NPASS Compound

Structure

CID99632 OpenBabel06191715442D 25 30 0 0 1 0 0 0 0 0999 V2000 1.0066 3.6714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1915 1.7669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5484 1.1487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9500 2.1141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4777 1.7669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1915 0.5305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9368 1.2363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9292 0.1368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2537 -0.0940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0722 1.7182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1963 2.5644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5988 2.4206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5661 1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1207 1.1487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8071 1.0772 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4777 0.5305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5151 2.2324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4164 1.2591 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1701 0.8088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5775 1.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6521 0.2903 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4295 2.1369 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 2.1767 1.6650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3455 3.0938 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 3 2 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 4 11 1 0 0 0 0 5 14 2 0 0 0 0 6 16 2 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 21 1 6 0 0 0 16 22 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 19 1 6 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 19 7 1 1 0 0 0 20 21 1 6 0 0 0 21 9 1 1 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.2
Volume:	349.462
LogP:	2.315
LogD:	2.326
LogS:	-4.171
# Rotatable Bonds:	2
TPSA:	41.57
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.8
Synthetic Accessibility Score:	5.897
Fsp3:	0.667
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:	-4.834
MDCK Permeability:	3.33190182573162e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.932
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.752
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	48.86363983154297%
Volume Distribution (VD):	1.811
Pgp-substrate:	59.14368438720703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.121
CYP1A2-substrate:	0.819
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.873
CYP2C9-inhibitor:	0.247
CYP2C9-substrate:	0.161
CYP2D6-inhibitor:	0.874
CYP2D6-substrate:	0.884
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.717

ADMET: Excretion

Clearance (CL):	6.206
Half-life (T1/2):	0.331

ADMET: Toxicity

hERG Blockers:	0.182
Human Hepatotoxicity (H-HT):	0.216
Drug-inuced Liver Injury (DILI):	0.064
AMES Toxicity:	0.157
Rat Oral Acute Toxicity:	0.804
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.705
Carcinogencity:	0.211
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.761

Download Data

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

Natural Product: NPC99632

Natural Product ID:	NPC99632
*Common Name:**	IYLRRIUNGGQRTN-DDVIMMDMSA-N
IUPAC Name:	n.a.
Synonyms:	16-Epikopsinine
Standard InCHIKey:	IYLRRIUNGGQRTN-DDVIMMDMSA-N
Standard InCHI:	InChI=1S/C21H26N2O2/c1-25-17(24)15-13-19-7-4-11-23-12-10-20(18(19)23)14-5-2-3-6-16(14)22-21(15,20)9-8-19/h2-3,5-6,15,18,22H,4,7-13H2,1H3/t15-,18+,19-,20-,21-/m1/s1
SMILES:	COC(=O)[C@H]1C[C@@]23CCCN4CC[C@@]5(c6ccccc6N[C@]15CC2)[C@H]34
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253984
PubChem CID:	7069832
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003755] Aspidofractine alkaloids

*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
NPO18923	Coleus xanthanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027731]
NPO10	Alexandrium ostenfeldii	Species	Pyrocystaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872129]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17939738]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	leaf and stem-bark	Pahang, Malaysia	1996-JUL	PMID[18078327]
NPO10	Alexandrium ostenfeldii	Species	Pyrocystaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19572609]
NPO21142	Kopsia fruticosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18923	Coleus xanthanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21640	Pygmaeopremna herbacea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO18923	Coleus xanthanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21142	Kopsia fruticosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28069.1	Artemisia cana subsp. viscidula	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17662	Scutellaria glabrata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3679	Psilocybe baeocystis	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17897	Streptomyces albospinus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21313	Rabdosia lasiocarpa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1824	Callitris rhomboidea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28069.1	Artemisia cana subsp. viscidula	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2744	Aphloia madagascariensis	Species	Aphloiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21640	Pygmaeopremna herbacea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10	Alexandrium ostenfeldii	Species	Pyrocystaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7972	Solaster endeca	Species	Solasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13485	Prismatomeris sessiliflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8358	Senecio halimifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20028	Lethariella sernanderi	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21142	Kopsia fruticosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18923	Coleus xanthanthus	Species	Lamiaceae	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	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[494221]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[494221]

☑ 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 NPC99632 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	282
0.1-0.2	1400
0.2-0.3	5380
0.3-0.4	23127
0.4-0.5	8908
0.5-0.6	2859
0.6-0.7	549
0.7-0.8	150
0.8-0.85	27
0.85-0.9	5
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC282339
0.9536	High Similarity	NPC225319
0.891	High Similarity	NPC248117
0.8846	High Similarity	NPC193410
0.8795	High Similarity	NPC52262
0.8782	High Similarity	NPC61013
0.8634	High Similarity	NPC224970
0.8634	High Similarity	NPC167724
0.8634	High Similarity	NPC223595
0.8608	High Similarity	NPC36495
0.8598	High Similarity	NPC203202
0.8598	High Similarity	NPC264482
0.8544	High Similarity	NPC123241
0.85	High Similarity	NPC293458
0.8442	Intermediate Similarity	NPC264589
0.8354	Intermediate Similarity	NPC478076
0.8274	Intermediate Similarity	NPC99043
0.8274	Intermediate Similarity	NPC6974
0.8274	Intermediate Similarity	NPC218594
0.8253	Intermediate Similarity	NPC139085
0.8253	Intermediate Similarity	NPC251212
0.8253	Intermediate Similarity	NPC214626
0.8232	Intermediate Similarity	NPC214960
0.8232	Intermediate Similarity	NPC279527
0.8204	Intermediate Similarity	NPC329338
0.8204	Intermediate Similarity	NPC469726
0.8129	Intermediate Similarity	NPC159963
0.8113	Intermediate Similarity	NPC475763
0.8107	Intermediate Similarity	NPC186669
0.8086	Intermediate Similarity	NPC113946
0.8079	Intermediate Similarity	NPC221687
0.8046	Intermediate Similarity	NPC181928
0.8046	Intermediate Similarity	NPC14994
0.8011	Intermediate Similarity	NPC25401
0.7988	Intermediate Similarity	NPC472102
0.7988	Intermediate Similarity	NPC201424
0.7988	Intermediate Similarity	NPC309531
0.7977	Intermediate Similarity	NPC97584
0.7939	Intermediate Similarity	NPC469741
0.7895	Intermediate Similarity	NPC260075
0.7853	Intermediate Similarity	NPC473298
0.7833	Intermediate Similarity	NPC473375
0.7833	Intermediate Similarity	NPC97100
0.7814	Intermediate Similarity	NPC471512
0.7778	Intermediate Similarity	NPC34717
0.7778	Intermediate Similarity	NPC475097
0.7744	Intermediate Similarity	NPC473297
0.7738	Intermediate Similarity	NPC472106
0.7725	Intermediate Similarity	NPC472101
0.7725	Intermediate Similarity	NPC472120
0.7719	Intermediate Similarity	NPC476425
0.7719	Intermediate Similarity	NPC473743
0.7719	Intermediate Similarity	NPC285622
0.7706	Intermediate Similarity	NPC472118
0.7692	Intermediate Similarity	NPC90967
0.7692	Intermediate Similarity	NPC162440
0.7676	Intermediate Similarity	NPC162730
0.7654	Intermediate Similarity	NPC22689
0.7654	Intermediate Similarity	NPC105055
0.7633	Intermediate Similarity	NPC475420
0.763	Intermediate Similarity	NPC476441
0.7619	Intermediate Similarity	NPC286871
0.7619	Intermediate Similarity	NPC472117
0.7616	Intermediate Similarity	NPC96901
0.7611	Intermediate Similarity	NPC22476
0.7611	Intermediate Similarity	NPC203628
0.7595	Intermediate Similarity	NPC130251
0.7581	Intermediate Similarity	NPC474116
0.7561	Intermediate Similarity	NPC243756
0.7556	Intermediate Similarity	NPC5630
0.7556	Intermediate Similarity	NPC329858
0.7545	Intermediate Similarity	NPC222029
0.753	Intermediate Similarity	NPC161827
0.7515	Intermediate Similarity	NPC176983
0.7514	Intermediate Similarity	NPC473880
0.7487	Intermediate Similarity	NPC137589
0.7485	Intermediate Similarity	NPC472114
0.7485	Intermediate Similarity	NPC472115
0.7455	Intermediate Similarity	NPC66936
0.7446	Intermediate Similarity	NPC303214
0.7444	Intermediate Similarity	NPC21425
0.7443	Intermediate Similarity	NPC321211
0.744	Intermediate Similarity	NPC153694
0.744	Intermediate Similarity	NPC211525
0.7421	Intermediate Similarity	NPC477065
0.7412	Intermediate Similarity	NPC472121
0.7396	Intermediate Similarity	NPC243673
0.7396	Intermediate Similarity	NPC63210
0.7396	Intermediate Similarity	NPC148468
0.7396	Intermediate Similarity	NPC310403
0.7396	Intermediate Similarity	NPC263709
0.7396	Intermediate Similarity	NPC97380
0.7386	Intermediate Similarity	NPC476326
0.7381	Intermediate Similarity	NPC29285
0.738	Intermediate Similarity	NPC138830
0.738	Intermediate Similarity	NPC67904
0.7366	Intermediate Similarity	NPC138615
0.7366	Intermediate Similarity	NPC132874
0.7366	Intermediate Similarity	NPC218733
0.7366	Intermediate Similarity	NPC265642
0.7363	Intermediate Similarity	NPC314333
0.7353	Intermediate Similarity	NPC474058
0.7349	Intermediate Similarity	NPC154602
0.7341	Intermediate Similarity	NPC475248
0.7341	Intermediate Similarity	NPC63047
0.733	Intermediate Similarity	NPC320147
0.7329	Intermediate Similarity	NPC301760
0.7329	Intermediate Similarity	NPC186284
0.7329	Intermediate Similarity	NPC22082
0.7326	Intermediate Similarity	NPC470069
0.7326	Intermediate Similarity	NPC52059
0.7316	Intermediate Similarity	NPC329833
0.7305	Intermediate Similarity	NPC122106
0.7296	Intermediate Similarity	NPC471123
0.7289	Intermediate Similarity	NPC473329
0.7267	Intermediate Similarity	NPC243162
0.7263	Intermediate Similarity	NPC476428
0.7249	Intermediate Similarity	NPC232600
0.7239	Intermediate Similarity	NPC469537
0.7238	Intermediate Similarity	NPC259626
0.7238	Intermediate Similarity	NPC322621
0.7216	Intermediate Similarity	NPC177261
0.7211	Intermediate Similarity	NPC1464
0.7207	Intermediate Similarity	NPC11149
0.7186	Intermediate Similarity	NPC288110
0.7186	Intermediate Similarity	NPC318086
0.7184	Intermediate Similarity	NPC278887
0.7182	Intermediate Similarity	NPC2933
0.7181	Intermediate Similarity	NPC100863
0.7181	Intermediate Similarity	NPC52557
0.7176	Intermediate Similarity	NPC469536
0.7152	Intermediate Similarity	NPC116519
0.7143	Intermediate Similarity	NPC476095
0.7135	Intermediate Similarity	NPC475147
0.7135	Intermediate Similarity	NPC185742
0.7135	Intermediate Similarity	NPC87714
0.7135	Intermediate Similarity	NPC475847
0.7127	Intermediate Similarity	NPC256288
0.7119	Intermediate Similarity	NPC21752
0.7119	Intermediate Similarity	NPC276993
0.7119	Intermediate Similarity	NPC298851
0.7119	Intermediate Similarity	NPC293255
0.7119	Intermediate Similarity	NPC181138
0.7119	Intermediate Similarity	NPC210415
0.7111	Intermediate Similarity	NPC286994
0.7105	Intermediate Similarity	NPC475489
0.7102	Intermediate Similarity	NPC469915
0.7101	Intermediate Similarity	NPC285381
0.7098	Intermediate Similarity	NPC246140
0.7098	Intermediate Similarity	NPC195787
0.7091	Intermediate Similarity	NPC311330
0.7088	Intermediate Similarity	NPC472119
0.7081	Intermediate Similarity	NPC474059
0.7065	Intermediate Similarity	NPC285841
0.7035	Intermediate Similarity	NPC104345
0.7016	Intermediate Similarity	NPC81654
0.7016	Intermediate Similarity	NPC249150
0.7016	Intermediate Similarity	NPC79129
0.7016	Intermediate Similarity	NPC313985
0.7016	Intermediate Similarity	NPC49196
0.7016	Intermediate Similarity	NPC195461
0.7011	Intermediate Similarity	NPC473615
0.6994	Remote Similarity	NPC276085
0.6994	Remote Similarity	NPC471122
0.699	Remote Similarity	NPC475133
0.6985	Remote Similarity	NPC189661
0.6984	Remote Similarity	NPC245916
0.6973	Remote Similarity	NPC229484
0.6964	Remote Similarity	NPC212799
0.6957	Remote Similarity	NPC472209
0.6954	Remote Similarity	NPC68650
0.6954	Remote Similarity	NPC234999
0.6954	Remote Similarity	NPC269449
0.6942	Remote Similarity	NPC473458
0.6941	Remote Similarity	NPC206592
0.694	Remote Similarity	NPC477159
0.6935	Remote Similarity	NPC175474
0.6935	Remote Similarity	NPC63199
0.6935	Remote Similarity	NPC102338
0.6935	Remote Similarity	NPC196251
0.6935	Remote Similarity	NPC292675
0.6935	Remote Similarity	NPC111602
0.6927	Remote Similarity	NPC115588
0.6923	Remote Similarity	NPC469896
0.6923	Remote Similarity	NPC109787
0.6915	Remote Similarity	NPC55493
0.6911	Remote Similarity	NPC50503
0.6898	Remote Similarity	NPC472112
0.6891	Remote Similarity	NPC469732
0.689	Remote Similarity	NPC469560
0.6889	Remote Similarity	NPC13367
0.6886	Remote Similarity	NPC472103
0.6884	Remote Similarity	NPC159815
0.6884	Remote Similarity	NPC475778
0.6884	Remote Similarity	NPC119722
0.6881	Remote Similarity	NPC77777
0.6879	Remote Similarity	NPC477157
0.6879	Remote Similarity	NPC477156
0.6878	Remote Similarity	NPC81802
0.6878	Remote Similarity	NPC247735

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 NPC99632 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	537
0.2-0.3	795
0.3-0.4	1748
0.4-0.5	3761
0.5-0.6	1917
0.6-0.7	214
0.7-0.8	9
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
0.7389	Intermediate Similarity	NPD5184	Approved
0.7389	Intermediate Similarity	NPD5185	Approved
0.7389	Intermediate Similarity	NPD5182	Approved
0.7363	Intermediate Similarity	NPD4499	Approved
0.7234	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7487	Discontinued
0.7117	Intermediate Similarity	NPD3625	Discontinued
0.7086	Intermediate Similarity	NPD2994	Approved
0.7066	Intermediate Similarity	NPD7478	Approved
0.7043	Intermediate Similarity	NPD5504	Discontinued
0.7043	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7606	Phase 3
0.7035	Intermediate Similarity	NPD8630	Approved
0.7022	Intermediate Similarity	NPD7854	Phase 2
0.702	Intermediate Similarity	NPD2115	Approved
0.702	Intermediate Similarity	NPD2116	Approved
0.702	Intermediate Similarity	NPD2117	Pre-registration
0.7017	Intermediate Similarity	NPD4329	Approved
0.7017	Intermediate Similarity	NPD4330	Approved
0.7016	Intermediate Similarity	NPD4601	Approved
0.7016	Intermediate Similarity	NPD4600	Approved
0.6978	Remote Similarity	NPD3470	Approved
0.6978	Remote Similarity	NPD3471	Approved
0.697	Remote Similarity	NPD6768	Approved
0.6959	Remote Similarity	NPD2790	Discontinued
0.6948	Remote Similarity	NPD2946	Phase 2
0.6943	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3030	Approved
0.6928	Remote Similarity	NPD3031	Approved
0.6928	Remote Similarity	NPD3032	Approved
0.6923	Remote Similarity	NPD5942	Approved
0.6923	Remote Similarity	NPD5941	Approved
0.6906	Remote Similarity	NPD3792	Approved
0.6903	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4120	Approved
0.686	Remote Similarity	NPD4121	Phase 3
0.686	Remote Similarity	NPD5086	Approved
0.6854	Remote Similarity	NPD2037	Approved
0.6845	Remote Similarity	NPD7295	Approved
0.6833	Remote Similarity	NPD5997	Discontinued
0.6826	Remote Similarity	NPD7082	Approved
0.6826	Remote Similarity	NPD2820	Phase 3
0.6826	Remote Similarity	NPD5024	Approved
0.6821	Remote Similarity	NPD5743	Approved
0.6821	Remote Similarity	NPD5742	Approved
0.6821	Remote Similarity	NPD5741	Approved
0.6816	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6416	Phase 2
0.6798	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5993	Phase 1
0.679	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5918	Discontinued
0.6786	Remote Similarity	NPD7259	Approved
0.678	Remote Similarity	NPD3790	Phase 2
0.6778	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD2431	Approved
0.6778	Remote Similarity	NPD2432	Approved
0.6766	Remote Similarity	NPD2365	Approved
0.6765	Remote Similarity	NPD1802	Approved
0.6765	Remote Similarity	NPD1801	Approved
0.676	Remote Similarity	NPD2455	Approved
0.676	Remote Similarity	NPD2454	Approved
0.6753	Remote Similarity	NPD4500	Approved
0.6753	Remote Similarity	NPD4501	Approved
0.6752	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5931	Phase 3
0.6746	Remote Similarity	NPD5933	Phase 3
0.6746	Remote Similarity	NPD5932	Phase 3
0.6742	Remote Similarity	NPD5430	Discontinued
0.6739	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6342	Discontinued
0.6727	Remote Similarity	NPD6358	Phase 2
0.6725	Remote Similarity	NPD4888	Discontinued
0.6722	Remote Similarity	NPD7795	Phase 2
0.6705	Remote Similarity	NPD8402	Approved
0.6705	Remote Similarity	NPD8400	Approved
0.6705	Remote Similarity	NPD7599	Phase 2
0.6705	Remote Similarity	NPD8401	Approved
0.6703	Remote Similarity	NPD3423	Phase 2
0.6703	Remote Similarity	NPD5466	Approved
0.6703	Remote Similarity	NPD3422	Phase 3
0.6687	Remote Similarity	NPD1626	Approved
0.6687	Remote Similarity	NPD3170	Approved
0.6686	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3782	Discontinued
0.6667	Remote Similarity	NPD1070	Approved
0.6667	Remote Similarity	NPD7600	Phase 2
0.6667	Remote Similarity	NPD2506	Approved
0.6667	Remote Similarity	NPD1069	Approved
0.6667	Remote Similarity	NPD6566	Discontinued
0.6667	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6489	Phase 3
0.6667	Remote Similarity	NPD8281	Discontinued
0.6645	Remote Similarity	NPD1373	Approved
0.6645	Remote Similarity	NPD1374	Approved
0.6645	Remote Similarity	NPD1370	Approved
0.6645	Remote Similarity	NPD1371	Approved
0.663	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7528	Approved
0.6627	Remote Similarity	NPD2670	Approved
0.6623	Remote Similarity	NPD2039	Approved
0.6623	Remote Similarity	NPD2038	Approved
0.6614	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4116	Approved
0.6598	Remote Similarity	NPD3828	Approved
0.6598	Remote Similarity	NPD7572	Phase 2
0.6597	Remote Similarity	NPD8240	Discontinued
0.6595	Remote Similarity	NPD7881	Approved
0.6591	Remote Similarity	NPD1663	Discontinued
0.659	Remote Similarity	NPD5748	Phase 2
0.6588	Remote Similarity	NPD2435	Approved
0.658	Remote Similarity	NPD4602	Approved
0.6578	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7581	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2404	Discontinued
0.6575	Remote Similarity	NPD7580	Phase 3
0.6573	Remote Similarity	NPD7244	Discontinued
0.6557	Remote Similarity	NPD3377	Discontinued
0.6556	Remote Similarity	NPD7036	Phase 3
0.6556	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7035	Approved
0.6554	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5982	Phase 2
0.655	Remote Similarity	NPD6017	Discontinued
0.6543	Remote Similarity	NPD4412	Phase 2
0.6543	Remote Similarity	NPD4549	Discontinued
0.6541	Remote Similarity	NPD1360	Approved
0.6541	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD5181	Approved
0.6536	Remote Similarity	NPD5180	Approved
0.6536	Remote Similarity	NPD5179	Approved
0.6532	Remote Similarity	NPD4682	Phase 2
0.6529	Remote Similarity	NPD1625	Approved
0.6522	Remote Similarity	NPD7940	Phase 3
0.6517	Remote Similarity	NPD2427	Approved
0.6514	Remote Similarity	NPD2948	Discontinued
0.6512	Remote Similarity	NPD4041	Approved
0.6509	Remote Similarity	NPD2010	Phase 3
0.6505	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5263	Approved
0.6503	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6571	Approved
0.6497	Remote Similarity	NPD6570	Approved
0.6492	Remote Similarity	NPD7234	Approved
0.6492	Remote Similarity	NPD7233	Approved
0.649	Remote Similarity	NPD7633	Discontinued
0.6489	Remote Similarity	NPD7962	Phase 2
0.6486	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD2844	Phase 3
0.6484	Remote Similarity	NPD3468	Approved
0.6478	Remote Similarity	NPD4178	Approved
0.6478	Remote Similarity	NPD4176	Approved
0.6477	Remote Similarity	NPD7570	Approved
0.6477	Remote Similarity	NPD7569	Approved
0.6467	Remote Similarity	NPD6073	Approved
0.6465	Remote Similarity	NPD6238	Discontinued
0.6453	Remote Similarity	NPD6622	Phase 1
0.6452	Remote Similarity	NPD5600	Discontinued
0.645	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD5183	Approved
0.6448	Remote Similarity	NPD5186	Approved
0.6441	Remote Similarity	NPD8358	Approved
0.6436	Remote Similarity	NPD2916	Discontinued
0.6433	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6295	Approved
0.6429	Remote Similarity	NPD6294	Approved
0.6425	Remote Similarity	NPD3884	Discontinued
0.6424	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD5581	Approved
0.641	Remote Similarity	NPD5162	Approved
0.6409	Remote Similarity	NPD8007	Approved
0.6409	Remote Similarity	NPD8008	Approved
0.6404	Remote Similarity	NPD7105	Phase 1
0.6402	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1405	Approved
0.6396	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD1109	Approved
0.6391	Remote Similarity	NPD1110	Approved
0.6391	Remote Similarity	NPD7254	Discontinued
0.6386	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD1527	Phase 2
0.6383	Remote Similarity	NPD6879	Phase 2
0.6383	Remote Similarity	NPD6878	Phase 2
0.6383	Remote Similarity	NPD5473	Discontinued
0.6379	Remote Similarity	NPD7088	Discontinued
0.6378	Remote Similarity	NPD750	Phase 2
0.6374	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5928	Phase 1
0.6368	Remote Similarity	NPD5426	Phase 3

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