NPASS Compound

Structure

CID46225 OpenBabel06191715382D 38 42 0 0 1 0 0 0 0 0999 V2000 -5.7290 -0.6727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1944 -3.0995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3770 2.3815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3770 3.3815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9711 1.1942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5718 0.3948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0676 1.6229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5110 1.8815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5110 3.8815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9795 -1.6793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5875 -0.7593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4156 -1.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1061 2.8815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7323 -0.5922 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2024 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6944 -2.2335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6939 2.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6450 2.3815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6450 3.3815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7541 -2.3117 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6680 0.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7339 -2.5117 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6939 3.6905 0.0000 N 0 0 0 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 -1.3254 -3.2151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2806 0.5542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7741 -3.5109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 -0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 9 2 0 0 0 0 8 18 1 0 0 0 0 9 23 1 0 0 0 0 10 24 2 0 0 0 0 11 25 2 0 0 0 0 12 13 2 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 18 1 0 0 0 0 14 20 2 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 22 1 0 0 0 0 17 22 2 0 0 0 0 17 33 1 0 0 0 0 18 1 1 1 0 0 0 19 21 1 0 0 0 0 20 30 1 0 0 0 0 21 4 1 1 0 0 0 21 29 1 0 0 0 0 22 24 1 0 0 0 0 23 32 1 1 0 0 0 24 25 1 0 0 0 0 25 33 1 0 0 0 0 26 16 1 6 0 0 0 26 29 1 0 0 0 0 26 34 1 0 0 0 0 27 30 1 0 0 0 0 27 35 1 6 0 0 0 28 36 2 0 0 0 0 29 32 1 1 0 0 0 30 37 1 6 0 0 0 31 32 1 0 0 0 0 31 34 2 0 0 0 0 31 38 1 0 0 0 0 32 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.28
Volume:	550.036
LogP:	4.823
LogD:	4.29
LogS:	-4.828
# Rotatable Bonds:	2
TPSA:	96.1
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	5.765
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.878
MDCK Permeability:	1.8736023776000366e-05
Pgp-inhibitor:	0.962
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.906
Plasma Protein Binding (PPB):	99.13904571533203%
Volume Distribution (VD):	0.387
Pgp-substrate:	1.8906798362731934%

ADMET: Metabolism

CYP1A2-inhibitor:	0.292
CYP1A2-substrate:	0.459
CYP2C19-inhibitor:	0.949
CYP2C19-substrate:	0.643
CYP2C9-inhibitor:	0.868
CYP2C9-substrate:	0.602
CYP2D6-inhibitor:	0.473
CYP2D6-substrate:	0.695
CYP3A4-inhibitor:	0.972
CYP3A4-substrate:	0.306

ADMET: Excretion

Clearance (CL):	8.393
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.125
Human Hepatotoxicity (H-HT):	0.119
Drug-inuced Liver Injury (DILI):	0.229
AMES Toxicity:	0.344
Rat Oral Acute Toxicity:	0.891
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.505
Carcinogencity:	0.559
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC46225

Natural Product ID:	NPC46225
*Common Name:**	Cytoglobosin D
IUPAC Name:	n.a.
Synonyms:	Cytoglobosin D
Standard InCHIKey:	PSEVHIVYAHBJDR-HMIIDTQCSA-N
Standard InCHI:	InChI=1S/C32H38N2O4/c1-18-8-7-9-23-15-19(2)21(4)29-26(16-22-17-33-25-11-6-5-10-24(22)25)34-31(38)32(23,29)28(36)13-12-27(35)30(37)20(3)14-18/h5-7,9-15,17-18,21,23,26-27,29-30,33,35,37H,8,16H2,1-4H3,(H,34,38)/b9-7+,13-12+,20-14+/t18-,21+,23-,26-,27-,29-,30+,32+/m0/s1
SMILES:	C[C@H]1C/C=C/[C@H]2C=C(C)[C@H]([C@@H]3[C@]2(C(=N[C@H]3Cc2c[nH]c3c2cccc3)O)C(=O)/C=C/[C@@H]([C@@H](/C(=C/1)/C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098275
PubChem CID:	46209919
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001819] Isoindoles and derivatives [CHEMONTID:0002496] Isoindolines [CHEMONTID:0001820] Isoindolones

*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
NPO997	Peltodon longipes	Species	Lamiaceae	Eukaryota	roots	Santa Maria, South Brazil	2007-Dec	PMID[21775156]
NPO2853	Eschweilera coriacea	Species	Lecythidaceae	Eukaryota	bark	Suriname rainforest	n.a.	PMID[9677272]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3809	Eucalyptus cladocalyx	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO997	Peltodon longipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3809	Eucalyptus cladocalyx	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23741	Aspergillus violaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1920	Podocarpus elongata	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6621	Salvadora persica	Species	Salvadoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2853	Eschweilera coriacea	Species	Lecythidaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2550.0	nM	PMID[507688]

☑ 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 NPC46225 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	267
0.1-0.2	1322
0.2-0.3	6959
0.3-0.4	22084
0.4-0.5	7191
0.5-0.6	2371
0.6-0.7	1900
0.7-0.8	562
0.8-0.85	16
0.85-0.9	3
0.9-0.95	12
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9946	High Similarity	NPC127677
0.9836	High Similarity	NPC98715
0.9784	High Similarity	NPC225821
0.9734	High Similarity	NPC151976
0.9731	High Similarity	NPC258062
0.9526	High Similarity	NPC87856
0.9479	High Similarity	NPC204491
0.9476	High Similarity	NPC267965
0.9471	High Similarity	NPC271862
0.9399	High Similarity	NPC195239
0.9399	High Similarity	NPC157828
0.9378	High Similarity	NPC132211
0.9348	High Similarity	NPC11445
0.9278	High Similarity	NPC203614
0.9202	High Similarity	NPC300183
0.9141	High Similarity	NPC2395
0.91	High Similarity	NPC141428
0.8911	High Similarity	NPC235885
0.8824	High Similarity	NPC57690
0.8768	High Similarity	NPC147446
0.8592	High Similarity	NPC267926
0.8585	High Similarity	NPC266192
0.829	Intermediate Similarity	NPC47190
0.8255	Intermediate Similarity	NPC290529
0.8235	Intermediate Similarity	NPC151939
0.8191	Intermediate Similarity	NPC213468
0.8154	Intermediate Similarity	NPC267343
0.8108	Intermediate Similarity	NPC201700
0.809	Intermediate Similarity	NPC252338
0.8073	Intermediate Similarity	NPC280290
0.8053	Intermediate Similarity	NPC300688
0.8043	Intermediate Similarity	NPC311276
0.8043	Intermediate Similarity	NPC40779
0.8009	Intermediate Similarity	NPC70155
0.8	Intermediate Similarity	NPC154339
0.799	Intermediate Similarity	NPC131887
0.799	Intermediate Similarity	NPC477041
0.799	Intermediate Similarity	NPC477044
0.794	Intermediate Similarity	NPC227582
0.7938	Intermediate Similarity	NPC315555
0.7923	Intermediate Similarity	NPC469762
0.7921	Intermediate Similarity	NPC476874
0.7871	Intermediate Similarity	NPC475506
0.7869	Intermediate Similarity	NPC469785
0.7861	Intermediate Similarity	NPC477045
0.7857	Intermediate Similarity	NPC472285
0.785	Intermediate Similarity	NPC476818
0.7843	Intermediate Similarity	NPC477043
0.7833	Intermediate Similarity	NPC155143
0.7833	Intermediate Similarity	NPC260900
0.782	Intermediate Similarity	NPC473310
0.7814	Intermediate Similarity	NPC211572
0.7814	Intermediate Similarity	NPC212376
0.7814	Intermediate Similarity	NPC70922
0.7814	Intermediate Similarity	NPC80597
0.7814	Intermediate Similarity	NPC75540
0.7812	Intermediate Similarity	NPC270009
0.7806	Intermediate Similarity	NPC278434
0.7795	Intermediate Similarity	NPC163421
0.7795	Intermediate Similarity	NPC188387
0.7789	Intermediate Similarity	NPC313791
0.7778	Intermediate Similarity	NPC162860
0.7778	Intermediate Similarity	NPC476491
0.7772	Intermediate Similarity	NPC74413
0.7766	Intermediate Similarity	NPC160105
0.776	Intermediate Similarity	NPC259644
0.776	Intermediate Similarity	NPC25008
0.776	Intermediate Similarity	NPC73952
0.776	Intermediate Similarity	NPC469760
0.776	Intermediate Similarity	NPC469765
0.776	Intermediate Similarity	NPC469763
0.776	Intermediate Similarity	NPC469786
0.7755	Intermediate Similarity	NPC235684
0.7754	Intermediate Similarity	NPC102423
0.7737	Intermediate Similarity	NPC6982
0.7737	Intermediate Similarity	NPC470498
0.7734	Intermediate Similarity	NPC470497
0.7727	Intermediate Similarity	NPC95783
0.7727	Intermediate Similarity	NPC206967
0.7723	Intermediate Similarity	NPC473640
0.772	Intermediate Similarity	NPC176199
0.772	Intermediate Similarity	NPC215795
0.772	Intermediate Similarity	NPC472443
0.7708	Intermediate Similarity	NPC267885
0.77	Intermediate Similarity	NPC474177
0.7696	Intermediate Similarity	NPC314603
0.7696	Intermediate Similarity	NPC34508
0.7692	Intermediate Similarity	NPC107077
0.7692	Intermediate Similarity	NPC469358
0.7692	Intermediate Similarity	NPC472444
0.7692	Intermediate Similarity	NPC223791
0.7681	Intermediate Similarity	NPC54420
0.7677	Intermediate Similarity	NPC209917
0.7672	Intermediate Similarity	NPC474561
0.7672	Intermediate Similarity	NPC49954
0.7668	Intermediate Similarity	NPC111275
0.7665	Intermediate Similarity	NPC94752
0.7662	Intermediate Similarity	NPC133366
0.7659	Intermediate Similarity	NPC123019
0.7656	Intermediate Similarity	NPC203468
0.7656	Intermediate Similarity	NPC110500
0.7656	Intermediate Similarity	NPC149155
0.7653	Intermediate Similarity	NPC228835
0.765	Intermediate Similarity	NPC24678
0.765	Intermediate Similarity	NPC105818
0.7647	Intermediate Similarity	NPC131718
0.7641	Intermediate Similarity	NPC71037
0.7635	Intermediate Similarity	NPC265576
0.7632	Intermediate Similarity	NPC78020
0.763	Intermediate Similarity	NPC229348
0.7629	Intermediate Similarity	NPC248041
0.7629	Intermediate Similarity	NPC283219
0.7629	Intermediate Similarity	NPC126709
0.7629	Intermediate Similarity	NPC55772
0.7608	Intermediate Similarity	NPC478158
0.76	Intermediate Similarity	NPC138370
0.7598	Intermediate Similarity	NPC100321
0.7596	Intermediate Similarity	NPC88008
0.7594	Intermediate Similarity	NPC313640
0.7594	Intermediate Similarity	NPC230869
0.7594	Intermediate Similarity	NPC471284
0.7594	Intermediate Similarity	NPC474412
0.759	Intermediate Similarity	NPC477042
0.7588	Intermediate Similarity	NPC321708
0.7588	Intermediate Similarity	NPC213629
0.7583	Intermediate Similarity	NPC235900
0.7579	Intermediate Similarity	NPC54988
0.7577	Intermediate Similarity	NPC68354
0.7576	Intermediate Similarity	NPC99428
0.7574	Intermediate Similarity	NPC202812
0.7573	Intermediate Similarity	NPC193761
0.7573	Intermediate Similarity	NPC476073
0.7565	Intermediate Similarity	NPC275305
0.7565	Intermediate Similarity	NPC472586
0.7565	Intermediate Similarity	NPC37423
0.756	Intermediate Similarity	NPC314957
0.7555	Intermediate Similarity	NPC476516
0.755	Intermediate Similarity	NPC83111
0.7549	Intermediate Similarity	NPC470499
0.7549	Intermediate Similarity	NPC67288
0.7539	Intermediate Similarity	NPC154293
0.7538	Intermediate Similarity	NPC317030
0.7536	Intermediate Similarity	NPC320968
0.7523	Intermediate Similarity	NPC96131
0.7513	Intermediate Similarity	NPC282231
0.7512	Intermediate Similarity	NPC478157
0.75	Intermediate Similarity	NPC46413
0.75	Intermediate Similarity	NPC65215
0.75	Intermediate Similarity	NPC219087
0.75	Intermediate Similarity	NPC198339
0.75	Intermediate Similarity	NPC173028
0.75	Intermediate Similarity	NPC207020
0.7489	Intermediate Similarity	NPC472762
0.7488	Intermediate Similarity	NPC281049
0.7488	Intermediate Similarity	NPC234999
0.7487	Intermediate Similarity	NPC14113
0.7487	Intermediate Similarity	NPC293472
0.7487	Intermediate Similarity	NPC284775
0.7487	Intermediate Similarity	NPC145885
0.7487	Intermediate Similarity	NPC84827
0.7477	Intermediate Similarity	NPC89987
0.7474	Intermediate Similarity	NPC194640
0.7474	Intermediate Similarity	NPC293216
0.7464	Intermediate Similarity	NPC475288
0.7463	Intermediate Similarity	NPC171317
0.7463	Intermediate Similarity	NPC473747
0.7462	Intermediate Similarity	NPC192270
0.7462	Intermediate Similarity	NPC233936
0.746	Intermediate Similarity	NPC279918
0.745	Intermediate Similarity	NPC204565
0.745	Intermediate Similarity	NPC17059
0.7449	Intermediate Similarity	NPC11126
0.7448	Intermediate Similarity	NPC63751
0.7441	Intermediate Similarity	NPC284102
0.7435	Intermediate Similarity	NPC42372
0.7433	Intermediate Similarity	NPC470507
0.7432	Intermediate Similarity	NPC314372
0.7432	Intermediate Similarity	NPC159856
0.7427	Intermediate Similarity	NPC293917
0.7427	Intermediate Similarity	NPC32200
0.7426	Intermediate Similarity	NPC117244
0.7426	Intermediate Similarity	NPC473763
0.7424	Intermediate Similarity	NPC19679
0.7419	Intermediate Similarity	NPC276657
0.7418	Intermediate Similarity	NPC75634
0.7415	Intermediate Similarity	NPC229332
0.7413	Intermediate Similarity	NPC175474
0.7411	Intermediate Similarity	NPC471997
0.7409	Intermediate Similarity	NPC319232
0.7409	Intermediate Similarity	NPC194411
0.7409	Intermediate Similarity	NPC24370
0.7407	Intermediate Similarity	NPC264285
0.7407	Intermediate Similarity	NPC92796
0.7407	Intermediate Similarity	NPC477714
0.7407	Intermediate Similarity	NPC135141
0.7404	Intermediate Similarity	NPC328318
0.7404	Intermediate Similarity	NPC328596
0.7402	Intermediate Similarity	NPC85066
0.7402	Intermediate Similarity	NPC181502
0.74	Intermediate Similarity	NPC474707

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 NPC46225 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	500
0.2-0.3	662
0.3-0.4	1781
0.4-0.5	2855
0.5-0.6	2229
0.6-0.7	821
0.7-0.8	126
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7969	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD2091	Phase 2
0.7835	Intermediate Similarity	NPD2096	Phase 2
0.7816	Intermediate Similarity	NPD2510	Approved
0.7816	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD2509	Approved
0.7805	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD2092	Phase 2
0.7784	Intermediate Similarity	NPD2094	Phase 2
0.7784	Intermediate Similarity	NPD2095	Phase 2
0.7714	Intermediate Similarity	NPD8094	Discontinued
0.7668	Intermediate Similarity	NPD2144	Approved
0.7667	Intermediate Similarity	NPD8093	Discontinued
0.7656	Intermediate Similarity	NPD482	Approved
0.7653	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD3038	Discontinued
0.7629	Intermediate Similarity	NPD4076	Approved
0.7629	Intermediate Similarity	NPD4079	Approved
0.7619	Intermediate Similarity	NPD7470	Discontinued
0.7617	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7585	Intermediate Similarity	NPD5901	Discontinued
0.7585	Intermediate Similarity	NPD5426	Phase 3
0.7577	Intermediate Similarity	NPD3505	Approved
0.7577	Intermediate Similarity	NPD3506	Approved
0.7571	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD5065	Approved
0.7559	Intermediate Similarity	NPD3393	Approved
0.7559	Intermediate Similarity	NPD3389	Approved
0.7559	Intermediate Similarity	NPD3394	Approved
0.7548	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7957	Phase 1
0.7548	Intermediate Similarity	NPD7001	Phase 3
0.7539	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD8431	Approved
0.7536	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD6999	Discontinued
0.7512	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6595	Phase 3
0.7488	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD750	Phase 2
0.7407	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD7944	Discontinued
0.7391	Intermediate Similarity	NPD4600	Approved
0.7391	Intermediate Similarity	NPD4601	Approved
0.7391	Intermediate Similarity	NPD484	Approved
0.7371	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8072	Approved
0.7358	Intermediate Similarity	NPD2844	Phase 3
0.7333	Intermediate Similarity	NPD8272	Phase 2
0.733	Intermediate Similarity	NPD7948	Phase 1
0.733	Intermediate Similarity	NPD6664	Approved
0.7327	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD5897	Approved
0.7323	Intermediate Similarity	NPD5898	Approved
0.7323	Intermediate Similarity	NPD5899	Approved
0.7317	Intermediate Similarity	NPD7618	Phase 3
0.7317	Intermediate Similarity	NPD7619	Phase 3
0.7311	Intermediate Similarity	NPD8399	Phase 1
0.7311	Intermediate Similarity	NPD7666	Phase 3
0.7311	Intermediate Similarity	NPD8423	Phase 2
0.7311	Intermediate Similarity	NPD7665	Phase 2
0.7281	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD8326	Phase 3
0.7281	Intermediate Similarity	NPD8325	Phase 3
0.7277	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6987	Phase 1
0.725	Intermediate Similarity	NPD5596	Phase 2
0.7241	Intermediate Similarity	NPD7233	Approved
0.7241	Intermediate Similarity	NPD7234	Approved
0.7238	Intermediate Similarity	NPD8073	Approved
0.7228	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3794	Approved
0.7222	Intermediate Similarity	NPD3795	Approved
0.7222	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD53	Approved
0.7212	Intermediate Similarity	NPD7778	Approved
0.7212	Intermediate Similarity	NPD7777	Approved
0.7209	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3871	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3870	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3178	Discontinued
0.7198	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6242	Discontinued
0.7181	Intermediate Similarity	NPD4462	Approved
0.7181	Intermediate Similarity	NPD2172	Phase 1
0.7181	Intermediate Similarity	NPD4463	Approved
0.7179	Intermediate Similarity	NPD4640	Approved
0.7179	Intermediate Similarity	NPD4639	Approved
0.7179	Intermediate Similarity	NPD4638	Approved
0.7178	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1592	Phase 3
0.7172	Intermediate Similarity	NPD4075	Phase 2
0.7171	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD56	Approved
0.717	Intermediate Similarity	NPD8283	Approved
0.717	Intermediate Similarity	NPD8282	Approved
0.7165	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5003	Discontinued
0.7158	Intermediate Similarity	NPD786	Approved
0.7143	Intermediate Similarity	NPD6164	Phase 2
0.7143	Intermediate Similarity	NPD1325	Approved
0.7143	Intermediate Similarity	NPD1326	Approved
0.7143	Intermediate Similarity	NPD6165	Phase 2
0.7124	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6176	Phase 1
0.7122	Intermediate Similarity	NPD4499	Approved
0.7113	Intermediate Similarity	NPD5138	Approved
0.7113	Intermediate Similarity	NPD5088	Discontinued
0.7113	Intermediate Similarity	NPD5140	Approved
0.7101	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD8289	Discontinued
0.7098	Intermediate Similarity	NPD2511	Approved
0.7097	Intermediate Similarity	NPD4852	Phase 2
0.7095	Intermediate Similarity	NPD6248	Phase 2
0.7095	Intermediate Similarity	NPD6249	Phase 2
0.7095	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7878	Phase 2
0.7083	Intermediate Similarity	NPD4051	Discontinued
0.7081	Intermediate Similarity	NPD1722	Approved
0.708	Intermediate Similarity	NPD7824	Approved
0.7074	Intermediate Similarity	NPD4702	Approved
0.7074	Intermediate Similarity	NPD4703	Approved
0.7065	Intermediate Similarity	NPD5473	Discontinued
0.7051	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD8123	Approved
0.705	Intermediate Similarity	NPD4181	Approved
0.705	Intermediate Similarity	NPD8122	Approved
0.7039	Intermediate Similarity	NPD2564	Approved
0.7039	Intermediate Similarity	NPD2565	Phase 2
0.7037	Intermediate Similarity	NPD3100	Discontinued
0.7035	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3323	Discontinued
0.7024	Intermediate Similarity	NPD3961	Discontinued
0.7022	Intermediate Similarity	NPD7603	Discontinued
0.7019	Intermediate Similarity	NPD1038	Approved
0.7009	Intermediate Similarity	NPD8114	Approved
0.7009	Intermediate Similarity	NPD3947	Discontinued
0.7009	Intermediate Similarity	NPD8115	Approved
0.7009	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD2336	Approved
0.7	Intermediate Similarity	NPD5612	Discontinued
0.7	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2380	Approved
0.7	Intermediate Similarity	NPD2381	Approved
0.7	Intermediate Similarity	NPD2382	Approved
0.6995	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7187	Phase 2
0.6991	Remote Similarity	NPD7731	Approved
0.6991	Remote Similarity	NPD7730	Approved
0.699	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7952	Approved
0.6987	Remote Similarity	NPD7950	Approved
0.6987	Remote Similarity	NPD7790	Approved
0.6987	Remote Similarity	NPD7953	Approved
0.6987	Remote Similarity	NPD7789	Approved
0.6987	Remote Similarity	NPD7951	Approved
0.6987	Remote Similarity	NPD7791	Approved
0.6986	Remote Similarity	NPD4427	Phase 2
0.6981	Remote Similarity	NPD6479	Discontinued
0.6981	Remote Similarity	NPD4500	Approved
0.6981	Remote Similarity	NPD4501	Approved
0.698	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5067	Phase 2
0.6972	Remote Similarity	NPD5066	Phase 2
0.6968	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5487	Phase 1
0.6961	Remote Similarity	NPD7564	Discontinued
0.6961	Remote Similarity	NPD6178	Phase 3
0.696	Remote Similarity	NPD7781	Approved
0.696	Remote Similarity	NPD7780	Approved
0.6957	Remote Similarity	NPD6281	Approved
0.6955	Remote Similarity	NPD7707	Approved
0.695	Remote Similarity	NPD4128	Approved
0.6948	Remote Similarity	NPD7817	Phase 1
0.6944	Remote Similarity	NPD8322	Phase 2
0.6944	Remote Similarity	NPD1392	Approved
0.6943	Remote Similarity	NPD6026	Approved
0.6942	Remote Similarity	NPD4948	Discontinued
0.6938	Remote Similarity	NPD802	Phase 2
0.6931	Remote Similarity	NPD8386	Phase 2
0.693	Remote Similarity	NPD8098	Approved
0.6915	Remote Similarity	NPD5100	Phase 3
0.6912	Remote Similarity	NPD3319	Phase 1
0.6912	Remote Similarity	NPD3320	Approved
0.6912	Remote Similarity	NPD3318	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