1041
0.6-0.7	339
0.7-0.8	106
0.8-0.85	14
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9627	High Similarity	NPD1509	Clinical (unspecified phase)
0.8819	High Similarity	NPD7390	Discontinued
0.8667	High Similarity	NPD1470	Approved
0.837	Intermediate Similarity	NPD1201	Approved
0.8369	Intermediate Similarity	NPD943	Approved
0.8333	Intermediate Similarity	NPD5408	Approved
0.8333	Intermediate Similarity	NPD5406	Approved
0.8333	Intermediate Similarity	NPD5405	Approved
0.8333	Intermediate Similarity	NPD5404	Approved
0.8217	Intermediate Similarity	NPD6959	Discontinued
0.8165	Intermediate Similarity	NPD6232	Discontinued
0.8138	Intermediate Similarity	NPD1510	Phase 2
0.8125	Intermediate Similarity	NPD7473	Discontinued
0.8125	Intermediate Similarity	NPD1607	Approved
0.8065	Intermediate Similarity	NPD7819	Suspended
0.8014	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2532	Approved
0.8013	Intermediate Similarity	NPD2533	Approved
0.8013	Intermediate Similarity	NPD2534	Approved
0.8013	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4380	Phase 2
0.7986	Intermediate Similarity	NPD1240	Approved
0.7973	Intermediate Similarity	NPD1549	Phase 2
0.7949	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD3226	Approved
0.7794	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1934	Approved
0.7718	Intermediate Similarity	NPD2796	Approved
0.7707	Intermediate Similarity	NPD7411	Suspended
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7688	Intermediate Similarity	NPD7075	Discontinued
0.7622	Intermediate Similarity	NPD1164	Approved
0.761	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2935	Discontinued
0.7578	Intermediate Similarity	NPD3749	Approved
0.7572	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2346	Discontinued
0.7547	Intermediate Similarity	NPD6801	Discontinued
0.7516	Intermediate Similarity	NPD3750	Approved
0.7516	Intermediate Similarity	NPD7768	Phase 2
0.7516	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3882	Suspended
0.7515	Intermediate Similarity	NPD6166	Phase 2
0.7515	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2801	Approved
0.7485	Intermediate Similarity	NPD5494	Approved
0.7484	Intermediate Similarity	NPD1511	Approved
0.7469	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6559	Discontinued
0.7451	Intermediate Similarity	NPD2800	Approved
0.7442	Intermediate Similarity	NPD8150	Discontinued
0.7425	Intermediate Similarity	NPD3818	Discontinued
0.7421	Intermediate Similarity	NPD6599	Discontinued
0.7407	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5711	Approved
0.7394	Intermediate Similarity	NPD5710	Approved
0.7389	Intermediate Similarity	NPD1512	Approved
0.7386	Intermediate Similarity	NPD6534	Approved
0.7386	Intermediate Similarity	NPD6535	Approved
0.7376	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1551	Phase 2
0.7365	Intermediate Similarity	NPD3764	Approved
0.7358	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD230	Phase 1
0.7324	Intermediate Similarity	NPD3019	Approved
0.732	Intermediate Similarity	NPD2344	Approved
0.7292	Intermediate Similarity	NPD9269	Phase 2
0.7285	Intermediate Similarity	NPD6651	Approved
0.7278	Intermediate Similarity	NPD6776	Approved
0.7278	Intermediate Similarity	NPD6778	Approved
0.7278	Intermediate Similarity	NPD6779	Approved
0.7278	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6020	Phase 2
0.7278	Intermediate Similarity	NPD6780	Approved
0.7278	Intermediate Similarity	NPD6782	Approved
0.7278	Intermediate Similarity	NPD6781	Approved
0.7278	Intermediate Similarity	NPD6777	Approved
0.7263	Intermediate Similarity	NPD7699	Phase 2
0.7263	Intermediate Similarity	NPD7700	Phase 2
0.7261	Intermediate Similarity	NPD6799	Approved
0.7255	Intermediate Similarity	NPD6100	Approved
0.7255	Intermediate Similarity	NPD6099	Approved
0.7254	Intermediate Similarity	NPD9268	Approved
0.7243	Intermediate Similarity	NPD8151	Discontinued
0.7235	Intermediate Similarity	NPD7074	Phase 3
0.7222	Intermediate Similarity	NPD37	Approved
0.7203	Intermediate Similarity	NPD2932	Approved
0.7197	Intermediate Similarity	NPD3300	Phase 2
0.7193	Intermediate Similarity	NPD5953	Discontinued
0.719	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2799	Discontinued
0.719	Intermediate Similarity	NPD3748	Approved
0.7179	Intermediate Similarity	NPD4628	Phase 3
0.7179	Intermediate Similarity	NPD7003	Approved
0.7176	Intermediate Similarity	NPD7054	Approved
0.7168	Intermediate Similarity	NPD8313	Approved
0.7168	Intermediate Similarity	NPD8312	Approved
0.7159	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7697	Approved
0.7158	Intermediate Similarity	NPD7435	Discontinued
0.7158	Intermediate Similarity	NPD7698	Approved
0.7158	Intermediate Similarity	NPD7696	Phase 3
0.7153	Intermediate Similarity	NPD4750	Phase 3
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD6213	Phase 3
0.7135	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7472	Approved
0.7135	Intermediate Similarity	NPD6212	Phase 3
0.7134	Intermediate Similarity	NPD3817	Phase 2
0.7134	Intermediate Similarity	NPD5402	Approved
0.7134	Intermediate Similarity	NPD2309	Approved
0.7125	Intermediate Similarity	NPD920	Approved
0.712	Intermediate Similarity	NPD8319	Approved
0.712	Intermediate Similarity	NPD8320	Phase 1
0.712	Intermediate Similarity	NPD7871	Phase 2
0.712	Intermediate Similarity	NPD7870	Phase 2
0.7118	Intermediate Similarity	NPD3751	Discontinued
0.7115	Intermediate Similarity	NPD1243	Approved
0.711	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6797	Phase 2
0.7093	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4966	Approved
0.7091	Intermediate Similarity	NPD4965	Approved
0.7091	Intermediate Similarity	NPD4967	Phase 2
0.7073	Intermediate Similarity	NPD1465	Phase 2
0.707	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7251	Discontinued
0.7042	Intermediate Similarity	NPD9493	Approved
0.7025	Intermediate Similarity	NPD6190	Approved
0.7021	Intermediate Similarity	NPD5951	Approved
0.702	Intermediate Similarity	NPD2313	Discontinued
0.7019	Intermediate Similarity	NPD5403	Approved
0.7011	Intermediate Similarity	NPD7808	Phase 3
0.7011	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2342	Discontinued
0.7006	Intermediate Similarity	NPD6234	Discontinued
0.7005	Intermediate Similarity	NPD7701	Phase 2
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5401	Approved
0.7	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1471	Phase 3
0.6981	Remote Similarity	NPD643	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2798	Approved
0.6977	Remote Similarity	NPD7286	Phase 2
0.6974	Remote Similarity	NPD6663	Approved
0.6959	Remote Similarity	NPD1283	Approved
0.6957	Remote Similarity	NPD6273	Approved
0.6957	Remote Similarity	NPD9266	Approved
0.6957	Remote Similarity	NPD74	Approved
0.6954	Remote Similarity	NPD4625	Phase 3
0.6952	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD9545	Approved
0.6944	Remote Similarity	NPD3091	Approved
0.6941	Remote Similarity	NPD3926	Phase 2
0.6939	Remote Similarity	NPD3972	Approved
0.6933	Remote Similarity	NPD5736	Approved
0.6931	Remote Similarity	NPD7874	Approved
0.6931	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1247	Approved
0.6919	Remote Similarity	NPD6823	Phase 2
0.6918	Remote Similarity	NPD3026	Approved
0.6918	Remote Similarity	NPD3023	Approved
0.6914	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3094	Phase 2
0.6908	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD919	Approved
0.6898	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1651	Approved
0.6897	Remote Similarity	NPD3024	Approved
0.6897	Remote Similarity	NPD3025	Approved
0.6895	Remote Similarity	NPD7801	Approved
0.6884	Remote Similarity	NPD9263	Approved
0.6884	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD9264	Approved
0.6884	Remote Similarity	NPD9267	Approved
0.6882	Remote Similarity	NPD7229	Phase 3
0.6871	Remote Similarity	NPD3092	Approved
0.6871	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3400	Discontinued
0.6855	Remote Similarity	NPD8166	Discontinued
0.6846	Remote Similarity	NPD1876	Approved
0.6826	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7177	Discontinued
0.6821	Remote Similarity	NPD7228	Approved
0.6818	Remote Similarity	NPD5026	Approved
0.6818	Remote Similarity	NPD5028	Approved
0.6818	Remote Similarity	NPD4955	Approved
0.6818	Remote Similarity	NPD4954	Approved
0.6818	Remote Similarity	NPD36	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