NPASS Compound

Structure

CID305157 OpenBabel06191716112D 21 24 0 0 1 0 0 0 0 0999 V2000 1.0800 -3.2033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4689 3.0855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3319 -2.5435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9474 1.3294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3282 0.5025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3379 0.4467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0140 -1.5980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8935 1.0136 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7522 1.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8947 -0.0160 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9433 -1.2865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1170 2.0073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5833 -0.7790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4638 -0.8353 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9462 -0.3158 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4945 2.7879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5576 -0.7618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1042 2.1561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2096 -0.4047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8897 -1.6021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 18 1 0 0 0 0 3 7 2 0 0 0 0 4 5 2 0 0 0 0 6 9 2 0 0 0 0 6 19 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 4 1 1 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 1 0 0 0 11 15 1 6 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 13 21 1 0 0 0 0 14 19 1 1 0 0 0 14 20 1 0 0 0 0 15 5 1 1 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.08
Volume:	273.329
LogP:	1.683
LogD:	1.217
LogS:	-3.051
# Rotatable Bonds:	2
TPSA:	71.06
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.405
Synthetic Accessibility Score:	5.608
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.899
MDCK Permeability:	3.7111258279765025e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.968
Plasma Protein Binding (PPB):	29.739856719970703%
Volume Distribution (VD):	2.041
Pgp-substrate:	54.56660842895508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.704
CYP1A2-substrate:	0.753
CYP2C19-inhibitor:	0.28
CYP2C19-substrate:	0.375
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.66
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	11.929
Half-life (T1/2):	0.316

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.648
Drug-inuced Liver Injury (DILI):	0.299
AMES Toxicity:	0.981
Rat Oral Acute Toxicity:	0.973
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.525
Carcinogencity:	0.943
Eye Corrosion:	0.087
Eye Irritation:	0.1
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC305157

Natural Product ID:	NPC305157
*Common Name:**	Isoplumericin
IUPAC Name:	n.a.
Synonyms:	Isoplumericin
Standard InCHIKey:	VFXXNAVZODKBIW-SIEBBUFOSA-N
Standard InCHI:	InChI=1S/C15H14O6/c1-3-7-11-15(21-13(7)17)5-4-8-9(12(16)18-2)6-19-14(20-11)10(8)15/h3-6,8,10-11,14H,1-2H3/b7-3-/t8-,10-,11+,14-,15+/m1/s1
SMILES:	COC(=O)C1=CO[C@H]2[C@H]3[C@@H]1C=C[C@@]13OC(=O)/C(=CC)/[C@@H]1O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463014
PubChem CID:	5281543
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25832441]
NPO40011	Allamanda schottii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3379414]
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9428163]
NPO40860	Himatanthus fallax	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9428163]
NPO29820	Allemanda cathartica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29820	Allemanda cathartica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3446	Acanthaster planci	Species	Acanthasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18031	Russula vesca	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16254	Backhousia angustifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15966	Sassafras officinalis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23695	Setosphaeria turcica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3990	Acacia salicina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10438	Tanacetum nubigenum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2591	Io fluvialis	Species	Pleuroceridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9524	Kalanchoe blossfeldiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16377	Juniperus ashei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18768	Haliclona tubifera	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6746	Blighia welwitschii	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17373.1	Cunninghamia lanceolata var. konishii	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17707	Dioscorea villosa	Species	Dioscoreaceae	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
ED50	1
IC50	3
Others	4

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	T/C	=	145.0	%	PMID[564419]
NPT726	Cell Line	M109	Mus musculus	IC50	=	25.0	ug.mL-1	PMID[564420]
NPT140	Organism	Artemia	Artemia	LC50	=	1.7	ppm	PMID[564419]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.7	ug ml-1	PMID[564419]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	44.0	%	PMID[564419]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	42.0	ug ml-1	PMID[564420]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	1410.0	nM	PMID[564421]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	3170.0	nM	PMID[564421]

☑ 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 NPC305157 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	265
0.1-0.2	1462
0.2-0.3	5086
0.3-0.4	9054
0.4-0.5	15373
0.5-0.6	7786
0.6-0.7	3201
0.7-0.8	463
0.8-0.85	3
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC307846
0.9118	High Similarity	NPC475960
0.901	High Similarity	NPC474917
0.8208	Intermediate Similarity	NPC469401
0.8155	Intermediate Similarity	NPC279561
0.8077	Intermediate Similarity	NPC469402
0.7981	Intermediate Similarity	NPC208233
0.7963	Intermediate Similarity	NPC254538
0.7963	Intermediate Similarity	NPC474285
0.7961	Intermediate Similarity	NPC35498
0.7822	Intermediate Similarity	NPC80875
0.7778	Intermediate Similarity	NPC203659
0.7767	Intermediate Similarity	NPC473316
0.7767	Intermediate Similarity	NPC476267
0.7767	Intermediate Similarity	NPC473330
0.7767	Intermediate Similarity	NPC140543
0.7757	Intermediate Similarity	NPC13171
0.7757	Intermediate Similarity	NPC195510
0.7745	Intermediate Similarity	NPC261607
0.7745	Intermediate Similarity	NPC300312
0.7745	Intermediate Similarity	NPC111114
0.7719	Intermediate Similarity	NPC277583
0.77	Intermediate Similarity	NPC231889
0.7699	Intermediate Similarity	NPC473535
0.7685	Intermediate Similarity	NPC475871
0.7685	Intermediate Similarity	NPC475945
0.7685	Intermediate Similarity	NPC110989
0.767	Intermediate Similarity	NPC179746
0.767	Intermediate Similarity	NPC81419
0.7664	Intermediate Similarity	NPC474742
0.7647	Intermediate Similarity	NPC312042
0.7647	Intermediate Similarity	NPC475748
0.7647	Intermediate Similarity	NPC62815
0.7642	Intermediate Similarity	NPC187268
0.7642	Intermediate Similarity	NPC473307
0.7627	Intermediate Similarity	NPC287236
0.7624	Intermediate Similarity	NPC473151
0.7615	Intermediate Similarity	NPC100487
0.7615	Intermediate Similarity	NPC474741
0.7596	Intermediate Similarity	NPC474338
0.7596	Intermediate Similarity	NPC475832
0.7596	Intermediate Similarity	NPC471147
0.7596	Intermediate Similarity	NPC475927
0.7593	Intermediate Similarity	NPC310804
0.7593	Intermediate Similarity	NPC474747
0.7593	Intermediate Similarity	NPC261117
0.7593	Intermediate Similarity	NPC225353
0.7593	Intermediate Similarity	NPC149371
0.7593	Intermediate Similarity	NPC86077
0.7573	Intermediate Similarity	NPC74103
0.7573	Intermediate Similarity	NPC70595
0.7573	Intermediate Similarity	NPC123177
0.7573	Intermediate Similarity	NPC150978
0.7573	Intermediate Similarity	NPC12172
0.7573	Intermediate Similarity	NPC208886
0.7573	Intermediate Similarity	NPC284185
0.757	Intermediate Similarity	NPC288876
0.7549	Intermediate Similarity	NPC166919
0.7549	Intermediate Similarity	NPC151770
0.7547	Intermediate Similarity	NPC153559
0.7547	Intermediate Similarity	NPC471462
0.7525	Intermediate Similarity	NPC475703
0.7525	Intermediate Similarity	NPC74139
0.7524	Intermediate Similarity	NPC304886
0.7524	Intermediate Similarity	NPC475659
0.7522	Intermediate Similarity	NPC474750
0.7521	Intermediate Similarity	NPC476107
0.75	Intermediate Similarity	NPC471145
0.75	Intermediate Similarity	NPC47880
0.75	Intermediate Similarity	NPC477511
0.75	Intermediate Similarity	NPC135776
0.75	Intermediate Similarity	NPC471146
0.75	Intermediate Similarity	NPC38154
0.75	Intermediate Similarity	NPC476300
0.75	Intermediate Similarity	NPC264477
0.75	Intermediate Similarity	NPC475912
0.7477	Intermediate Similarity	NPC124181
0.7477	Intermediate Similarity	NPC473326
0.7477	Intermediate Similarity	NPC90819
0.7476	Intermediate Similarity	NPC51004
0.7476	Intermediate Similarity	NPC253144
0.7458	Intermediate Similarity	NPC163693
0.7458	Intermediate Similarity	NPC147635
0.7456	Intermediate Similarity	NPC222834
0.7455	Intermediate Similarity	NPC471143
0.7455	Intermediate Similarity	NPC477510
0.7455	Intermediate Similarity	NPC86095
0.7453	Intermediate Similarity	NPC17585
0.7453	Intermediate Similarity	NPC473859
0.7434	Intermediate Similarity	NPC235014
0.7431	Intermediate Similarity	NPC250545
0.7431	Intermediate Similarity	NPC471599
0.7429	Intermediate Similarity	NPC477131
0.7426	Intermediate Similarity	NPC284902
0.7411	Intermediate Similarity	NPC10150
0.7407	Intermediate Similarity	NPC477512
0.7404	Intermediate Similarity	NPC30515
0.7404	Intermediate Similarity	NPC184463
0.7404	Intermediate Similarity	NPC470379
0.7404	Intermediate Similarity	NPC20713
0.7404	Intermediate Similarity	NPC470373
0.74	Intermediate Similarity	NPC41856
0.7395	Intermediate Similarity	NPC473228
0.7395	Intermediate Similarity	NPC204731
0.7395	Intermediate Similarity	NPC470829
0.7391	Intermediate Similarity	NPC470120
0.7387	Intermediate Similarity	NPC243998
0.7387	Intermediate Similarity	NPC223450
0.7387	Intermediate Similarity	NPC153095
0.7383	Intermediate Similarity	NPC40812
0.7379	Intermediate Similarity	NPC307411
0.7364	Intermediate Similarity	NPC475873
0.7358	Intermediate Similarity	NPC471142
0.7358	Intermediate Similarity	NPC241407
0.7358	Intermediate Similarity	NPC90121
0.7358	Intermediate Similarity	NPC14961
0.7358	Intermediate Similarity	NPC291709
0.7358	Intermediate Similarity	NPC224689
0.7358	Intermediate Similarity	NPC270013
0.7358	Intermediate Similarity	NPC167893
0.7358	Intermediate Similarity	NPC193645
0.7358	Intermediate Similarity	NPC48803
0.7358	Intermediate Similarity	NPC36954
0.7358	Intermediate Similarity	NPC275960
0.735	Intermediate Similarity	NPC23046
0.7347	Intermediate Similarity	NPC223904
0.7345	Intermediate Similarity	NPC187876
0.7339	Intermediate Similarity	NPC4637
0.7339	Intermediate Similarity	NPC28304
0.7339	Intermediate Similarity	NPC98859
0.7339	Intermediate Similarity	NPC298255
0.7339	Intermediate Similarity	NPC133907
0.7339	Intermediate Similarity	NPC185141
0.7339	Intermediate Similarity	NPC473332
0.7339	Intermediate Similarity	NPC110443
0.7339	Intermediate Similarity	NPC46998
0.7339	Intermediate Similarity	NPC128733
0.7339	Intermediate Similarity	NPC219038
0.7333	Intermediate Similarity	NPC212486
0.7327	Intermediate Similarity	NPC38468
0.7327	Intermediate Similarity	NPC215364
0.7327	Intermediate Similarity	NPC319795
0.7327	Intermediate Similarity	NPC50362
0.7321	Intermediate Similarity	NPC148270
0.7321	Intermediate Similarity	NPC26617
0.7321	Intermediate Similarity	NPC197813
0.7321	Intermediate Similarity	NPC80338
0.7315	Intermediate Similarity	NPC471144
0.7315	Intermediate Similarity	NPC261377
0.7315	Intermediate Similarity	NPC83895
0.7315	Intermediate Similarity	NPC141191
0.7315	Intermediate Similarity	NPC187761
0.7315	Intermediate Similarity	NPC308567
0.7315	Intermediate Similarity	NPC54843
0.7315	Intermediate Similarity	NPC255592
0.7311	Intermediate Similarity	NPC151616
0.7308	Intermediate Similarity	NPC49342
0.7308	Intermediate Similarity	NPC71533
0.7308	Intermediate Similarity	NPC106510
0.7308	Intermediate Similarity	NPC251385
0.7304	Intermediate Similarity	NPC471570
0.73	Intermediate Similarity	NPC170286
0.73	Intermediate Similarity	NPC39588
0.73	Intermediate Similarity	NPC272814
0.73	Intermediate Similarity	NPC475947
0.729	Intermediate Similarity	NPC301596
0.729	Intermediate Similarity	NPC476315
0.729	Intermediate Similarity	NPC306041
0.729	Intermediate Similarity	NPC299396
0.729	Intermediate Similarity	NPC172998
0.7288	Intermediate Similarity	NPC475309
0.7288	Intermediate Similarity	NPC13710
0.7282	Intermediate Similarity	NPC202672
0.7264	Intermediate Similarity	NPC262133
0.7264	Intermediate Similarity	NPC303942
0.7264	Intermediate Similarity	NPC474035
0.7264	Intermediate Similarity	NPC167219
0.7264	Intermediate Similarity	NPC323008
0.7264	Intermediate Similarity	NPC81386
0.7264	Intermediate Similarity	NPC289004
0.7264	Intermediate Similarity	NPC470010
0.7264	Intermediate Similarity	NPC57405
0.7264	Intermediate Similarity	NPC470013
0.7264	Intermediate Similarity	NPC71589
0.7257	Intermediate Similarity	NPC110701
0.7255	Intermediate Similarity	NPC50637
0.7255	Intermediate Similarity	NPC107787
0.7248	Intermediate Similarity	NPC255677
0.7248	Intermediate Similarity	NPC306344
0.7248	Intermediate Similarity	NPC473146
0.7248	Intermediate Similarity	NPC22149
0.7238	Intermediate Similarity	NPC131209
0.7238	Intermediate Similarity	NPC133698
0.7236	Intermediate Similarity	NPC298841
0.7232	Intermediate Similarity	NPC170432
0.7232	Intermediate Similarity	NPC314244
0.7227	Intermediate Similarity	NPC475834
0.7227	Intermediate Similarity	NPC474179
0.7222	Intermediate Similarity	NPC169205
0.7222	Intermediate Similarity	NPC471140

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 NPC305157 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	1956
0.2-0.3	3803
0.3-0.4	2134
0.4-0.5	758
0.5-0.6	208
0.6-0.7	51
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7358	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1695	Approved
0.7107	Intermediate Similarity	NPD8513	Phase 3
0.7103	Intermediate Similarity	NPD5282	Discontinued
0.6967	Remote Similarity	NPD8517	Approved
0.6967	Remote Similarity	NPD8516	Approved
0.6967	Remote Similarity	NPD8515	Approved
0.6957	Remote Similarity	NPD6686	Approved
0.6838	Remote Similarity	NPD6371	Approved
0.678	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6053	Discontinued
0.6696	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6606	Remote Similarity	NPD7983	Approved
0.6589	Remote Similarity	NPD7319	Approved
0.6587	Remote Similarity	NPD7642	Approved
0.6512	Remote Similarity	NPD7736	Approved
0.6509	Remote Similarity	NPD1694	Approved
0.6508	Remote Similarity	NPD6370	Approved
0.6484	Remote Similarity	NPD7507	Approved
0.6457	Remote Similarity	NPD7829	Approved
0.6457	Remote Similarity	NPD7830	Approved
0.6434	Remote Similarity	NPD7078	Approved
0.6434	Remote Similarity	NPD8074	Phase 3
0.6406	Remote Similarity	NPD7492	Approved
0.6404	Remote Similarity	NPD4225	Approved
0.6396	Remote Similarity	NPD5779	Approved
0.6396	Remote Similarity	NPD5778	Approved
0.637	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7838	Discovery
0.6357	Remote Similarity	NPD8451	Approved
0.6357	Remote Similarity	NPD6616	Approved
0.6349	Remote Similarity	NPD6054	Approved
0.6308	Remote Similarity	NPD8448	Approved
0.6308	Remote Similarity	NPD8293	Discontinued
0.6299	Remote Similarity	NPD6015	Approved
0.6299	Remote Similarity	NPD6016	Approved
0.6299	Remote Similarity	NPD7503	Approved
0.6296	Remote Similarity	NPD4249	Approved
0.625	Remote Similarity	NPD5988	Approved
0.624	Remote Similarity	NPD7115	Discovery
0.6239	Remote Similarity	NPD4250	Approved
0.6239	Remote Similarity	NPD4251	Approved
0.6228	Remote Similarity	NPD7839	Suspended
0.6226	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5209	Approved
0.6218	Remote Similarity	NPD6008	Approved
0.6216	Remote Similarity	NPD5785	Approved
0.6207	Remote Similarity	NPD6648	Approved
0.619	Remote Similarity	NPD7641	Discontinued
0.6172	Remote Similarity	NPD8444	Approved
0.6168	Remote Similarity	NPD7154	Phase 3
0.6165	Remote Similarity	NPD8391	Approved
0.6165	Remote Similarity	NPD8392	Approved
0.6165	Remote Similarity	NPD8390	Approved
0.6154	Remote Similarity	NPD8342	Approved
0.6154	Remote Similarity	NPD5344	Discontinued
0.6154	Remote Similarity	NPD8341	Approved
0.6154	Remote Similarity	NPD8340	Approved
0.6154	Remote Similarity	NPD8299	Approved
0.6136	Remote Similarity	NPD8336	Approved
0.6136	Remote Similarity	NPD8337	Approved
0.6124	Remote Similarity	NPD8080	Discontinued
0.6111	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD6059	Approved
0.6077	Remote Similarity	NPD8328	Phase 3
0.6074	Remote Similarity	NPD8338	Approved
0.6055	Remote Similarity	NPD5363	Approved
0.6033	Remote Similarity	NPD6412	Phase 2
0.6033	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5786	Approved
0.5984	Remote Similarity	NPD6009	Approved
0.5982	Remote Similarity	NPD6101	Approved
0.5982	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD6319	Approved
0.5938	Remote Similarity	NPD7327	Approved
0.5938	Remote Similarity	NPD7328	Approved
0.5923	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD8033	Approved
0.5923	Remote Similarity	NPD8269	Approved
0.5923	Remote Similarity	NPD8268	Approved
0.5923	Remote Similarity	NPD8266	Approved
0.5923	Remote Similarity	NPD8267	Approved
0.5891	Remote Similarity	NPD7516	Approved
0.5887	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7260	Phase 2
0.5877	Remote Similarity	NPD6411	Approved
0.5872	Remote Similarity	NPD5362	Discontinued
0.5859	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD8377	Approved
0.5846	Remote Similarity	NPD8294	Approved
0.5833	Remote Similarity	NPD5369	Approved
0.5818	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD8379	Approved
0.5802	Remote Similarity	NPD8378	Approved
0.5802	Remote Similarity	NPD8296	Approved
0.5802	Remote Similarity	NPD8335	Approved
0.5802	Remote Similarity	NPD8380	Approved
0.5794	Remote Similarity	NPD6882	Approved
0.578	Remote Similarity	NPD4270	Approved
0.578	Remote Similarity	NPD6435	Approved
0.578	Remote Similarity	NPD4269	Approved
0.576	Remote Similarity	NPD2067	Discontinued
0.5748	Remote Similarity	NPD4632	Approved
0.5748	Remote Similarity	NPD8133	Approved
0.5738	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD7500	Approved
0.5725	Remote Similarity	NPD6845	Suspended
0.5714	Remote Similarity	NPD7638	Approved
0.5693	Remote Similarity	NPD5956	Approved
0.5669	Remote Similarity	NPD8297	Approved
0.5667	Remote Similarity	NPD7639	Approved
0.5667	Remote Similarity	NPD7640	Approved
0.5662	Remote Similarity	NPD6033	Approved
0.5645	Remote Similarity	NPD5697	Approved
0.5636	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD7637	Suspended
0.56	Remote Similarity	NPD6881	Approved
0.56	Remote Similarity	NPD6899	Approved
0.56	Remote Similarity	NPD2685	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