NPASS Compound

Structure

NPC223242 OpenBabel07101718222D 52 64 0 0 1 0 0 0 0 0999 V2000 1.2460 2.4575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2572 3.0763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1308 -3.5793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0444 -3.1725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8441 0.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3218 -2.9915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8441 -0.0425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1489 -2.1780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9780 1.4575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6009 -3.4366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0662 -2.2049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4350 -1.0526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9620 -3.2112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2451 0.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9832 -2.9266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0857 -1.5403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2572 -2.7927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0096 -3.8467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4681 0.6649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1933 -2.3296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7409 -3.0302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7572 0.4782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6409 -2.1078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3743 -0.6071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1878 -2.4342 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7572 0.4782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4264 -1.9970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9780 -0.5425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3399 -1.5902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1120 0.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9638 -3.4556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1120 -0.0425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2572 -0.3878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7756 -1.6251 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2572 1.3442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0098 -2.2976 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7572 -1.2538 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4877 -0.6506 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2134 -1.4161 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5517 -2.9695 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2572 -0.3878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7572 -1.2538 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7701 -1.5206 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2354 -0.5957 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8228 -2.3098 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.4482 -2.2049 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.3689 -0.7116 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2572 1.3442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2460 1.4575 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7572 2.2103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6288 -3.9978 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 49 1 0 0 0 0 2 50 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 8 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 27 2 0 0 0 0 7 28 1 0 0 0 0 8 29 2 0 0 0 0 9 30 2 0 0 0 0 10 15 1 0 0 0 0 10 31 1 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 45 1 0 0 0 0 16 45 1 0 0 0 0 17 46 1 0 0 0 0 18 51 1 0 0 0 0 19 52 1 0 0 0 0 21 25 1 0 0 0 0 21 40 1 0 0 0 0 22 26 1 0 0 0 0 22 41 1 0 0 0 0 23 39 1 0 0 0 0 23 46 1 0 0 0 0 24 39 1 0 0 0 0 24 47 1 0 0 0 0 25 20 1 1 0 0 0 25 34 1 0 0 0 0 26 33 2 0 0 0 0 26 35 1 0 0 0 0 27 29 1 0 0 0 0 27 42 1 0 0 0 0 28 32 2 0 0 0 0 28 43 1 0 0 0 0 29 44 1 0 0 0 0 30 32 1 0 0 0 0 30 49 1 0 0 0 0 31 40 1 6 0 0 0 31 51 1 0 0 0 0 32 47 1 0 0 0 0 33 42 1 0 0 0 0 33 44 1 0 0 0 0 34 43 1 6 0 0 0 34 47 1 0 0 0 0 35 48 2 0 0 0 0 35 50 1 0 0 0 0 36 40 1 1 0 0 0 36 43 1 0 0 0 0 36 45 1 0 0 0 0 37 41 1 6 0 0 0 37 42 1 0 0 0 0 37 46 1 0 0 0 0 38 39 1 1 0 0 0 38 41 1 0 0 0 0 38 52 1 0 0 0 0 39 20 1 1 0 0 0 40 13 1 6 0 0 0 41 14 1 1 0 0 0 42 11 1 6 0 0 0 43 12 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	182.06
Volume:	180.279
LogP:	0.879
LogD:	0.933
LogS:	-1.898
# Rotatable Bonds:	2
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	2.647
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.376
MDCK Permeability:	3.32594063365832e-05
Pgp-inhibitor:	0.096
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.177
Plasma Protein Binding (PPB):	82.53572845458984%
Volume Distribution (VD):	1.066
Pgp-substrate:	9.255499839782715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.951
CYP2C19-substrate:	0.716
CYP2C9-inhibitor:	0.579
CYP2C9-substrate:	0.314
CYP2D6-inhibitor:	0.936
CYP2D6-substrate:	0.037
CYP3A4-inhibitor:	0.595
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	6.454
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.503
Drug-inuced Liver Injury (DILI):	0.153
AMES Toxicity:	0.288
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.76
Skin Sensitization:	0.922
Carcinogencity:	0.658
Eye Corrosion:	0.75
Eye Irritation:	0.985
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC223242

Natural Product ID:	NPC223242
*Common Name:**	Deoxyvobtusine
IUPAC Name:	n.a.
Synonyms:	Deoxyvobtusine
Standard InCHIKey:	IWNZQRZTZRLAFI-AYMQSLGUSA-N
Standard InCHI:	InChI=1S/C43H50N4O5/c1-49-30-9-5-7-28-32(30)47-24-39(20-25-21-40-13-18-51-31(40)10-15-45-16-12-43(28,34(25)47)36(40)45)23-46-17-11-42-27-6-3-4-8-29(27)44-33(42)26(35(48)50-2)22-41(37(42)46)14-19-52-38(39)41/h3-9,25,31,34,36-38,44H,10-24H2,1-2H3/t25-,31+,34+,36+,37+,38+,39+,40-,41+,42+,43+/m1/s1
SMILES:	COc1cccc2c1N1C[C@]3(C[C@@H]4C[C@]56CCO[C@H]5CCN5CC[C@]2([C@@H]14)[C@H]65)CN1CC[C@]24c5ccccc5NC2=C(C[C@@]2(CCO[C@@H]32)[C@H]14)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797184
PubChem CID:	56673596
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002755] Aspidospermatan-type 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
NPO32722	voacanga globosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21546135]

☑ 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
MIC	1
Others	1

Activity Type	# Activity
Individual Protein	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	87000.0	nM	PMID[474618]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	>	50.0	ug.mL-1	PMID[474618]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	Inhibition	=	13.0	%	PMID[474618]
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	6200.0	nM	PMID[474618]
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	7726.81	nM	PMID[474618]

☑ 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 NPC223242 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	401
0.1-0.2	1858
0.2-0.3	5540
0.3-0.4	12769
0.4-0.5	16251
0.5-0.6	5055
0.6-0.7	668
0.7-0.8	125
0.8-0.85	9
0.85-0.9	9
0.9-0.95	3
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9902	High Similarity	NPC139373
0.9713	High Similarity	NPC131977
0.9667	High Similarity	NPC301501
0.9621	High Similarity	NPC469450
0.9531	High Similarity	NPC469452
0.9531	High Similarity	NPC469451
0.9442	High Similarity	NPC329932
0.8571	High Similarity	NPC469722
0.851	High Similarity	NPC195787
0.851	High Similarity	NPC246140
0.8119	Intermediate Similarity	NPC195636
0.8104	Intermediate Similarity	NPC1464
0.8082	Intermediate Similarity	NPC77777
0.8009	Intermediate Similarity	NPC476069
0.7948	Intermediate Similarity	NPC154922
0.7944	Intermediate Similarity	NPC87714
0.7892	Intermediate Similarity	NPC128476
0.7867	Intermediate Similarity	NPC19175
0.7805	Intermediate Similarity	NPC159963
0.7799	Intermediate Similarity	NPC25401
0.7783	Intermediate Similarity	NPC189661
0.7778	Intermediate Similarity	NPC113455
0.7754	Intermediate Similarity	NPC120239
0.7749	Intermediate Similarity	NPC476220
0.7749	Intermediate Similarity	NPC160113
0.774	Intermediate Similarity	NPC14994
0.7725	Intermediate Similarity	NPC151171
0.7714	Intermediate Similarity	NPC22476
0.7709	Intermediate Similarity	NPC231924
0.7668	Intermediate Similarity	NPC234772
0.7664	Intermediate Similarity	NPC138615
0.7664	Intermediate Similarity	NPC265642
0.7664	Intermediate Similarity	NPC218733
0.7664	Intermediate Similarity	NPC132874
0.7647	Intermediate Similarity	NPC203202
0.7647	Intermediate Similarity	NPC264482
0.7635	Intermediate Similarity	NPC329982
0.7617	Intermediate Similarity	NPC304837
0.7617	Intermediate Similarity	NPC476258
0.7615	Intermediate Similarity	NPC475147
0.761	Intermediate Similarity	NPC186669
0.7598	Intermediate Similarity	NPC476436
0.7593	Intermediate Similarity	NPC138830
0.7565	Intermediate Similarity	NPC471513
0.7564	Intermediate Similarity	NPC291173
0.7557	Intermediate Similarity	NPC475133
0.7555	Intermediate Similarity	NPC115588
0.7511	Intermediate Similarity	NPC476429
0.75	Intermediate Similarity	NPC5630
0.7489	Intermediate Similarity	NPC473458
0.7488	Intermediate Similarity	NPC6974
0.7488	Intermediate Similarity	NPC21425
0.7444	Intermediate Similarity	NPC269449
0.7404	Intermediate Similarity	NPC99043
0.7404	Intermediate Similarity	NPC218594
0.7378	Intermediate Similarity	NPC119722
0.7352	Intermediate Similarity	NPC67904
0.735	Intermediate Similarity	NPC477397
0.7346	Intermediate Similarity	NPC97584
0.7336	Intermediate Similarity	NPC288110
0.7309	Intermediate Similarity	NPC478075
0.7302	Intermediate Similarity	NPC203628
0.7301	Intermediate Similarity	NPC127996
0.7294	Intermediate Similarity	NPC162440
0.7273	Intermediate Similarity	NPC477393
0.7261	Intermediate Similarity	NPC222046
0.726	Intermediate Similarity	NPC100863
0.724	Intermediate Similarity	NPC232600
0.724	Intermediate Similarity	NPC469732
0.7229	Intermediate Similarity	NPC318525
0.7229	Intermediate Similarity	NPC10653
0.7225	Intermediate Similarity	NPC159815
0.722	Intermediate Similarity	NPC329833
0.7213	Intermediate Similarity	NPC477396
0.719	Intermediate Similarity	NPC477395
0.7174	Intermediate Similarity	NPC126556
0.7169	Intermediate Similarity	NPC303214
0.7163	Intermediate Similarity	NPC181928
0.716	Intermediate Similarity	NPC471303
0.7157	Intermediate Similarity	NPC248117
0.7143	Intermediate Similarity	NPC61013
0.713	Intermediate Similarity	NPC473005
0.7118	Intermediate Similarity	NPC473006
0.7108	Intermediate Similarity	NPC193410
0.7082	Intermediate Similarity	NPC472099
0.7078	Intermediate Similarity	NPC470485
0.7073	Intermediate Similarity	NPC17437
0.7071	Intermediate Similarity	NPC474192
0.7071	Intermediate Similarity	NPC475720
0.707	Intermediate Similarity	NPC476095
0.7067	Intermediate Similarity	NPC224970
0.7067	Intermediate Similarity	NPC167724
0.7067	Intermediate Similarity	NPC223595
0.7045	Intermediate Similarity	NPC34717
0.7033	Intermediate Similarity	NPC469734
0.7012	Intermediate Similarity	NPC478083
0.7005	Intermediate Similarity	NPC285841
0.6992	Remote Similarity	NPC81939
0.6991	Remote Similarity	NPC470484
0.6986	Remote Similarity	NPC470483
0.6982	Remote Similarity	NPC90967
0.698	Remote Similarity	NPC477067
0.698	Remote Similarity	NPC478082
0.6978	Remote Similarity	NPC52801
0.6978	Remote Similarity	NPC474077
0.6976	Remote Similarity	NPC123241
0.6968	Remote Similarity	NPC243626
0.6968	Remote Similarity	NPC230313
0.6967	Remote Similarity	NPC475816
0.6964	Remote Similarity	NPC475666
0.6962	Remote Similarity	NPC21638
0.6962	Remote Similarity	NPC477394
0.696	Remote Similarity	NPC477161
0.6957	Remote Similarity	NPC293458
0.6943	Remote Similarity	NPC477160
0.6941	Remote Similarity	NPC473298
0.6941	Remote Similarity	NPC474059
0.6939	Remote Similarity	NPC477066
0.6911	Remote Similarity	NPC473540
0.6911	Remote Similarity	NPC478081
0.6908	Remote Similarity	NPC237901
0.6908	Remote Similarity	NPC195788
0.6905	Remote Similarity	NPC478080
0.6901	Remote Similarity	NPC473105
0.6891	Remote Similarity	NPC122886
0.6875	Remote Similarity	NPC311906
0.6875	Remote Similarity	NPC282339
0.6875	Remote Similarity	NPC99632
0.6864	Remote Similarity	NPC22689
0.6864	Remote Similarity	NPC105055
0.6863	Remote Similarity	NPC191489
0.6854	Remote Similarity	NPC329338
0.6854	Remote Similarity	NPC469726
0.6851	Remote Similarity	NPC96321
0.6842	Remote Similarity	NPC268077
0.6835	Remote Similarity	NPC473007
0.6824	Remote Similarity	NPC284685
0.6822	Remote Similarity	NPC100734
0.6822	Remote Similarity	NPC315634
0.6822	Remote Similarity	NPC88923
0.681	Remote Similarity	NPC475420
0.6808	Remote Similarity	NPC473880
0.6808	Remote Similarity	NPC473743
0.6805	Remote Similarity	NPC260909
0.6802	Remote Similarity	NPC473004
0.6798	Remote Similarity	NPC207971
0.6787	Remote Similarity	NPC473008
0.6781	Remote Similarity	NPC472098
0.6779	Remote Similarity	NPC36495
0.6753	Remote Similarity	NPC329567
0.6753	Remote Similarity	NPC330683
0.6751	Remote Similarity	NPC219397
0.6744	Remote Similarity	NPC320147
0.6743	Remote Similarity	NPC98197
0.6735	Remote Similarity	NPC39370
0.6729	Remote Similarity	NPC293255
0.6729	Remote Similarity	NPC139085
0.6729	Remote Similarity	NPC21752
0.6729	Remote Similarity	NPC181138
0.6729	Remote Similarity	NPC298851
0.6729	Remote Similarity	NPC251212
0.6729	Remote Similarity	NPC210415
0.6729	Remote Similarity	NPC276993
0.6729	Remote Similarity	NPC214626
0.6721	Remote Similarity	NPC473186
0.6709	Remote Similarity	NPC10732
0.6698	Remote Similarity	NPC472114
0.6698	Remote Similarity	NPC472115
0.6696	Remote Similarity	NPC203972
0.6695	Remote Similarity	NPC152768
0.6695	Remote Similarity	NPC148183
0.6694	Remote Similarity	NPC478078
0.6694	Remote Similarity	NPC248903
0.6682	Remote Similarity	NPC52262
0.6681	Remote Similarity	NPC471950
0.6681	Remote Similarity	NPC475609
0.6681	Remote Similarity	NPC471945
0.6681	Remote Similarity	NPC161804
0.6667	Remote Similarity	NPC82541
0.6667	Remote Similarity	NPC225319
0.6667	Remote Similarity	NPC217294
0.6667	Remote Similarity	NPC33507
0.6667	Remote Similarity	NPC127178
0.6654	Remote Similarity	NPC152620
0.6653	Remote Similarity	NPC26928
0.6652	Remote Similarity	NPC471946
0.6652	Remote Similarity	NPC71124
0.6652	Remote Similarity	NPC471951
0.6651	Remote Similarity	NPC70172
0.6651	Remote Similarity	NPC476425
0.6639	Remote Similarity	NPC473041
0.6638	Remote Similarity	NPC471512
0.6637	Remote Similarity	NPC473569
0.6637	Remote Similarity	NPC141440
0.6626	Remote Similarity	NPC329631
0.6624	Remote Similarity	NPC25961
0.6623	Remote Similarity	NPC5374
0.6623	Remote Similarity	NPC244606
0.6623	Remote Similarity	NPC156728
0.6622	Remote Similarity	NPC471825

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 NPC223242 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	638
0.2-0.3	859
0.3-0.4	2158
0.4-0.5	3250
0.5-0.6	1816
0.6-0.7	199
0.7-0.8	1
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
0.7155	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8358	Approved
0.7067	Intermediate Similarity	NPD6644	Discontinued
0.6971	Remote Similarity	NPD6625	Approved
0.6947	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD8363	Approved
0.6938	Remote Similarity	NPD8364	Approved
0.6936	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6199	Discontinued
0.6908	Remote Similarity	NPD8465	Approved
0.6908	Remote Similarity	NPD8466	Approved
0.6908	Remote Similarity	NPD8467	Approved
0.69	Remote Similarity	NPD4082	Approved
0.6885	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4493	Discontinued
0.688	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7708	Approved
0.6858	Remote Similarity	NPD6238	Discontinued
0.6853	Remote Similarity	NPD4494	Approved
0.6853	Remote Similarity	NPD4492	Approved
0.6852	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD3006	Discontinued
0.684	Remote Similarity	NPD5860	Discontinued
0.6824	Remote Similarity	NPD7955	Approved
0.6824	Remote Similarity	NPD7956	Approved
0.6822	Remote Similarity	NPD7803	Approved
0.6806	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD8426	Approved
0.6805	Remote Similarity	NPD8459	Approved
0.6805	Remote Similarity	NPD8425	Approved
0.6805	Remote Similarity	NPD8460	Approved
0.6792	Remote Similarity	NPD5186	Approved
0.6792	Remote Similarity	NPD5183	Approved
0.6787	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4596	Phase 1
0.678	Remote Similarity	NPD8429	Approved
0.678	Remote Similarity	NPD8427	Approved
0.678	Remote Similarity	NPD8428	Approved
0.6753	Remote Similarity	NPD2907	Approved
0.6753	Remote Similarity	NPD2906	Approved
0.6753	Remote Similarity	NPD4859	Phase 1
0.6745	Remote Similarity	NPD2681	Approved
0.6745	Remote Similarity	NPD2680	Approved
0.6742	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1769	Discontinued
0.6728	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5071	Phase 2
0.6723	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5928	Phase 1
0.6696	Remote Similarity	NPD6874	Approved
0.6695	Remote Similarity	NPD3893	Discontinued
0.6682	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4455	Discontinued
0.6681	Remote Similarity	NPD3472	Approved
0.6681	Remote Similarity	NPD4022	Approved
0.6667	Remote Similarity	NPD7126	Discontinued
0.6651	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7278	Phase 2
0.6639	Remote Similarity	NPD7279	Phase 2
0.6638	Remote Similarity	NPD3888	Discontinued
0.6636	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5600	Discontinued
0.6626	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD3372	Discontinued
0.6623	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1945	Phase 1
0.6593	Remote Similarity	NPD7256	Discontinued
0.6589	Remote Similarity	NPD2249	Approved
0.6589	Remote Similarity	NPD2247	Approved
0.6584	Remote Similarity	NPD7186	Phase 3
0.6583	Remote Similarity	NPD3437	Discontinued
0.657	Remote Similarity	NPD7820	Phase 3
0.6568	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD7476	Discontinued
0.6565	Remote Similarity	NPD6321	Discontinued
0.6564	Remote Similarity	NPD5582	Discontinued
0.6559	Remote Similarity	NPD6723	Discontinued
0.6555	Remote Similarity	NPD8149	Discontinued
0.6546	Remote Similarity	NPD4846	Phase 2
0.6543	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD8489	Phase 1
0.6525	Remote Similarity	NPD7272	Discontinued
0.6514	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6107	Approved
0.6512	Remote Similarity	NPD6457	Approved
0.6507	Remote Similarity	NPD4420	Approved
0.6502	Remote Similarity	NPD3912	Discontinued
0.6502	Remote Similarity	NPD7542	Phase 3
0.6494	Remote Similarity	NPD7560	Approved
0.6491	Remote Similarity	NPD3964	Approved
0.6489	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7891	Discontinued
0.6466	Remote Similarity	NPD5005	Approved
0.6466	Remote Similarity	NPD5006	Approved
0.6462	Remote Similarity	NPD8461	Discontinued
0.6462	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7479	Phase 2
0.6444	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6716	Phase 1
0.6441	Remote Similarity	NPD8281	Discontinued
0.6435	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD3983	Phase 3
0.6423	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD2971	Approved
0.6413	Remote Similarity	NPD2968	Approved
0.641	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD5312	Approved
0.6409	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD8463	Approved
0.6409	Remote Similarity	NPD5313	Approved
0.6409	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD8027	Approved
0.6398	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5938	Phase 3
0.6393	Remote Similarity	NPD7940	Phase 3
0.6391	Remote Similarity	NPD7925	Phase 2
0.6391	Remote Similarity	NPD7924	Phase 2
0.6386	Remote Similarity	NPD4885	Approved
0.6383	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4500	Approved
0.6379	Remote Similarity	NPD4501	Approved
0.6376	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.636	Remote Similarity	NPD7827	Phase 1
0.6348	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD5997	Discontinued
0.6343	Remote Similarity	NPD7036	Phase 3
0.6343	Remote Similarity	NPD4796	Discontinued
0.6343	Remote Similarity	NPD7035	Approved
0.634	Remote Similarity	NPD4465	Phase 2
0.634	Remote Similarity	NPD4467	Phase 2
0.6336	Remote Similarity	NPD7810	Phase 3
0.6336	Remote Similarity	NPD7811	Phase 3
0.6332	Remote Similarity	NPD7262	Phase 1
0.6329	Remote Similarity	NPD4154	Approved
0.6328	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD8311	Discontinued
0.6327	Remote Similarity	NPD4515	Suspended
0.6327	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6997	Phase 2
0.632	Remote Similarity	NPD2975	Approved
0.632	Remote Similarity	NPD7796	Approved
0.632	Remote Similarity	NPD7797	Approved
0.632	Remote Similarity	NPD2974	Approved
0.632	Remote Similarity	NPD2973	Approved
0.6314	Remote Similarity	NPD6905	Phase 2
0.6313	Remote Similarity	NPD6037	Discontinued
0.6313	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6851	Approved
0.6311	Remote Similarity	NPD6853	Approved
0.6309	Remote Similarity	NPD4107	Approved
0.6309	Remote Similarity	NPD4580	Approved
0.6308	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4429	Discontinued
0.6296	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5482	Discontinued
0.629	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7994	Phase 2
0.6286	Remote Similarity	NPD7805	Phase 3
0.6285	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD6379	Discontinued
0.6274	Remote Similarity	NPD6357	Discontinued
0.6273	Remote Similarity	NPD2248	Approved
0.6273	Remote Similarity	NPD4481	Phase 3
0.6273	Remote Similarity	NPD2246	Approved
0.6273	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5496	Approved
0.6268	Remote Similarity	NPD1802	Approved
0.6268	Remote Similarity	NPD1801	Approved
0.6266	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7298	Approved
0.6256	Remote Similarity	NPD5847	Phase 1
0.625	Remote Similarity	NPD1743	Approved
0.625	Remote Similarity	NPD7223	Discontinued
0.625	Remote Similarity	NPD19	Approved
0.625	Remote Similarity	NPD5676	Approved
0.625	Remote Similarity	NPD7224	Discontinued
0.625	Remote Similarity	NPD1742	Approved
0.6245	Remote Similarity	NPD7668	Phase 2
0.624	Remote Similarity	NPD8100	Phase 3
0.6239	Remote Similarity	NPD3289	Phase 3
0.6239	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD3290	Approved
0.6239	Remote Similarity	NPD6519	Phase 2
0.6235	Remote Similarity	NPD8016	Phase 3
0.6235	Remote Similarity	NPD7885	Phase 2
0.6235	Remote Similarity	NPD7886	Phase 2

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