NPASS Compound

Structure

NPC163948 OpenBabel07101719252D 27 29 0 0 0 0 0 0 0 0999 V2000 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 -1.0000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 22 1 0 0 0 0 7 27 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 14 1 0 0 0 0 11 23 2 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 18 2 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 24 1 0 0 0 0 18 27 1 0 0 0 0 19 22 1 0 0 0 0 19 25 2 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.16
Volume:	386.258
LogP:	4.036
LogD:	2.796
LogS:	-4.306
# Rotatable Bonds:	2
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.637
Synthetic Accessibility Score:	3.091
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.973
MDCK Permeability:	1.703940324659925e-05
Pgp-inhibitor:	0.752
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.117
20% Bioavailability (F20%):	0.796
30% Bioavailability (F30%):	0.188

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	92.10745239257812%
Volume Distribution (VD):	1.093
Pgp-substrate:	5.550143241882324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.601
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.724
CYP2C19-substrate:	0.831
CYP2C9-inhibitor:	0.758
CYP2C9-substrate:	0.769
CYP2D6-inhibitor:	0.189
CYP2D6-substrate:	0.239
CYP3A4-inhibitor:	0.458
CYP3A4-substrate:	0.846

ADMET: Excretion

Clearance (CL):	1.575
Half-life (T1/2):	0.203

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.548
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.156
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.19
Skin Sensitization:	0.366
Carcinogencity:	0.067
Eye Corrosion:	0.003
Eye Irritation:	0.778
Respiratory Toxicity:	0.744

Download Data

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

Natural Product: NPC163948

Natural Product ID:	NPC163948
*Common Name:**	Garveatin C
IUPAC Name:	7-acetyl-9-hydroxy-8-methoxy-2,2,4,4,6-pentamethylanthracene-1,3-dione
Synonyms:	Garveatin C
Standard InCHIKey:	BRECKZGJFRHNPM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H24O5/c1-10-8-12-9-13-16(19(25)22(5,6)20(26)21(13,3)4)17(24)15(12)18(27-7)14(10)11(2)23/h8-9,24H,1-7H3
SMILES:	COc1c(C(=O)C)c(C)cc2c1c(O)c1c(c2)C(C)(C)C(=O)C(C1=O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505049
PubChem CID:	356405
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO2240	Garveia annulata	Species	Bougainvilliidae	Eukaryota	n.a.	Northeastern Pacific	n.a.	PMID[17067170]
NPO2240	Garveia annulata	Species	Bougainvilliidae	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
Ki	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	Ki	=	1200.0	nM	PMID[521223]

☑ 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 NPC163948 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	378
0.1-0.2	1629
0.2-0.3	3642
0.3-0.4	9744
0.4-0.5	9286
0.5-0.6	4460
0.6-0.7	6894
0.7-0.8	5801
0.8-0.85	770
0.85-0.9	91
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.906	High Similarity	NPC474360
0.9034	High Similarity	NPC34802
0.8912	High Similarity	NPC329933
0.8889	High Similarity	NPC84266
0.8849	High Similarity	NPC114183
0.8819	High Similarity	NPC69755
0.8819	High Similarity	NPC182255
0.8819	High Similarity	NPC94076
0.8792	High Similarity	NPC474417
0.8792	High Similarity	NPC149526
0.8786	High Similarity	NPC12070
0.8786	High Similarity	NPC270899
0.8784	High Similarity	NPC97029
0.8784	High Similarity	NPC158338
0.8784	High Similarity	NPC65589
0.8784	High Similarity	NPC288036
0.8784	High Similarity	NPC100985
0.8784	High Similarity	NPC97028
0.8776	High Similarity	NPC245584
0.8776	High Similarity	NPC289042
0.8776	High Similarity	NPC118027
0.8776	High Similarity	NPC56433
0.8776	High Similarity	NPC190648
0.8776	High Similarity	NPC126767
0.8776	High Similarity	NPC312929
0.8767	High Similarity	NPC478019
0.8759	High Similarity	NPC53016
0.8725	High Similarity	NPC470568
0.8723	High Similarity	NPC249272
0.8716	High Similarity	NPC7025
0.8716	High Similarity	NPC27221
0.8716	High Similarity	NPC256672
0.8707	High Similarity	NPC143685
0.8684	High Similarity	NPC221992
0.8675	High Similarity	NPC329844
0.8675	High Similarity	NPC208806
0.8667	High Similarity	NPC232645
0.8667	High Similarity	NPC478148
0.8667	High Similarity	NPC470569
0.8667	High Similarity	NPC72958
0.8649	High Similarity	NPC478018
0.8649	High Similarity	NPC22005
0.8649	High Similarity	NPC7943
0.8649	High Similarity	NPC123202
0.863	High Similarity	NPC66593
0.8618	High Similarity	NPC226656
0.8618	High Similarity	NPC66508
0.8611	High Similarity	NPC1268
0.8609	High Similarity	NPC40356
0.8609	High Similarity	NPC154683
0.8609	High Similarity	NPC87708
0.8601	High Similarity	NPC53001
0.86	High Similarity	NPC255641
0.86	High Similarity	NPC294646
0.86	High Similarity	NPC290954
0.86	High Similarity	NPC147735
0.8581	High Similarity	NPC225173
0.8581	High Similarity	NPC300540
0.8581	High Similarity	NPC163846
0.8571	High Similarity	NPC19896
0.8571	High Similarity	NPC260152
0.8553	High Similarity	NPC214632
0.8553	High Similarity	NPC169990
0.8553	High Similarity	NPC210942
0.8543	High Similarity	NPC145830
0.8542	High Similarity	NPC87723
0.8523	High Similarity	NPC125801
0.8523	High Similarity	NPC52692
0.8516	High Similarity	NPC476506
0.8514	High Similarity	NPC12402
0.8514	High Similarity	NPC34482
0.8506	High Similarity	NPC272196
0.8506	High Similarity	NPC67197
0.8506	High Similarity	NPC263483
0.8503	High Similarity	NPC167663
0.8493	Intermediate Similarity	NPC11056
0.8493	Intermediate Similarity	NPC124365
0.8487	Intermediate Similarity	NPC164912
0.8478	Intermediate Similarity	NPC160499
0.8477	Intermediate Similarity	NPC325983
0.8456	Intermediate Similarity	NPC60389
0.8456	Intermediate Similarity	NPC470570
0.8456	Intermediate Similarity	NPC211565
0.8452	Intermediate Similarity	NPC324736
0.8446	Intermediate Similarity	NPC193703
0.8446	Intermediate Similarity	NPC48762
0.8446	Intermediate Similarity	NPC21599
0.8446	Intermediate Similarity	NPC189650
0.844	Intermediate Similarity	NPC164295
0.8435	Intermediate Similarity	NPC126534
0.8435	Intermediate Similarity	NPC40118
0.8435	Intermediate Similarity	NPC49108
0.8435	Intermediate Similarity	NPC232021
0.8435	Intermediate Similarity	NPC201297
0.8431	Intermediate Similarity	NPC179170
0.8431	Intermediate Similarity	NPC107109
0.8431	Intermediate Similarity	NPC93552
0.8429	Intermediate Similarity	NPC57552
0.8425	Intermediate Similarity	NPC472366
0.8425	Intermediate Similarity	NPC109232
0.8425	Intermediate Similarity	NPC168471
0.8421	Intermediate Similarity	NPC258249
0.8421	Intermediate Similarity	NPC118427
0.8421	Intermediate Similarity	NPC133856
0.8411	Intermediate Similarity	NPC233267
0.8411	Intermediate Similarity	NPC291049
0.8403	Intermediate Similarity	NPC141934
0.8403	Intermediate Similarity	NPC191976
0.8403	Intermediate Similarity	NPC471670
0.8397	Intermediate Similarity	NPC472052
0.8397	Intermediate Similarity	NPC186325
0.8397	Intermediate Similarity	NPC472060
0.8397	Intermediate Similarity	NPC470342
0.8392	Intermediate Similarity	NPC274876
0.8389	Intermediate Similarity	NPC49282
0.8389	Intermediate Similarity	NPC476055
0.8387	Intermediate Similarity	NPC199463
0.8387	Intermediate Similarity	NPC474637
0.8387	Intermediate Similarity	NPC37543
0.8387	Intermediate Similarity	NPC201127
0.8378	Intermediate Similarity	NPC310340
0.8378	Intermediate Similarity	NPC297600
0.8377	Intermediate Similarity	NPC3898
0.8367	Intermediate Similarity	NPC265178
0.8367	Intermediate Similarity	NPC149780
0.8366	Intermediate Similarity	NPC175978
0.8366	Intermediate Similarity	NPC217447
0.8357	Intermediate Similarity	NPC48248
0.8356	Intermediate Similarity	NPC470407
0.8356	Intermediate Similarity	NPC243528
0.8356	Intermediate Similarity	NPC251681
0.8355	Intermediate Similarity	NPC202595
0.8355	Intermediate Similarity	NPC205766
0.8354	Intermediate Similarity	NPC476505
0.8344	Intermediate Similarity	NPC172329
0.8344	Intermediate Similarity	NPC472261
0.8344	Intermediate Similarity	NPC105415
0.8344	Intermediate Similarity	NPC472841
0.8344	Intermediate Similarity	NPC189552
0.8344	Intermediate Similarity	NPC2569
0.8344	Intermediate Similarity	NPC273467
0.8333	Intermediate Similarity	NPC281398
0.8333	Intermediate Similarity	NPC103842
0.8333	Intermediate Similarity	NPC228654
0.8333	Intermediate Similarity	NPC177650
0.8323	Intermediate Similarity	NPC14561
0.8323	Intermediate Similarity	NPC279605
0.8323	Intermediate Similarity	NPC5379
0.8323	Intermediate Similarity	NPC180924
0.8323	Intermediate Similarity	NPC4547
0.8323	Intermediate Similarity	NPC146211
0.8323	Intermediate Similarity	NPC77807
0.8322	Intermediate Similarity	NPC309169
0.8322	Intermediate Similarity	NPC196941
0.8322	Intermediate Similarity	NPC267205
0.8322	Intermediate Similarity	NPC470406
0.8322	Intermediate Similarity	NPC11700
0.8311	Intermediate Similarity	NPC250755
0.8311	Intermediate Similarity	NPC193555
0.831	Intermediate Similarity	NPC239134
0.8301	Intermediate Similarity	NPC305965
0.8299	Intermediate Similarity	NPC283429
0.8299	Intermediate Similarity	NPC315578
0.8299	Intermediate Similarity	NPC165172
0.8298	Intermediate Similarity	NPC276238
0.8298	Intermediate Similarity	NPC206028
0.8289	Intermediate Similarity	NPC473978
0.8289	Intermediate Similarity	NPC80370
0.8289	Intermediate Similarity	NPC65775
0.8289	Intermediate Similarity	NPC10027
0.8288	Intermediate Similarity	NPC23870
0.8288	Intermediate Similarity	NPC4214
0.828	Intermediate Similarity	NPC312993
0.828	Intermediate Similarity	NPC470810
0.8278	Intermediate Similarity	NPC10990
0.8278	Intermediate Similarity	NPC300988
0.8278	Intermediate Similarity	NPC71055
0.8276	Intermediate Similarity	NPC472308
0.8276	Intermediate Similarity	NPC13575
0.8276	Intermediate Similarity	NPC131039
0.8276	Intermediate Similarity	NPC156092
0.8276	Intermediate Similarity	NPC474311
0.8269	Intermediate Similarity	NPC212967
0.8269	Intermediate Similarity	NPC164110
0.8269	Intermediate Similarity	NPC96342
0.8269	Intermediate Similarity	NPC246647
0.8269	Intermediate Similarity	NPC178976
0.8267	Intermediate Similarity	NPC470674
0.8267	Intermediate Similarity	NPC117716
0.8267	Intermediate Similarity	NPC470673
0.8264	Intermediate Similarity	NPC1249
0.8258	Intermediate Similarity	NPC149618
0.8258	Intermediate Similarity	NPC89625
0.8255	Intermediate Similarity	NPC1534
0.8252	Intermediate Similarity	NPC183103
0.8247	Intermediate Similarity	NPC113608
0.8247	Intermediate Similarity	NPC470338
0.8247	Intermediate Similarity	NPC470337
0.8247	Intermediate Similarity	NPC268992
0.8247	Intermediate Similarity	NPC474993

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 NPC163948 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	992
0.2-0.3	1435
0.3-0.4	2618
0.4-0.5	2113
0.5-0.6	1113
0.6-0.7	411
0.7-0.8	110
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8228	Intermediate Similarity	NPD6959	Discontinued
0.8176	Intermediate Similarity	NPD6232	Discontinued
0.817	Intermediate Similarity	NPD3226	Approved
0.8163	Intermediate Similarity	NPD2346	Discontinued
0.8151	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7473	Discontinued
0.8095	Intermediate Similarity	NPD2935	Discontinued
0.8079	Intermediate Similarity	NPD7390	Discontinued
0.8026	Intermediate Similarity	NPD2532	Approved
0.8026	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD2534	Approved
0.8026	Intermediate Similarity	NPD2533	Approved
0.8025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD7003	Approved
0.7962	Intermediate Similarity	NPD7819	Suspended
0.7908	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1510	Phase 2
0.7891	Intermediate Similarity	NPD6651	Approved
0.7877	Intermediate Similarity	NPD1240	Approved
0.7867	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1201	Approved
0.7852	Intermediate Similarity	NPD5408	Approved
0.7852	Intermediate Similarity	NPD5405	Approved
0.7852	Intermediate Similarity	NPD5406	Approved
0.7852	Intermediate Similarity	NPD6099	Approved
0.7852	Intermediate Similarity	NPD5404	Approved
0.7852	Intermediate Similarity	NPD6100	Approved
0.7848	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD7411	Suspended
0.7821	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2800	Approved
0.7801	Intermediate Similarity	NPD3972	Approved
0.7762	Intermediate Similarity	NPD1470	Approved
0.7744	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD2798	Approved
0.7707	Intermediate Similarity	NPD7458	Discontinued
0.7697	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2344	Approved
0.7682	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4380	Phase 2
0.7643	Intermediate Similarity	NPD1651	Approved
0.7632	Intermediate Similarity	NPD1549	Phase 2
0.7619	Intermediate Similarity	NPD2313	Discontinued
0.7619	Intermediate Similarity	NPD3268	Approved
0.7569	Intermediate Similarity	NPD1283	Approved
0.7566	Intermediate Similarity	NPD1471	Phase 3
0.7564	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1934	Approved
0.755	Intermediate Similarity	NPD2799	Discontinued
0.7547	Intermediate Similarity	NPD6599	Discontinued
0.7532	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7768	Phase 2
0.7516	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD1511	Approved
0.7485	Intermediate Similarity	NPD3749	Approved
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.7484	Intermediate Similarity	NPD2309	Approved
0.7452	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4625	Phase 3
0.7419	Intermediate Similarity	NPD3750	Approved
0.741	Intermediate Similarity	NPD5710	Approved
0.741	Intermediate Similarity	NPD5711	Approved
0.7407	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1512	Approved
0.7397	Intermediate Similarity	NPD1203	Approved
0.7386	Intermediate Similarity	NPD1551	Phase 2
0.7361	Intermediate Similarity	NPD1281	Approved
0.7343	Intermediate Similarity	NPD4626	Approved
0.7321	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6166	Phase 2
0.7321	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4308	Phase 3
0.7317	Intermediate Similarity	NPD3882	Suspended
0.7308	Intermediate Similarity	NPD4628	Phase 3
0.7296	Intermediate Similarity	NPD6273	Approved
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2797	Approved
0.7279	Intermediate Similarity	NPD3267	Approved
0.7279	Intermediate Similarity	NPD3266	Approved
0.7273	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD411	Approved
0.7267	Intermediate Similarity	NPD6559	Discontinued
0.7248	Intermediate Similarity	NPD6832	Phase 2
0.7241	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6801	Discontinued
0.7235	Intermediate Similarity	NPD7177	Discontinued
0.7222	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3019	Approved
0.7211	Intermediate Similarity	NPD1876	Approved
0.7208	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7008	Discontinued
0.72	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD9717	Approved
0.719	Intermediate Similarity	NPD4097	Suspended
0.7186	Intermediate Similarity	NPD5494	Approved
0.7184	Intermediate Similarity	NPD8313	Approved
0.7184	Intermediate Similarity	NPD8312	Approved
0.7183	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD9493	Approved
0.7175	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2979	Phase 3
0.7171	Intermediate Similarity	NPD943	Approved
0.717	Intermediate Similarity	NPD6799	Approved
0.7169	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5951	Approved
0.7162	Intermediate Similarity	NPD1164	Approved
0.7152	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1243	Approved
0.7124	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2932	Approved
0.7097	Intermediate Similarity	NPD3748	Approved
0.7093	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5890	Approved
0.7073	Intermediate Similarity	NPD5889	Approved
0.7062	Intermediate Similarity	NPD8150	Discontinued
0.7059	Intermediate Similarity	NPD4307	Phase 2
0.7052	Intermediate Similarity	NPD7074	Phase 3
0.7051	Intermediate Similarity	NPD2438	Suspended
0.7039	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3818	Discontinued
0.7034	Intermediate Similarity	NPD5691	Approved
0.7029	Intermediate Similarity	NPD2342	Discontinued
0.7029	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD447	Suspended
0.7012	Intermediate Similarity	NPD6585	Discontinued
0.7011	Intermediate Similarity	NPD6778	Approved
0.7011	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6782	Approved
0.7011	Intermediate Similarity	NPD6780	Approved
0.7011	Intermediate Similarity	NPD6776	Approved
0.7011	Intermediate Similarity	NPD6777	Approved
0.7011	Intermediate Similarity	NPD6779	Approved
0.7011	Intermediate Similarity	NPD6781	Approved
0.7	Intermediate Similarity	NPD3300	Phase 2
0.6994	Remote Similarity	NPD7054	Approved
0.6993	Remote Similarity	NPD8032	Phase 2
0.6988	Remote Similarity	NPD1465	Phase 2
0.6959	Remote Similarity	NPD1608	Approved
0.6959	Remote Similarity	NPD3926	Phase 2
0.6954	Remote Similarity	NPD7472	Approved
0.6948	Remote Similarity	NPD4060	Phase 1
0.6946	Remote Similarity	NPD5402	Approved
0.6946	Remote Similarity	NPD2296	Approved
0.6946	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2531	Phase 2
0.6941	Remote Similarity	NPD1247	Approved
0.6937	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD920	Approved
0.6933	Remote Similarity	NPD5403	Approved
0.6933	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3764	Approved
0.6928	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD37	Approved
0.6928	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5953	Discontinued
0.6914	Remote Similarity	NPD6797	Phase 2
0.6913	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4749	Approved
0.6903	Remote Similarity	NPD1933	Approved
0.6901	Remote Similarity	NPD7635	Approved
0.6901	Remote Similarity	NPD7229	Phase 3
0.6898	Remote Similarity	NPD7696	Phase 3
0.6898	Remote Similarity	NPD7435	Discontinued
0.6898	Remote Similarity	NPD7698	Approved
0.6898	Remote Similarity	NPD7697	Approved
0.6895	Remote Similarity	NPD8151	Discontinued
0.6894	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1611	Approved
0.6886	Remote Similarity	NPD5761	Phase 2
0.6886	Remote Similarity	NPD5760	Phase 2
0.6879	Remote Similarity	NPD7033	Discontinued
0.6879	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8166	Discontinued
0.6875	Remote Similarity	NPD7251	Discontinued
0.6871	Remote Similarity	NPD1778	Approved
0.6871	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6212	Phase 3
0.6868	Remote Similarity	NPD6213	Phase 3
0.6867	Remote Similarity	NPD3225	Approved
0.6867	Remote Similarity	NPD6696	Suspended
0.6862	Remote Similarity	NPD7871	Phase 2
0.6862	Remote Similarity	NPD7870	Phase 2
0.6852	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3751	Discontinued
0.6836	Remote Similarity	NPD7808	Phase 3
0.6835	Remote Similarity	NPD4477	Approved
0.6835	Remote Similarity	NPD4476	Approved
0.6831	Remote Similarity	NPD6535	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