NPASS Compound

Structure

CID51824 OpenBabel06191715392D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.2588 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 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 1.0000 0.0000 C 0 0 1 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 -0.0000 1.0000 0.0000 C 0 0 2 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 0.0000 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 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 2.5981 2.5000 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 -0.7934 0.6088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 23 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 6 1 0 0 0 0 4 9 2 0 0 0 0 5 10 1 0 0 0 0 6 23 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 5 1 6 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 16 1 6 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 19 2 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.15
Volume:	330.904
LogP:	3.168
LogD:	3.501
LogS:	-4.222
# Rotatable Bonds:	7
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.82
Synthetic Accessibility Score:	2.058
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.851
MDCK Permeability:	1.7118441974162124e-05
Pgp-inhibitor:	0.064
Pgp-substrate:	0.827
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.565
30% Bioavailability (F30%):	0.058

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	97.4001693725586%
Volume Distribution (VD):	0.76
Pgp-substrate:	2.521360397338867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.947
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.852
CYP2C19-substrate:	0.675
CYP2C9-inhibitor:	0.62
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.812
CYP2D6-substrate:	0.944
CYP3A4-inhibitor:	0.738
CYP3A4-substrate:	0.564

ADMET: Excretion

Clearance (CL):	12.333
Half-life (T1/2):	0.866

ADMET: Toxicity

hERG Blockers:	0.102
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.44
AMES Toxicity:	0.125
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.286
Skin Sensitization:	0.938
Carcinogencity:	0.073
Eye Corrosion:	0.056
Eye Irritation:	0.926
Respiratory Toxicity:	0.596

Download Data

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

Natural Product: NPC51824

Natural Product ID:	NPC51824
*Common Name:**	Altersolanol L
IUPAC Name:	(2R,3R,4R,4aS,9aS,10R)-2,3,4,8,10-pentahydroxy-6-methoxy-3-methyl-1,2,4,4a,9a,10-hexahydroanthracen-9-one
Synonyms:	Altersolanol L
Standard InCHIKey:	NDGIDBHYSCKXJM-CBDPYCFPSA-N
Standard InCHI:	InChI=1S/C16H20O7/c1-16(22)10(18)5-8-12(15(16)21)14(20)7-3-6(23-2)4-9(17)11(7)13(8)19/h3-4,8,10,12,14-15,17-18,20-22H,5H2,1-2H3/t8-,10+,12-,14-,15+,16+/m0/s1
SMILES:	COc1cc2[C@H](O)[C@@H]3[C@@H](C(=O)c2c(c1)O)C[C@H]([C@@]([C@@H]3O)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL551302
PubChem CID:	42639666
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
NPO17255	Chondrosia corticata	Species	Chondrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568783]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18494522]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271717]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	Mentha pulegium	n.a.	n.a.	PMID[19271717]
NPO22865	Neopetrosia proxima	Species	Petrosiidae	Eukaryota	n.a.	Caribbean sea	n.a.	PMID[20727745]
NPO22865	Neopetrosia proxima	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21341726]
NPO17255	Chondrosia corticata	Species	Chondrillidae	Eukaryota	n.a.	reef slopes on the south side of Cocos Lagoon, Guam	n.a.	PMID[21550239]
NPO18542	Salvia sahendica	Species	Lamiaceae	Eukaryota	n.a.	collected from the plants natural habitat in Tabriz, Northwestern Iran, at an altitude of 1400 m	n.a.	PMID[21775156]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276679]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23664494]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	isolated from fresh Juncus acutus	Lake Wadi el Natrun, Egypt	2012-NOV	PMID[25010124]
NPO33215	Stemphylium sp. 33231	Species	Pleosporaceae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25136754]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25265160]
NPO18279	Paraconiothyrium brasiliense	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25760674]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841051]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30794407]
NPO18194	Primula modesta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18194	Primula modesta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15888	Streptogonopus phipsoni	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19726	Limnatis nilotica	Species	Hirudinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18944	Vernonia filigera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19382	Corallina elongata	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18194	Primula modesta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18542	Salvia sahendica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14894	Udotea conglutinata	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19101	Deutzia gracilis	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22865	Neopetrosia proxima	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19321	0tholaena californica	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18279	Paraconiothyrium brasiliense	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18687	Pterocarpus gracilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18080	Peltophorum ferrugineum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17255	Chondrosia corticata	Species	Chondrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13444	Centaurea ptosimopappoides	Species	Asteraceae	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	7
MIC	7
Others	1

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	2
Organism	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	Activity	=	51.4	%	PMID[566117]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	100000.0	nM	PMID[566118]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[566118]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[566118]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[566119]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[566118]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[566119]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	>	10000.0	nM	PMID[566119]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	10000.0	nM	PMID[566119]
NPT1238	Organism	Staphylococcus	Staphylococcus	MIC	>	10000.0	nM	PMID[566119]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	10000.0	nM	PMID[566119]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	10000.0	nM	PMID[566119]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	>	10000.0	nM	PMID[566119]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	10000.0	nM	PMID[566119]
NPT2	Others	Unspecified		IC50	>	100000	nM	PMID[22276679]

☑ 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 NPC51824 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	382
0.1-0.2	1383
0.2-0.3	3020
0.3-0.4	7108
0.4-0.5	10808
0.5-0.6	4597
0.6-0.7	4894
0.7-0.8	6840
0.8-0.85	2857
0.85-0.9	756
0.9-0.95	38
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470337
1.0	High Similarity	NPC113608
1.0	High Similarity	NPC470338
1.0	High Similarity	NPC268992
0.9864	High Similarity	NPC68727
0.9863	High Similarity	NPC180944
0.9728	High Similarity	NPC470340
0.9726	High Similarity	NPC225854
0.9667	High Similarity	NPC470339
0.9603	High Similarity	NPC472055
0.9474	High Similarity	NPC161947
0.9474	High Similarity	NPC155302
0.9412	High Similarity	NPC87431
0.9404	High Similarity	NPC164427
0.94	High Similarity	NPC155686
0.9396	High Similarity	NPC46882
0.9396	High Similarity	NPC132990
0.9267	High Similarity	NPC470569
0.9247	High Similarity	NPC3732
0.9231	High Similarity	NPC472049
0.9221	High Similarity	NPC470810
0.9211	High Similarity	NPC175192
0.9205	High Similarity	NPC167903
0.92	High Similarity	NPC470568
0.92	High Similarity	NPC147735
0.9133	High Similarity	NPC329933
0.9128	High Similarity	NPC34802
0.9091	High Similarity	NPC179732
0.9073	High Similarity	NPC290954
0.9073	High Similarity	NPC255641
0.9054	High Similarity	NPC19896
0.9054	High Similarity	NPC95751
0.9032	High Similarity	NPC329091
0.9032	High Similarity	NPC85121
0.9026	High Similarity	NPC472050
0.9026	High Similarity	NPC24640
0.902	High Similarity	NPC107109
0.902	High Similarity	NPC93552
0.9013	High Similarity	NPC46564
0.9013	High Similarity	NPC474417
0.9013	High Similarity	NPC207346
0.9013	High Similarity	NPC149526
0.9013	High Similarity	NPC478148
0.9007	High Similarity	NPC270160
0.9007	High Similarity	NPC237440
0.9	High Similarity	NPC312929
0.9	High Similarity	NPC126767
0.9	High Similarity	NPC190648
0.9	High Similarity	NPC118027
0.9	High Similarity	NPC51070
0.9	High Similarity	NPC289042
0.9	High Similarity	NPC222298
0.9	High Similarity	NPC56433
0.9	High Similarity	NPC245584
0.8994	High Similarity	NPC470341
0.8994	High Similarity	NPC324522
0.8994	High Similarity	NPC105414
0.8994	High Similarity	NPC234497
0.8994	High Similarity	NPC472058
0.8981	High Similarity	NPC478229
0.8981	High Similarity	NPC472059
0.8981	High Similarity	NPC215612
0.8981	High Similarity	NPC473961
0.8974	High Similarity	NPC321399
0.8968	High Similarity	NPC37543
0.8968	High Similarity	NPC246466
0.8968	High Similarity	NPC199463
0.8961	High Similarity	NPC67396
0.8954	High Similarity	NPC323626
0.8954	High Similarity	NPC474843
0.8954	High Similarity	NPC154683
0.8954	High Similarity	NPC87708
0.8954	High Similarity	NPC324233
0.8954	High Similarity	NPC40356
0.8947	High Similarity	NPC294646
0.8947	High Similarity	NPC85131
0.8947	High Similarity	NPC202595
0.8933	High Similarity	NPC316769
0.8931	High Similarity	NPC469394
0.8924	High Similarity	NPC472053
0.8924	High Similarity	NPC476295
0.8924	High Similarity	NPC100849
0.8919	High Similarity	NPC232021
0.8919	High Similarity	NPC40118
0.8919	High Similarity	NPC49108
0.8919	High Similarity	NPC126534
0.8917	High Similarity	NPC117985
0.891	High Similarity	NPC477410
0.891	High Similarity	NPC324736
0.891	High Similarity	NPC210459
0.891	High Similarity	NPC472617
0.8903	High Similarity	NPC5379
0.8903	High Similarity	NPC478223
0.8903	High Similarity	NPC77807
0.8903	High Similarity	NPC14561
0.8896	High Similarity	NPC74924
0.8889	High Similarity	NPC470675
0.8889	High Similarity	NPC473131
0.8889	High Similarity	NPC232645
0.8889	High Similarity	NPC70016
0.8889	High Similarity	NPC215921
0.8889	High Similarity	NPC72958
0.8875	High Similarity	NPC6588
0.8875	High Similarity	NPC477154
0.8875	High Similarity	NPC474024
0.8875	High Similarity	NPC117854
0.8875	High Similarity	NPC225419
0.8875	High Similarity	NPC472622
0.8874	High Similarity	NPC470670
0.8874	High Similarity	NPC473133
0.8874	High Similarity	NPC47388
0.8868	High Similarity	NPC472057
0.8868	High Similarity	NPC25361
0.8868	High Similarity	NPC472051
0.8867	High Similarity	NPC478019
0.8867	High Similarity	NPC34482
0.8861	High Similarity	NPC472964
0.8861	High Similarity	NPC211107
0.8859	High Similarity	NPC51106
0.8859	High Similarity	NPC472006
0.8859	High Similarity	NPC84266
0.8854	High Similarity	NPC472618
0.8854	High Similarity	NPC84571
0.8854	High Similarity	NPC36217
0.8854	High Similarity	NPC472902
0.8851	High Similarity	NPC265178
0.8846	High Similarity	NPC272196
0.8846	High Similarity	NPC178976
0.8839	High Similarity	NPC472048
0.8839	High Similarity	NPC16082
0.8839	High Similarity	NPC321779
0.8839	High Similarity	NPC82592
0.8831	High Similarity	NPC253904
0.8831	High Similarity	NPC312338
0.8831	High Similarity	NPC149889
0.8831	High Similarity	NPC106976
0.8831	High Similarity	NPC321363
0.8827	High Similarity	NPC472620
0.8824	High Similarity	NPC179178
0.8824	High Similarity	NPC469670
0.8824	High Similarity	NPC469619
0.882	High Similarity	NPC300307
0.882	High Similarity	NPC188079
0.8816	High Similarity	NPC172329
0.8816	High Similarity	NPC166036
0.8816	High Similarity	NPC203077
0.8816	High Similarity	NPC2569
0.8816	High Similarity	NPC476058
0.8816	High Similarity	NPC238279
0.8812	High Similarity	NPC43319
0.8812	High Similarity	NPC20237
0.8812	High Similarity	NPC170245
0.8812	High Similarity	NPC472621
0.8808	High Similarity	NPC24136
0.8808	High Similarity	NPC470570
0.8808	High Similarity	NPC107625
0.8808	High Similarity	NPC290133
0.8808	High Similarity	NPC187282
0.8805	High Similarity	NPC197168
0.8805	High Similarity	NPC475985
0.8805	High Similarity	NPC474240
0.8805	High Similarity	NPC7483
0.8805	High Similarity	NPC186686
0.8805	High Similarity	NPC249181
0.88	High Similarity	NPC86373
0.88	High Similarity	NPC280404
0.88	High Similarity	NPC476178
0.88	High Similarity	NPC210425
0.88	High Similarity	NPC244691
0.88	High Similarity	NPC48762
0.88	High Similarity	NPC277426
0.88	High Similarity	NPC117836
0.88	High Similarity	NPC475201
0.88	High Similarity	NPC51887
0.88	High Similarity	NPC475705
0.8797	High Similarity	NPC18380
0.8797	High Similarity	NPC61010
0.8797	High Similarity	NPC137232
0.8797	High Similarity	NPC316457
0.8797	High Similarity	NPC474186
0.8797	High Similarity	NPC311740
0.8797	High Similarity	NPC478222
0.8792	High Similarity	NPC474961
0.8792	High Similarity	NPC470087
0.8792	High Similarity	NPC182255
0.8792	High Similarity	NPC321980
0.8792	High Similarity	NPC94076
0.879	High Similarity	NPC476242
0.879	High Similarity	NPC186113
0.879	High Similarity	NPC473990
0.8784	High Similarity	NPC201541
0.8784	High Similarity	NPC469523
0.8782	High Similarity	NPC208152
0.8782	High Similarity	NPC474167
0.8782	High Similarity	NPC78492
0.8782	High Similarity	NPC470762
0.8782	High Similarity	NPC142339
0.8774	High Similarity	NPC298692
0.8774	High Similarity	NPC210942
0.8774	High Similarity	NPC169990

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 NPC51824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	872
0.2-0.3	1681
0.3-0.4	2624
0.4-0.5	1941
0.5-0.6	1036
0.6-0.7	468
0.7-0.8	160
0.8-0.85	34
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8774	High Similarity	NPD2393	Clinical (unspecified phase)
0.8696	High Similarity	NPD7473	Discontinued
0.8625	High Similarity	NPD6232	Discontinued
0.859	High Similarity	NPD1934	Approved
0.8581	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD6959	Discontinued
0.8497	Intermediate Similarity	NPD2532	Approved
0.8497	Intermediate Similarity	NPD2533	Approved
0.8497	Intermediate Similarity	NPD2534	Approved
0.8467	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD2801	Approved
0.8405	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD6166	Phase 2
0.8389	Intermediate Similarity	NPD1510	Phase 2
0.8377	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1511	Approved
0.8302	Intermediate Similarity	NPD7819	Suspended
0.8278	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1607	Approved
0.8243	Intermediate Similarity	NPD1240	Approved
0.8224	Intermediate Similarity	NPD1549	Phase 2
0.8205	Intermediate Similarity	NPD1512	Approved
0.8199	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD3882	Suspended
0.8193	Intermediate Similarity	NPD3818	Discontinued
0.816	Intermediate Similarity	NPD5494	Approved
0.8148	Intermediate Similarity	NPD7075	Discontinued
0.8148	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5844	Phase 1
0.8141	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD37	Approved
0.8095	Intermediate Similarity	NPD7074	Phase 3
0.8092	Intermediate Similarity	NPD2796	Approved
0.8077	Intermediate Similarity	NPD7390	Discontinued
0.8075	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7054	Approved
0.8025	Intermediate Similarity	NPD3817	Phase 2
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6234	Discontinued
0.7988	Intermediate Similarity	NPD7472	Approved
0.7975	Intermediate Similarity	NPD4967	Phase 2
0.7975	Intermediate Similarity	NPD4965	Approved
0.7975	Intermediate Similarity	NPD4966	Approved
0.7974	Intermediate Similarity	NPD6100	Approved
0.7974	Intermediate Similarity	NPD6099	Approved
0.795	Intermediate Similarity	NPD7411	Suspended
0.7941	Intermediate Similarity	NPD6797	Phase 2
0.7935	Intermediate Similarity	NPD2800	Approved
0.7929	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3749	Approved
0.7895	Intermediate Similarity	NPD7251	Discontinued
0.7895	Intermediate Similarity	NPD6651	Approved
0.7895	Intermediate Similarity	NPD6559	Discontinued
0.7888	Intermediate Similarity	NPD6599	Discontinued
0.7881	Intermediate Similarity	NPD943	Approved
0.7857	Intermediate Similarity	NPD2935	Discontinued
0.7849	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7808	Phase 3
0.7848	Intermediate Similarity	NPD6799	Approved
0.7844	Intermediate Similarity	NPD5710	Approved
0.7844	Intermediate Similarity	NPD5711	Approved
0.7836	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3226	Approved
0.7805	Intermediate Similarity	NPD5402	Approved
0.7799	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD8150	Discontinued
0.7771	Intermediate Similarity	NPD3750	Approved
0.7771	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7228	Approved
0.7765	Intermediate Similarity	NPD3751	Discontinued
0.7758	Intermediate Similarity	NPD7768	Phase 2
0.7751	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1465	Phase 2
0.7738	Intermediate Similarity	NPD3787	Discontinued
0.7712	Intermediate Similarity	NPD230	Phase 1
0.7701	Intermediate Similarity	NPD8313	Approved
0.7701	Intermediate Similarity	NPD8312	Approved
0.7692	Intermediate Similarity	NPD6782	Approved
0.7692	Intermediate Similarity	NPD6778	Approved
0.7692	Intermediate Similarity	NPD6779	Approved
0.7692	Intermediate Similarity	NPD6776	Approved
0.7692	Intermediate Similarity	NPD6780	Approved
0.7692	Intermediate Similarity	NPD6777	Approved
0.7692	Intermediate Similarity	NPD6781	Approved
0.7684	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7651	Intermediate Similarity	NPD1470	Approved
0.7647	Intermediate Similarity	NPD8151	Discontinued
0.7619	Intermediate Similarity	NPD1201	Approved
0.7614	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5403	Approved
0.758	Intermediate Similarity	NPD2346	Discontinued
0.7574	Intermediate Similarity	NPD7199	Phase 2
0.7571	Intermediate Similarity	NPD8434	Phase 2
0.7568	Intermediate Similarity	NPD7435	Discontinued
0.7566	Intermediate Similarity	NPD3027	Phase 3
0.7543	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD5761	Phase 2
0.753	Intermediate Similarity	NPD5760	Phase 2
0.7516	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7696	Phase 3
0.7473	Intermediate Similarity	NPD7698	Approved
0.7473	Intermediate Similarity	NPD7697	Approved
0.7469	Intermediate Similarity	NPD5401	Approved
0.7469	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3300	Phase 2
0.7452	Intermediate Similarity	NPD2799	Discontinued
0.7452	Intermediate Similarity	NPD3748	Approved
0.7433	Intermediate Similarity	NPD7871	Phase 2
0.7433	Intermediate Similarity	NPD7870	Phase 2
0.7427	Intermediate Similarity	NPD7229	Phase 3
0.7419	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1613	Approved
0.7419	Intermediate Similarity	NPD6823	Phase 2
0.7418	Intermediate Similarity	NPD6534	Approved
0.7418	Intermediate Similarity	NPD6535	Approved
0.7407	Intermediate Similarity	NPD7701	Phase 2
0.7405	Intermediate Similarity	NPD5408	Approved
0.7405	Intermediate Similarity	NPD5404	Approved
0.7405	Intermediate Similarity	NPD5405	Approved
0.7405	Intermediate Similarity	NPD5406	Approved
0.7403	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7458	Discontinued
0.7391	Intermediate Similarity	NPD6190	Approved
0.7386	Intermediate Similarity	NPD4908	Phase 1
0.7386	Intermediate Similarity	NPD7240	Approved
0.7384	Intermediate Similarity	NPD3926	Phase 2
0.7384	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7801	Approved
0.7378	Intermediate Similarity	NPD920	Approved
0.7368	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2798	Approved
0.7368	Intermediate Similarity	NPD1247	Approved
0.7358	Intermediate Similarity	NPD2344	Approved
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.733	Intermediate Similarity	NPD5953	Discontinued
0.733	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7874	Approved
0.7329	Intermediate Similarity	NPD7003	Approved
0.7322	Intermediate Similarity	NPD4363	Phase 3
0.7322	Intermediate Similarity	NPD4360	Phase 2
0.7317	Intermediate Similarity	NPD6273	Approved
0.7314	Intermediate Similarity	NPD7286	Phase 2
0.7312	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7700	Phase 2
0.7297	Intermediate Similarity	NPD7699	Phase 2
0.7292	Intermediate Similarity	NPD7783	Phase 2
0.7292	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3764	Approved
0.7285	Intermediate Similarity	NPD4749	Approved
0.7267	Intermediate Similarity	NPD1243	Approved
0.7267	Intermediate Similarity	NPD2654	Approved
0.7256	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD919	Approved
0.7249	Intermediate Similarity	NPD8320	Phase 1
0.7249	Intermediate Similarity	NPD8319	Approved
0.7241	Intermediate Similarity	NPD2403	Approved
0.7233	Intermediate Similarity	NPD7033	Discontinued
0.7208	Intermediate Similarity	NPD9494	Approved
0.7208	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3620	Phase 2
0.7197	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7685	Pre-registration
0.7179	Intermediate Similarity	NPD2313	Discontinued
0.7178	Intermediate Similarity	NPD2309	Approved
0.7161	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD1610	Phase 2
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD447	Suspended
0.7151	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1283	Approved
0.7117	Intermediate Similarity	NPD8166	Discontinued
0.7105	Intermediate Similarity	NPD3972	Approved
0.7105	Intermediate Similarity	NPD9269	Phase 2
0.7101	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2424	Discontinued
0.7097	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4361	Phase 2
0.7089	Intermediate Similarity	NPD4060	Phase 1
0.7081	Intermediate Similarity	NPD6212	Phase 3
0.7081	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6213	Phase 3
0.7076	Intermediate Similarity	NPD5353	Approved
0.7072	Intermediate Similarity	NPD7090	Clinical (unspecified phase)

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