NPASS Compound

Structure

NPC470936 OpenBabel07101719522D 47 51 0 0 1 0 0 0 0 0999 V2000 1.4144 -7.5638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3490 -2.4421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6222 -1.0298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0112 2.9679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5644 1.6080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2339 0.6857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9308 2.3554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6458 -4.2299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1815 -3.3671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2698 0.5107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9668 2.1805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3770 0.3203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6739 -1.2242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2687 -0.0857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5656 -1.6302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0800 -6.7597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1308 -5.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6966 -2.5336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5443 -7.6225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7736 1.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1626 0.0871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8994 -6.7304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6363 1.2581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5796 -0.2490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3630 -1.0609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7736 0.4399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1626 1.4982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5516 0.4399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7082 0.9082 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5516 1.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2831 0.0255 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3636 -5.8676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7474 -0.8373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8628 1.1210 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 1.5853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6879 0.1570 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8486 -5.0341 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2323 -1.6708 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5236 -7.6518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3430 -5.8382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7267 -0.8666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7456 1.5462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2386 2.5356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2548 -1.4669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6222 -0.0500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1626 2.4780 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 22 1 0 0 0 0 2 44 1 0 0 0 0 3 45 1 0 0 0 0 4 46 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 23 2 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 24 2 0 0 0 0 13 15 2 0 0 0 0 13 24 1 0 0 0 0 14 25 2 0 0 0 0 15 25 1 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 37 1 0 0 0 0 18 38 1 0 0 0 0 19 39 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 21 28 2 0 0 0 0 22 32 1 0 0 0 0 23 29 1 0 0 0 0 25 44 1 0 0 0 0 26 45 1 0 0 0 0 27 30 2 0 0 0 0 27 46 1 0 0 0 0 28 30 1 0 0 0 0 28 47 1 0 0 0 0 29 31 1 0 0 0 0 29 35 1 6 0 0 0 30 35 1 0 0 0 0 31 33 1 0 0 0 0 31 36 1 1 0 0 0 32 37 2 3 0 0 0 32 40 1 0 0 0 0 33 38 2 3 0 0 0 33 41 1 0 0 0 0 34 35 1 0 0 0 0 34 36 1 0 0 0 0 34 42 1 0 0 0 0 35 43 1 1 0 0 0 36 24 1 1 0 0 0 36 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	646.29
Volume:	657.898
LogP:	2.766
LogD:	2.82
LogS:	-4.274
# Rotatable Bonds:	16
TPSA:	152.65
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.153
Synthetic Accessibility Score:	5.228
Fsp3:	0.417
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.414
MDCK Permeability:	1.2299531590542756e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.684
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.349
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.882
Plasma Protein Binding (PPB):	87.81395721435547%
Volume Distribution (VD):	2.105
Pgp-substrate:	4.2614312171936035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.33
CYP2C19-inhibitor:	0.175
CYP2C19-substrate:	0.861
CYP2C9-inhibitor:	0.192
CYP2C9-substrate:	0.15
CYP2D6-inhibitor:	0.935
CYP2D6-substrate:	0.779
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.795

ADMET: Excretion

Clearance (CL):	7.993
Half-life (T1/2):	0.06

ADMET: Toxicity

hERG Blockers:	0.157
Human Hepatotoxicity (H-HT):	0.749
Drug-inuced Liver Injury (DILI):	0.286
AMES Toxicity:	0.158
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.435
Skin Sensitization:	0.051
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.437

Download Data

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

Natural Product: NPC470936

Natural Product ID:	NPC470936
*Common Name:**	ZPZIOXSKRNWLQT-YFLBEWKFSA-N
IUPAC Name:	n.a.
Synonyms:	Perviridisin A; Perviridisin B
Standard InCHIKey:	ZPZIOXSKRNWLQT-YFLBEWKFSA-N
Standard InCHI:	InChI=1S/C36H42N2O9/c1-22(16-19-39)32(40)37-17-8-9-18-38-33(41)31-29(23-10-6-5-7-11-23)35(43)30-27(46-4)20-26(45-3)21-28(30)47-36(31,34(35)42)24-12-14-25(44-2)15-13-24/h5-7,10-16,20-21,29,31,34,39,42-43H,8-9,17-19H2,1-4H3,(H,37,40)(H,38,41)/b22-16+/t29-,31+,34?,35-,36+/m0/s1
SMILES:	CC(=CCO)C(=O)NCCCCNC(=O)C1C(C2(C(C1(OC3=C2C(=CC(=C3)OC)OC)C4=CC=C(C=C4)OC)O)O)C5=CC=CC=C5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2331814
PubChem CID:	71664735
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	leaves, twigs, and fruits	Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam	2010-Jan	PMID[23301897]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31621322]
NPO4720	Aglaia perviridis	Species	Meliaceae	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	5

Activity Type	# Activity
Cell Line	2
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	uM	PMID[464148]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.46	uM	PMID[464147]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	ED50	=	2.4	uM	PMID[464147]
NPT27	Others	Unspecified		ED50	>	50.0	uM	PMID[464147]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	ED50	>	20.0	uM	PMID[464148]

☑ 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 NPC470936 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	252
0.1-0.2	1278
0.2-0.3	3482
0.3-0.4	11109
0.4-0.5	8233
0.5-0.6	8760
0.6-0.7	8512
0.7-0.8	1049
0.8-0.85	16
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC87363
0.8974	High Similarity	NPC51543
0.8636	High Similarity	NPC184607
0.8571	High Similarity	NPC470937
0.8303	Intermediate Similarity	NPC179250
0.8303	Intermediate Similarity	NPC50380
0.8302	Intermediate Similarity	NPC20360
0.8263	Intermediate Similarity	NPC90984
0.8207	Intermediate Similarity	NPC79130
0.8118	Intermediate Similarity	NPC475621
0.8056	Intermediate Similarity	NPC308709
0.8025	Intermediate Similarity	NPC475836
0.8021	Intermediate Similarity	NPC293347
0.8	Intermediate Similarity	NPC475492
0.7964	Intermediate Similarity	NPC189730
0.7963	Intermediate Similarity	NPC471032
0.7963	Intermediate Similarity	NPC470935
0.795	Intermediate Similarity	NPC181615
0.7931	Intermediate Similarity	NPC254071
0.7931	Intermediate Similarity	NPC149502
0.7931	Intermediate Similarity	NPC222665
0.7931	Intermediate Similarity	NPC271755
0.7929	Intermediate Similarity	NPC310399
0.7929	Intermediate Similarity	NPC73422
0.7927	Intermediate Similarity	NPC127402
0.7925	Intermediate Similarity	NPC100482
0.7925	Intermediate Similarity	NPC178054
0.7925	Intermediate Similarity	NPC277331
0.7922	Intermediate Similarity	NPC162801
0.7904	Intermediate Similarity	NPC164152
0.7901	Intermediate Similarity	NPC211758
0.7901	Intermediate Similarity	NPC87794
0.7898	Intermediate Similarity	NPC18189
0.7898	Intermediate Similarity	NPC262585
0.7898	Intermediate Similarity	NPC20829
0.7892	Intermediate Similarity	NPC107602
0.7888	Intermediate Similarity	NPC313414
0.7885	Intermediate Similarity	NPC117048
0.7885	Intermediate Similarity	NPC124085
0.787	Intermediate Similarity	NPC209473
0.787	Intermediate Similarity	NPC329743
0.7853	Intermediate Similarity	NPC327412
0.7853	Intermediate Similarity	NPC320970
0.7853	Intermediate Similarity	NPC320671
0.7853	Intermediate Similarity	NPC328567
0.7853	Intermediate Similarity	NPC206061
0.7848	Intermediate Similarity	NPC474687
0.7848	Intermediate Similarity	NPC470307
0.7848	Intermediate Similarity	NPC470308
0.7843	Intermediate Similarity	NPC87224
0.7843	Intermediate Similarity	NPC222572
0.7826	Intermediate Similarity	NPC274721
0.7826	Intermediate Similarity	NPC135767
0.7826	Intermediate Similarity	NPC155392
0.7821	Intermediate Similarity	NPC92805
0.7821	Intermediate Similarity	NPC85435
0.7818	Intermediate Similarity	NPC477612
0.7812	Intermediate Similarity	NPC108674
0.7812	Intermediate Similarity	NPC476334
0.7806	Intermediate Similarity	NPC103799
0.7805	Intermediate Similarity	NPC114659
0.7805	Intermediate Similarity	NPC139699
0.7791	Intermediate Similarity	NPC317053
0.7791	Intermediate Similarity	NPC260397
0.7791	Intermediate Similarity	NPC324492
0.7785	Intermediate Similarity	NPC471522
0.7785	Intermediate Similarity	NPC3049
0.7778	Intermediate Similarity	NPC277951
0.7778	Intermediate Similarity	NPC90336
0.7778	Intermediate Similarity	NPC44530
0.7778	Intermediate Similarity	NPC317237
0.7771	Intermediate Similarity	NPC324517
0.7771	Intermediate Similarity	NPC223008
0.7771	Intermediate Similarity	NPC476615
0.7771	Intermediate Similarity	NPC321972
0.7771	Intermediate Similarity	NPC296915
0.7771	Intermediate Similarity	NPC115335
0.7771	Intermediate Similarity	NPC476616
0.7771	Intermediate Similarity	NPC198154
0.7771	Intermediate Similarity	NPC97834
0.7771	Intermediate Similarity	NPC476617
0.7771	Intermediate Similarity	NPC225696
0.7771	Intermediate Similarity	NPC329343
0.7764	Intermediate Similarity	NPC472353
0.7756	Intermediate Similarity	NPC13005
0.775	Intermediate Similarity	NPC266197
0.775	Intermediate Similarity	NPC291101
0.7727	Intermediate Similarity	NPC39064
0.7727	Intermediate Similarity	NPC47283
0.7725	Intermediate Similarity	NPC59692
0.7725	Intermediate Similarity	NPC233467
0.7712	Intermediate Similarity	NPC230479
0.7712	Intermediate Similarity	NPC26879
0.7712	Intermediate Similarity	NPC283049
0.7712	Intermediate Similarity	NPC50315
0.7711	Intermediate Similarity	NPC474560
0.7697	Intermediate Similarity	NPC315913
0.7697	Intermediate Similarity	NPC227516
0.7697	Intermediate Similarity	NPC20757
0.7692	Intermediate Similarity	NPC236014
0.7692	Intermediate Similarity	NPC207892
0.7692	Intermediate Similarity	NPC118683
0.7692	Intermediate Similarity	NPC12875
0.7692	Intermediate Similarity	NPC228369
0.7692	Intermediate Similarity	NPC271945
0.7692	Intermediate Similarity	NPC129784
0.7692	Intermediate Similarity	NPC211413
0.7692	Intermediate Similarity	NPC129106
0.7692	Intermediate Similarity	NPC476166
0.7692	Intermediate Similarity	NPC300875
0.7692	Intermediate Similarity	NPC268917
0.7692	Intermediate Similarity	NPC164574
0.7692	Intermediate Similarity	NPC196765
0.7692	Intermediate Similarity	NPC118114
0.7692	Intermediate Similarity	NPC17343
0.7692	Intermediate Similarity	NPC206224
0.7692	Intermediate Similarity	NPC181497
0.7692	Intermediate Similarity	NPC68205
0.7692	Intermediate Similarity	NPC244888
0.7692	Intermediate Similarity	NPC293203
0.7692	Intermediate Similarity	NPC150011
0.7692	Intermediate Similarity	NPC280653
0.7692	Intermediate Similarity	NPC164804
0.7683	Intermediate Similarity	NPC248053
0.7683	Intermediate Similarity	NPC155564
0.7683	Intermediate Similarity	NPC102280
0.7677	Intermediate Similarity	NPC93962
0.7669	Intermediate Similarity	NPC114119
0.7669	Intermediate Similarity	NPC470097
0.7669	Intermediate Similarity	NPC471415
0.7665	Intermediate Similarity	NPC471403
0.7665	Intermediate Similarity	NPC302915
0.7665	Intermediate Similarity	NPC259707
0.7654	Intermediate Similarity	NPC178466
0.7654	Intermediate Similarity	NPC63628
0.7651	Intermediate Similarity	NPC470098
0.7651	Intermediate Similarity	NPC211561
0.7651	Intermediate Similarity	NPC473266
0.7651	Intermediate Similarity	NPC470826
0.7647	Intermediate Similarity	NPC207179
0.7647	Intermediate Similarity	NPC278552
0.7647	Intermediate Similarity	NPC167571
0.764	Intermediate Similarity	NPC221134
0.764	Intermediate Similarity	NPC314213
0.764	Intermediate Similarity	NPC309124
0.764	Intermediate Similarity	NPC184797
0.764	Intermediate Similarity	NPC195814
0.7636	Intermediate Similarity	NPC263940
0.7636	Intermediate Similarity	NPC236202
0.7636	Intermediate Similarity	NPC170103
0.7636	Intermediate Similarity	NPC262911
0.7636	Intermediate Similarity	NPC18185
0.7636	Intermediate Similarity	NPC82917
0.7636	Intermediate Similarity	NPC58190
0.7636	Intermediate Similarity	NPC70409
0.7636	Intermediate Similarity	NPC294558
0.7636	Intermediate Similarity	NPC108811
0.7636	Intermediate Similarity	NPC202742
0.7636	Intermediate Similarity	NPC204770
0.7628	Intermediate Similarity	NPC470225
0.7628	Intermediate Similarity	NPC27187
0.7625	Intermediate Similarity	NPC262328
0.7625	Intermediate Similarity	NPC87777
0.7619	Intermediate Similarity	NPC187028
0.7619	Intermediate Similarity	NPC305700
0.7619	Intermediate Similarity	NPC226809
0.7619	Intermediate Similarity	NPC157783
0.7619	Intermediate Similarity	NPC197741
0.7619	Intermediate Similarity	NPC279406
0.7619	Intermediate Similarity	NPC18249
0.7619	Intermediate Similarity	NPC10221
0.7619	Intermediate Similarity	NPC140915
0.7613	Intermediate Similarity	NPC274717
0.7613	Intermediate Similarity	NPC38664
0.7613	Intermediate Similarity	NPC53986
0.761	Intermediate Similarity	NPC164787
0.761	Intermediate Similarity	NPC151224
0.761	Intermediate Similarity	NPC61946
0.761	Intermediate Similarity	NPC93783
0.7605	Intermediate Similarity	NPC158784
0.7597	Intermediate Similarity	NPC262573
0.7597	Intermediate Similarity	NPC471215
0.7595	Intermediate Similarity	NPC77196
0.7595	Intermediate Similarity	NPC215037
0.7595	Intermediate Similarity	NPC263064
0.7593	Intermediate Similarity	NPC5155
0.7593	Intermediate Similarity	NPC471389
0.759	Intermediate Similarity	NPC281549
0.7588	Intermediate Similarity	NPC475565
0.7588	Intermediate Similarity	NPC475292
0.7588	Intermediate Similarity	NPC475442
0.7588	Intermediate Similarity	NPC475349
0.7584	Intermediate Similarity	NPC314025
0.7582	Intermediate Similarity	NPC294156
0.7582	Intermediate Similarity	NPC256015
0.758	Intermediate Similarity	NPC472590
0.7578	Intermediate Similarity	NPC471388
0.7578	Intermediate Similarity	NPC232164
0.7578	Intermediate Similarity	NPC473739
0.7578	Intermediate Similarity	NPC260842

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 NPC470936 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	663
0.2-0.3	1072
0.3-0.4	2686
0.4-0.5	2415
0.5-0.6	1498
0.6-0.7	618
0.7-0.8	35
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
0.7843	Intermediate Similarity	NPD4908	Phase 1
0.7811	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7466	Approved
0.7742	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7447	Phase 1
0.7643	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7212	Phase 2
0.7622	Intermediate Similarity	NPD7213	Phase 3
0.7619	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6072	Discontinued
0.7421	Intermediate Similarity	NPD1613	Approved
0.7421	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1610	Phase 2
0.7358	Intermediate Similarity	NPD7477	Discontinued
0.7353	Intermediate Similarity	NPD4675	Approved
0.7353	Intermediate Similarity	NPD4678	Approved
0.7333	Intermediate Similarity	NPD6331	Phase 2
0.7329	Intermediate Similarity	NPD2157	Approved
0.7325	Intermediate Similarity	NPD2861	Phase 2
0.7225	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8070	Approved
0.7193	Intermediate Similarity	NPD4005	Discontinued
0.7193	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5735	Approved
0.7158	Intermediate Similarity	NPD7549	Discontinued
0.7126	Intermediate Similarity	NPD5773	Approved
0.7126	Intermediate Similarity	NPD7089	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5772	Approved
0.7125	Intermediate Similarity	NPD3027	Phase 3
0.7119	Intermediate Similarity	NPD6746	Phase 2
0.7118	Intermediate Similarity	NPD52	Approved
0.7118	Intermediate Similarity	NPD7526	Approved
0.7118	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2238	Phase 2
0.7091	Intermediate Similarity	NPD2161	Phase 2
0.7086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8053	Approved
0.7081	Intermediate Similarity	NPD8054	Approved
0.7081	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7199	Phase 2
0.7069	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4123	Phase 3
0.7049	Intermediate Similarity	NPD7007	Discovery
0.7048	Intermediate Similarity	NPD5762	Approved
0.7048	Intermediate Similarity	NPD5763	Approved
0.7024	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1548	Phase 1
0.7	Intermediate Similarity	NPD1712	Approved
0.6989	Remote Similarity	NPD2415	Discontinued
0.6978	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2122	Discontinued
0.6968	Remote Similarity	NPD7906	Approved
0.6962	Remote Similarity	NPD6583	Phase 3
0.6962	Remote Similarity	NPD6582	Phase 2
0.6962	Remote Similarity	NPD4749	Approved
0.6959	Remote Similarity	NPD7019	Approved
0.6959	Remote Similarity	NPD7020	Approved
0.6959	Remote Similarity	NPD3985	Discontinued
0.6959	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6502	Phase 2
0.6951	Remote Similarity	NPD5124	Phase 1
0.6951	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7773	Phase 2
0.6941	Remote Similarity	NPD6667	Approved
0.6941	Remote Similarity	NPD3122	Phase 3
0.6941	Remote Similarity	NPD6666	Approved
0.694	Remote Similarity	NPD8156	Discontinued
0.6937	Remote Similarity	NPD6584	Phase 3
0.6932	Remote Similarity	NPD5929	Approved
0.6932	Remote Similarity	NPD8455	Phase 2
0.6928	Remote Similarity	NPD4108	Discontinued
0.6918	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD8651	Approved
0.6914	Remote Similarity	NPD4625	Phase 3
0.6906	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2424	Discontinued
0.6885	Remote Similarity	NPD8252	Approved
0.6885	Remote Similarity	NPD8251	Approved
0.6885	Remote Similarity	NPD8099	Discontinued
0.6882	Remote Similarity	NPD2677	Approved
0.6878	Remote Similarity	NPD6842	Approved
0.6878	Remote Similarity	NPD6843	Phase 3
0.6878	Remote Similarity	NPD6841	Approved
0.6871	Remote Similarity	NPD1048	Approved
0.6868	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6166	Phase 2
0.6868	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2200	Suspended
0.6864	Remote Similarity	NPD5061	Approved
0.6864	Remote Similarity	NPD5177	Phase 3
0.6864	Remote Similarity	NPD5062	Approved
0.6864	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4380	Phase 2
0.6855	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3685	Discontinued
0.6854	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD3051	Approved
0.6848	Remote Similarity	NPD6355	Discontinued
0.6845	Remote Similarity	NPD1375	Discontinued
0.6845	Remote Similarity	NPD7030	Discontinued
0.6842	Remote Similarity	NPD7843	Approved
0.6842	Remote Similarity	NPD6815	Approved
0.6836	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1091	Approved
0.6829	Remote Similarity	NPD840	Approved
0.6829	Remote Similarity	NPD839	Approved
0.6826	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4663	Approved
0.6824	Remote Similarity	NPD3892	Phase 2
0.6821	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3778	Approved
0.6818	Remote Similarity	NPD7157	Approved
0.6816	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7831	Phase 2
0.6816	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4055	Discovery
0.6816	Remote Similarity	NPD7833	Phase 2
0.6813	Remote Similarity	NPD2970	Approved
0.6813	Remote Similarity	NPD2969	Approved
0.6807	Remote Similarity	NPD6653	Approved
0.6807	Remote Similarity	NPD4097	Suspended
0.6807	Remote Similarity	NPD6353	Approved
0.6805	Remote Similarity	NPD7037	Approved
0.6805	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6087	Phase 1
0.6802	Remote Similarity	NPD4357	Discontinued
0.6784	Remote Similarity	NPD2219	Phase 1
0.6782	Remote Similarity	NPD7801	Approved
0.678	Remote Similarity	NPD5722	Discontinued
0.678	Remote Similarity	NPD4433	Discontinued
0.6774	Remote Similarity	NPD3823	Discontinued
0.677	Remote Similarity	NPD3094	Phase 2
0.6768	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD8151	Discontinued
0.6766	Remote Similarity	NPD4538	Approved
0.6766	Remote Similarity	NPD4536	Approved
0.6766	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7097	Phase 1
0.6765	Remote Similarity	NPD6674	Discontinued
0.6765	Remote Similarity	NPD1652	Phase 2
0.6763	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6071	Discontinued
0.6758	Remote Similarity	NPD7315	Approved
0.6757	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7310	Approved
0.6755	Remote Similarity	NPD4578	Approved
0.6755	Remote Similarity	NPD7312	Approved
0.6755	Remote Similarity	NPD7311	Approved
0.6755	Remote Similarity	NPD7313	Approved
0.6755	Remote Similarity	NPD4577	Approved
0.6752	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5327	Phase 3
0.6746	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6002	Phase 3
0.6746	Remote Similarity	NPD6004	Phase 3
0.6746	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6005	Phase 3
0.6744	Remote Similarity	NPD7124	Phase 2
0.6744	Remote Similarity	NPD5058	Phase 3
0.6742	Remote Similarity	NPD7972	Discontinued
0.6738	Remote Similarity	NPD7685	Pre-registration
0.6727	Remote Similarity	NPD3162	Approved
0.6727	Remote Similarity	NPD3163	Approved
0.6727	Remote Similarity	NPD1423	Approved
0.6727	Remote Similarity	NPD7265	Discontinued
0.6726	Remote Similarity	NPD5588	Approved
0.6722	Remote Similarity	NPD7075	Discontinued
0.6722	Remote Similarity	NPD6971	Discontinued
0.672	Remote Similarity	NPD7309	Approved
0.6717	Remote Similarity	NPD6823	Phase 2
0.6709	Remote Similarity	NPD2668	Approved
0.6709	Remote Similarity	NPD2667	Approved
0.6705	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7228	Approved
0.6703	Remote Similarity	NPD8127	Discontinued
0.6702	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6580	Approved
0.6688	Remote Similarity	NPD6581	Approved
0.6688	Remote Similarity	NPD7741	Discontinued
0.6687	Remote Similarity	NPD2231	Phase 2
0.6687	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4993	Discontinued
0.6687	Remote Similarity	NPD2232	Approved
0.6687	Remote Similarity	NPD2233	Approved
0.6687	Remote Similarity	NPD4140	Approved
0.6687	Remote Similarity	NPD2230	Approved
0.6687	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3620	Phase 2
0.6687	Remote Similarity	NPD2235	Phase 2
0.6686	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3692	Discontinued
0.6685	Remote Similarity	NPD1934	Approved

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