NPASS Compound

Structure

CID320147 OpenBabel06191716152D 44 56 0 0 1 0 0 0 0 0999 V2000 -1.9504 -0.7103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2595 1.1652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4130 -1.1263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9915 1.3200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8588 -0.0368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2595 0.8557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7840 -0.8689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7234 1.1652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6729 -0.7841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4411 -0.1881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9599 1.3697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2822 0.5239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7827 0.8959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5115 0.2251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2428 -0.7941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6816 -0.3925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2334 1.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9960 -0.1251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8348 -0.6030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1815 -0.3669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8337 0.4935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8794 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2844 1.4421 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6939 -0.1649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2298 0.2206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9915 0.7010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6924 -0.1955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7234 0.8557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2343 0.8951 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1126 0.1564 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1881 1.4411 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5084 0.0769 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1893 0.3447 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6193 0.3658 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2256 -0.0490 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2044 0.7595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1382 0.8940 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9271 0.3982 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7838 -0.0536 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.2982 -0.0853 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.0634 0.0619 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4934 0.6486 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0191 -0.4265 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 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 25 2 0 0 0 0 6 26 2 0 0 0 0 7 27 2 0 0 0 0 8 28 2 0 0 0 0 9 15 1 0 0 0 0 9 22 2 0 0 0 0 10 16 1 0 0 0 0 10 21 2 0 0 0 0 11 13 1 0 0 0 0 11 37 1 0 0 0 0 12 14 1 0 0 0 0 12 38 1 0 0 0 0 13 39 1 0 0 0 0 14 40 1 0 0 0 0 15 43 1 0 0 0 0 16 44 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 21 1 0 0 0 0 19 39 1 0 0 0 0 20 22 1 0 0 0 0 20 40 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 17 1 6 0 0 0 23 31 1 0 0 0 0 24 18 1 6 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 25 37 1 0 0 0 0 26 28 1 0 0 0 0 26 38 1 0 0 0 0 27 41 1 0 0 0 0 28 42 1 0 0 0 0 29 37 1 1 0 0 0 29 39 1 0 0 0 0 30 38 1 1 0 0 0 30 40 1 0 0 0 0 31 33 1 0 0 0 0 31 36 1 0 0 0 0 32 34 1 0 0 0 0 32 35 1 0 0 0 0 33 37 1 0 0 0 0 33 41 1 0 0 0 0 34 38 1 0 0 0 0 34 42 1 0 0 0 0 35 41 1 0 0 0 0 35 43 1 0 0 0 0 36 42 1 0 0 0 0 36 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.32
Volume:	595.046
LogP:	4.589
LogD:	4.299
LogS:	-4.238
# Rotatable Bonds:	0
TPSA:	31.42
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	13
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.431
Synthetic Accessibility Score:	7.376
Fsp3:	0.579
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.792
MDCK Permeability:	3.122085763607174e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.916
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	86.45201110839844%
Volume Distribution (VD):	1.422
Pgp-substrate:	11.69597053527832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.725
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.523
CYP2D6-substrate:	0.331
CYP3A4-inhibitor:	0.687
CYP3A4-substrate:	0.9

ADMET: Excretion

Clearance (CL):	10.281
Half-life (T1/2):	0.075

ADMET: Toxicity

hERG Blockers:	0.736
Human Hepatotoxicity (H-HT):	0.587
Drug-inuced Liver Injury (DILI):	0.877
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.918
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.052
Carcinogencity:	0.7
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC320147

Natural Product ID:	NPC320147
*Common Name:**	Caracurine V
IUPAC Name:	n.a.
Synonyms:	Caracurine V
Standard InCHIKey:	CIRUUTNLDXXBKU-HCKBHOMASA-N
Standard InCHI:	InChI=1S/C38H40N4O2/c1-3-7-27-25(5-1)37-11-13-39-19-21-10-16-44-36-31(23(21)17-29(37)39)33(37)41(27)35-32-24-18-30-38(12-14-40(30)20-22(24)9-15-43-35)26-6-2-4-8-28(26)42(36)34(32)38/h1-10,23-24,29-36H,11-20H2/t23-,24-,29-,30-,31+,32+,33-,34-,35+,36+,37+,38+/m0/s1
SMILES:	C1C=C2CN3CC[C@]45[C@@H]6[C@H]([C@@H](O1)N1c7ccccc7[C@]78[C@@H]1[C@@H]1[C@H](N6c6c5cccc6)OCC=C5[C@@H]1C[C@@H]8N(CC7)C5)[C@H]2C[C@H]34
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL380352
PubChem CID:	168927
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos 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
NPO6440	Strychnos dolichothyrsa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4766	Strychnos afzelii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6440	Strychnos dolichothyrsa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4766	Strychnos afzelii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4766	Strychnos afzelii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6440	Strychnos dolichothyrsa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6440	Strychnos dolichothyrsa	Species	Loganiaceae	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
EC50	2
Ki	2
Others	2

Activity Type	# Activity
Individual Protein	4
Others	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2843	Individual Protein	Muscarinic acetylcholine receptor M2	Sus scrofa	pEC0.5	=	6.36	n.a.	PMID[569048]
NPT2843	Individual Protein	Muscarinic acetylcholine receptor M2	Sus scrofa	EC0.25	=	95.8	n.a.	PMID[569048]
NPT263	Individual Protein	Muscarinic acetylcholine receptor M2	Homo sapiens	EC50	=	436.52	nM	PMID[569049]
NPT2843	Individual Protein	Muscarinic acetylcholine receptor M2	Sus scrofa	EC50	=	436.0	nM	PMID[569050]
NPT3922	Protein Complex	Acetylcholine receptor	Torpedo californica	Ki	<	100000.0	nM	PMID[569049]
NPT2	Others	Unspecified		Ki	>	100000.0	nM	PMID[569050]

☑ 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 NPC320147 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	517
0.1-0.2	1873
0.2-0.3	7552
0.3-0.4	23626
0.4-0.5	7121
0.5-0.6	1660
0.6-0.7	287
0.7-0.8	51
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8951	High Similarity	NPC475420
0.8795	High Similarity	NPC473880
0.8571	High Similarity	NPC473743
0.8389	Intermediate Similarity	NPC162440
0.8352	Intermediate Similarity	NPC285841
0.8343	Intermediate Similarity	NPC476095
0.8198	Intermediate Similarity	NPC475097
0.8075	Intermediate Similarity	NPC329833
0.7931	Intermediate Similarity	NPC214626
0.7931	Intermediate Similarity	NPC251212
0.7931	Intermediate Similarity	NPC139085
0.7598	Intermediate Similarity	NPC260075
0.7545	Intermediate Similarity	NPC264589
0.7514	Intermediate Similarity	NPC286994
0.7458	Intermediate Similarity	NPC475248
0.7458	Intermediate Similarity	NPC63047
0.744	Intermediate Similarity	NPC469735
0.7411	Intermediate Similarity	NPC126066
0.7409	Intermediate Similarity	NPC52801
0.738	Intermediate Similarity	NPC22689
0.738	Intermediate Similarity	NPC105055
0.7371	Intermediate Similarity	NPC225319
0.7368	Intermediate Similarity	NPC206592
0.733	Intermediate Similarity	NPC99632
0.733	Intermediate Similarity	NPC282339
0.7267	Intermediate Similarity	NPC475763
0.7193	Intermediate Similarity	NPC469740
0.7135	Intermediate Similarity	NPC469741
0.7079	Intermediate Similarity	NPC248117
0.7076	Intermediate Similarity	NPC116519
0.7062	Intermediate Similarity	NPC113946
0.7041	Intermediate Similarity	NPC138830
0.7041	Intermediate Similarity	NPC67904
0.7022	Intermediate Similarity	NPC193410
0.698	Remote Similarity	NPC475422
0.6973	Remote Similarity	NPC203202
0.6973	Remote Similarity	NPC264482
0.6966	Remote Similarity	NPC61013
0.6957	Remote Similarity	NPC96901
0.6941	Remote Similarity	NPC186284
0.6941	Remote Similarity	NPC22082
0.6882	Remote Similarity	NPC243162
0.6881	Remote Similarity	NPC87755
0.6878	Remote Similarity	NPC256288
0.6868	Remote Similarity	NPC472106
0.6851	Remote Similarity	NPC472120
0.6851	Remote Similarity	NPC472101
0.6842	Remote Similarity	NPC2933
0.6823	Remote Similarity	NPC229484
0.6816	Remote Similarity	NPC477157
0.6816	Remote Similarity	NPC477156
0.6806	Remote Similarity	NPC259626
0.6796	Remote Similarity	NPC475602
0.6793	Remote Similarity	NPC224970
0.6793	Remote Similarity	NPC167724
0.6793	Remote Similarity	NPC223595
0.6788	Remote Similarity	NPC292675
0.678	Remote Similarity	NPC243756
0.6778	Remote Similarity	NPC123241
0.6771	Remote Similarity	NPC473615
0.6758	Remote Similarity	NPC85651
0.6744	Remote Similarity	NPC223242
0.672	Remote Similarity	NPC321211
0.672	Remote Similarity	NPC99043
0.672	Remote Similarity	NPC6974
0.672	Remote Similarity	NPC218594
0.6719	Remote Similarity	NPC52262
0.6704	Remote Similarity	NPC478076
0.6702	Remote Similarity	NPC159963
0.6682	Remote Similarity	NPC139373
0.6667	Remote Similarity	NPC293458
0.6667	Remote Similarity	NPC186669
0.665	Remote Similarity	NPC473178
0.6648	Remote Similarity	NPC472100
0.6648	Remote Similarity	NPC36495
0.6636	Remote Similarity	NPC131977
0.6633	Remote Similarity	NPC470483
0.6633	Remote Similarity	NPC25401
0.663	Remote Similarity	NPC29285
0.6629	Remote Similarity	NPC318086
0.6612	Remote Similarity	NPC201424
0.6596	Remote Similarity	NPC242269
0.6587	Remote Similarity	NPC159815
0.6576	Remote Similarity	NPC472117
0.6571	Remote Similarity	NPC472027
0.6566	Remote Similarity	NPC470485
0.6564	Remote Similarity	NPC181928
0.6564	Remote Similarity	NPC14994
0.6556	Remote Similarity	NPC122106
0.6555	Remote Similarity	NPC473757
0.6546	Remote Similarity	NPC322621
0.6532	Remote Similarity	NPC301501
0.6522	Remote Similarity	NPC471946
0.6522	Remote Similarity	NPC471951
0.6522	Remote Similarity	NPC477158
0.6517	Remote Similarity	NPC212799
0.6502	Remote Similarity	NPC469450
0.6498	Remote Similarity	NPC475258
0.6494	Remote Similarity	NPC130251
0.6489	Remote Similarity	NPC469915
0.648	Remote Similarity	NPC473177
0.648	Remote Similarity	NPC109787
0.648	Remote Similarity	NPC21425
0.6476	Remote Similarity	NPC473006
0.6474	Remote Similarity	NPC329338
0.6474	Remote Similarity	NPC469726
0.6471	Remote Similarity	NPC279527
0.6471	Remote Similarity	NPC473005
0.6471	Remote Similarity	NPC214960
0.6452	Remote Similarity	NPC475338
0.6452	Remote Similarity	NPC909
0.645	Remote Similarity	NPC221687
0.6448	Remote Similarity	NPC469536
0.6444	Remote Similarity	NPC469452
0.6444	Remote Similarity	NPC469451
0.6441	Remote Similarity	NPC311330
0.6432	Remote Similarity	NPC474058
0.6432	Remote Similarity	NPC309531
0.6432	Remote Similarity	NPC472102
0.6429	Remote Similarity	NPC145754
0.6425	Remote Similarity	NPC477065
0.6421	Remote Similarity	NPC476425
0.642	Remote Similarity	NPC477155
0.641	Remote Similarity	NPC97584
0.6409	Remote Similarity	NPC66936
0.6409	Remote Similarity	NPC154602
0.6398	Remote Similarity	NPC176983
0.6398	Remote Similarity	NPC286871
0.6393	Remote Similarity	NPC473297
0.6388	Remote Similarity	NPC329932
0.6382	Remote Similarity	NPC276430
0.6378	Remote Similarity	NPC307396
0.6378	Remote Similarity	NPC276085
0.6377	Remote Similarity	NPC477174
0.6372	Remote Similarity	NPC10653
0.6372	Remote Similarity	NPC318525
0.6368	Remote Similarity	NPC34717
0.6364	Remote Similarity	NPC475915
0.6349	Remote Similarity	NPC33507
0.6343	Remote Similarity	NPC471506
0.6324	Remote Similarity	NPC222029
0.6316	Remote Similarity	NPC471950
0.6316	Remote Similarity	NPC472118
0.6316	Remote Similarity	NPC471945
0.6305	Remote Similarity	NPC90967
0.6304	Remote Similarity	NPC161827
0.6296	Remote Similarity	NPC472114
0.6296	Remote Similarity	NPC472115
0.6293	Remote Similarity	NPC127178
0.6293	Remote Similarity	NPC476493
0.6271	Remote Similarity	NPC301760
0.6269	Remote Similarity	NPC56618
0.6269	Remote Similarity	NPC476441
0.6262	Remote Similarity	NPC471512
0.6257	Remote Similarity	NPC255229
0.6257	Remote Similarity	NPC81229
0.6256	Remote Similarity	NPC97100
0.6256	Remote Similarity	NPC473375
0.625	Remote Similarity	NPC473298
0.6238	Remote Similarity	NPC475259
0.6235	Remote Similarity	NPC478079
0.6225	Remote Similarity	NPC232130
0.622	Remote Similarity	NPC477173
0.6214	Remote Similarity	NPC475489
0.6203	Remote Similarity	NPC63210
0.6203	Remote Similarity	NPC148468
0.6203	Remote Similarity	NPC243673
0.6203	Remote Similarity	NPC97380
0.6203	Remote Similarity	NPC310403
0.6203	Remote Similarity	NPC263709
0.6202	Remote Similarity	NPC477179
0.6201	Remote Similarity	NPC469537
0.6198	Remote Similarity	NPC126492
0.6196	Remote Similarity	NPC285381
0.6193	Remote Similarity	NPC472104
0.6193	Remote Similarity	NPC19679
0.619	Remote Similarity	NPC470488
0.6188	Remote Similarity	NPC471386
0.6186	Remote Similarity	NPC24594
0.6186	Remote Similarity	NPC472122
0.6173	Remote Similarity	NPC187827
0.6173	Remote Similarity	NPC472105
0.6172	Remote Similarity	NPC477181
0.6172	Remote Similarity	NPC477178
0.6172	Remote Similarity	NPC477180
0.6172	Remote Similarity	NPC254850
0.6172	Remote Similarity	NPC470484
0.6167	Remote Similarity	NPC472103
0.6166	Remote Similarity	NPC477185
0.6164	Remote Similarity	NPC471564
0.6161	Remote Similarity	NPC470491
0.6158	Remote Similarity	NPC70172
0.6158	Remote Similarity	NPC470069
0.6158	Remote Similarity	NPC52059
0.6158	Remote Similarity	NPC302001
0.6157	Remote Similarity	NPC469722
0.6154	Remote Similarity	NPC285941
0.6154	Remote Similarity	NPC477187
0.6154	Remote Similarity	NPC476326
0.6154	Remote Similarity	NPC162730

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 NPC320147 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	647
0.2-0.3	809
0.3-0.4	2357
0.4-0.5	4055
0.5-0.6	963
0.6-0.7	26
0.7-0.8	5
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8171	Intermediate Similarity	NPD8402	Approved
0.8171	Intermediate Similarity	NPD8401	Approved
0.8171	Intermediate Similarity	NPD8400	Approved
0.676	Remote Similarity	NPD5743	Approved
0.676	Remote Similarity	NPD5741	Approved
0.676	Remote Similarity	NPD5742	Approved
0.6704	Remote Similarity	NPD4120	Approved
0.6704	Remote Similarity	NPD4121	Phase 3
0.6387	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD8240	Discontinued
0.6348	Remote Similarity	NPD7487	Discontinued
0.6333	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5600	Discontinued
0.6307	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD6070	Approved
0.6258	Remote Similarity	NPD6069	Approved
0.625	Remote Similarity	NPD6357	Discontinued
0.6237	Remote Similarity	NPD8630	Approved
0.6226	Remote Similarity	NPD4116	Approved
0.6226	Remote Similarity	NPD7633	Discontinued
0.6224	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6622	Phase 1
0.6221	Remote Similarity	NPD6489	Phase 3
0.6209	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD4644	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD7479	Phase 2
0.6195	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD6879	Phase 2
0.6173	Remote Similarity	NPD6878	Phase 2
0.6169	Remote Similarity	NPD6281	Approved
0.6166	Remote Similarity	NPD5997	Discontinued
0.6164	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6025	Phase 1
0.6135	Remote Similarity	NPD5629	Discontinued
0.6118	Remote Similarity	NPD6320	Approved
0.6111	Remote Similarity	NPD8281	Discontinued
0.6094	Remote Similarity	NPD3983	Phase 3
0.6094	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD5657	Phase 3
0.6074	Remote Similarity	NPD2913	Approved
0.6074	Remote Similarity	NPD2914	Approved
0.6071	Remote Similarity	NPD7824	Approved
0.607	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6789	Approved
0.5991	Remote Similarity	NPD7790	Approved
0.5991	Remote Similarity	NPD7952	Approved
0.5991	Remote Similarity	NPD7950	Approved
0.5991	Remote Similarity	NPD7791	Approved
0.5991	Remote Similarity	NPD7953	Approved
0.5991	Remote Similarity	NPD7789	Approved
0.5991	Remote Similarity	NPD7951	Approved
0.599	Remote Similarity	NPD4796	Discontinued
0.5989	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7731	Approved
0.5982	Remote Similarity	NPD7730	Approved
0.5977	Remote Similarity	NPD4365	Phase 2
0.597	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD8353	Approved
0.5968	Remote Similarity	NPD8355	Approved
0.5968	Remote Similarity	NPD7606	Phase 3
0.5964	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD7271	Approved
0.5959	Remote Similarity	NPD6037	Discontinued
0.5956	Remote Similarity	NPD7295	Approved
0.5956	Remote Similarity	NPD5932	Phase 3
0.5956	Remote Similarity	NPD5931	Phase 3
0.5956	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD5933	Phase 3
0.5954	Remote Similarity	NPD7247	Discontinued
0.5951	Remote Similarity	NPD2039	Approved
0.5951	Remote Similarity	NPD2038	Approved
0.595	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD814	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD5184	Approved
0.5932	Remote Similarity	NPD5182	Approved
0.5932	Remote Similarity	NPD5185	Approved
0.593	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD2326	Approved
0.5922	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7262	Phase 1
0.5916	Remote Similarity	NPD6524	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD8358	Approved
0.5914	Remote Similarity	NPD1405	Approved
0.5911	Remote Similarity	NPD6978	Phase 2
0.5911	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD8354	Approved
0.5902	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.5901	Remote Similarity	NPD4114	Approved
0.5901	Remote Similarity	NPD4115	Approved
0.5895	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.5892	Remote Similarity	NPD7478	Approved
0.5888	Remote Similarity	NPD7940	Phase 3
0.5885	Remote Similarity	NPD19	Approved
0.5885	Remote Similarity	NPD1742	Approved
0.5885	Remote Similarity	NPD1743	Approved
0.5882	Remote Similarity	NPD6455	Phase 3
0.5879	Remote Similarity	NPD5180	Approved
0.5879	Remote Similarity	NPD7881	Approved
0.5879	Remote Similarity	NPD5181	Approved
0.5879	Remote Similarity	NPD5179	Approved
0.5879	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD7599	Phase 2
0.5859	Remote Similarity	NPD5104	Approved
0.5856	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.5848	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD7082	Approved
0.5847	Remote Similarity	NPD4430	Phase 2
0.5846	Remote Similarity	NPD7890	Discontinued
0.5846	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD5631	Phase 3
0.5842	Remote Similarity	NPD7877	Suspended
0.5839	Remote Similarity	NPD3545	Approved
0.5839	Remote Similarity	NPD3546	Approved
0.5838	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5318	Discontinued
0.5833	Remote Similarity	NPD7600	Phase 2
0.5829	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5913	Phase 3
0.5825	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD7259	Approved
0.5815	Remote Similarity	NPD2387	Approved
0.5812	Remote Similarity	NPD8060	Phase 1
0.5805	Remote Similarity	NPD6900	Discontinued
0.5802	Remote Similarity	NPD5253	Approved
0.5792	Remote Similarity	NPD6566	Discontinued
0.5787	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD3975	Discontinued
0.5787	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.5777	Remote Similarity	NPD4499	Approved
0.5763	Remote Similarity	NPD7921	Approved
0.5761	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD5526	Phase 2
0.5761	Remote Similarity	NPD6301	Phase 2
0.5758	Remote Similarity	NPD4571	Approved
0.5758	Remote Similarity	NPD7854	Phase 2
0.5758	Remote Similarity	NPD4572	Approved
0.5758	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD4573	Approved
0.5758	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.5754	Remote Similarity	NPD7200	Approved
0.575	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD8128	Discontinued
0.5746	Remote Similarity	NPD6358	Phase 2
0.5742	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD5518	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD5531	Discontinued
0.5735	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD6227	Discontinued
0.573	Remote Similarity	NPD7099	Approved
0.5729	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5938	Phase 3
0.5729	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD8025	Phase 2
0.5726	Remote Similarity	NPD8016	Phase 3
0.5726	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.5723	Remote Similarity	NPD7250	Approved
0.5723	Remote Similarity	NPD7249	Approved
0.5714	Remote Similarity	NPD2622	Approved
0.5714	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3240	Phase 2
0.5706	Remote Similarity	NPD8263	Discontinued
0.5701	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.57	Remote Similarity	NPD8063	Discontinued
0.57	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD6738	Phase 2
0.5699	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD6737	Phase 2
0.5699	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD5579	Approved
0.5698	Remote Similarity	NPD5576	Approved
0.5693	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.5693	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD3789	Approved
0.5692	Remote Similarity	NPD7734	Approved
0.5687	Remote Similarity	NPD4735	Approved
0.5687	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.5687	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.5687	Remote Similarity	NPD7572	Phase 2
0.5687	Remote Similarity	NPD4734	Approved
0.5685	Remote Similarity	NPD6379	Discontinued
0.5685	Remote Similarity	NPD7580	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