NPASS Compound

Structure

CID151976 OpenBabel06191715522D 39 43 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 -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 -1.2024 4.0827 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 3.5110 1.8815 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 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 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 -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 0 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 1.6939 2.0725 0.0000 C 0 0 0 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 -2.0685 1.5827 0.0000 C 0 0 1 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 -2.0685 2.5827 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 -2.9345 3.0827 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 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 10 2 0 0 0 0 8 17 1 0 0 0 0 9 22 2 0 0 0 0 10 23 1 0 0 0 0 11 24 2 0 0 0 0 12 13 2 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 21 1 0 0 0 0 16 21 2 0 0 0 0 16 33 1 0 0 0 0 17 1 1 1 0 0 0 18 29 1 0 0 0 0 19 20 2 0 0 0 0 19 28 1 0 0 0 0 20 30 1 0 0 0 0 21 22 1 0 0 0 0 22 24 1 0 0 0 0 23 30 1 0 0 0 0 23 32 1 1 0 0 0 24 33 1 0 0 0 0 25 15 1 6 0 0 0 25 28 1 0 0 0 0 25 34 1 0 0 0 0 26 29 1 0 0 0 0 26 35 1 6 0 0 0 27 36 2 0 0 0 0 28 32 1 1 0 0 0 29 37 1 6 0 0 0 30 38 1 6 0 0 0 31 32 1 0 0 0 0 31 34 2 0 0 0 0 31 39 1 0 0 0 0 32 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.28
Volume:	558.826
LogP:	3.939
LogD:	3.717
LogS:	-4.513
# Rotatable Bonds:	2
TPSA:	116.33
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.305
Synthetic Accessibility Score:	5.735
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:	-4.988
MDCK Permeability:	1.1777898180298507e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.197

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	96.8673324584961%
Volume Distribution (VD):	0.4
Pgp-substrate:	2.5998167991638184%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.401
CYP2C19-inhibitor:	0.81
CYP2C19-substrate:	0.702
CYP2C9-inhibitor:	0.71
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.147
CYP2D6-substrate:	0.507
CYP3A4-inhibitor:	0.951
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	8.958
Half-life (T1/2):	0.338

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.754
Drug-inuced Liver Injury (DILI):	0.16
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.687
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.409
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.692

Download Data

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

Natural Product: NPC151976

Natural Product ID:	NPC151976
*Common Name:**	Cytoglobosin C
IUPAC Name:	n.a.
Synonyms:	Cytoglobosin C
Standard InCHIKey:	VWKVHGIGUCPWKR-HDCYGHGWSA-N
Standard InCHI:	InChI=1S/C32H38N2O5/c1-17-8-7-10-23-30(38)20(4)19(3)28-25(15-21-16-33-24-11-6-5-9-22(21)24)34-31(39)32(23,28)27(36)13-12-26(35)29(37)18(2)14-17/h5-7,9-14,16-17,23,25-26,28-30,33,35,37-38H,8,15H2,1-4H3,(H,34,39)/b10-7+,13-12+,18-14+/t17-,23-,25-,26-,28-,29+,30+,32+/m0/s1
SMILES:	C[C@H]1C/C=C/[C@H]2[C@H](O)C(=C([C@@H]3[C@@]2(C(=O)/C=C/[C@@H]([C@@H](/C(=C/1)/C)O)O)C(=N[C@H]3Cc1c[nH]c2c1cccc2)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097579
PubChem CID:	44610809
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]
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[TCMID]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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]
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]

☑ 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	=	2260.0	nM	PMID[508801]

☑ 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 NPC151976 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	276
0.1-0.2	1346
0.2-0.3	6978
0.3-0.4	22223
0.4-0.5	7004
0.5-0.6	2383
0.6-0.7	1912
0.7-0.8	535
0.8-0.85	13
0.85-0.9	4
0.9-0.95	12
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC87856
0.974	High Similarity	NPC204491
0.9738	High Similarity	NPC267965
0.9734	High Similarity	NPC46225
0.9683	High Similarity	NPC127677
0.9637	High Similarity	NPC132211
0.9574	High Similarity	NPC98715
0.9536	High Similarity	NPC203614
0.9526	High Similarity	NPC225821
0.9476	High Similarity	NPC258062
0.9427	High Similarity	NPC271862
0.9394	High Similarity	NPC2395
0.935	High Similarity	NPC141428
0.9158	High Similarity	NPC235885
0.9149	High Similarity	NPC157828
0.9149	High Similarity	NPC195239
0.9101	High Similarity	NPC11445
0.9069	High Similarity	NPC57690
0.9015	High Similarity	NPC147446
0.8964	High Similarity	NPC300183
0.8835	High Similarity	NPC267926
0.8829	High Similarity	NPC266192
0.8491	Intermediate Similarity	NPC290529
0.8157	Intermediate Similarity	NPC70155
0.8131	Intermediate Similarity	NPC267343
0.8081	Intermediate Similarity	NPC47190
0.8021	Intermediate Similarity	NPC151939
0.798	Intermediate Similarity	NPC154339
0.798	Intermediate Similarity	NPC252338
0.7979	Intermediate Similarity	NPC213468
0.797	Intermediate Similarity	NPC131887
0.7938	Intermediate Similarity	NPC300688
0.7919	Intermediate Similarity	NPC315555
0.7895	Intermediate Similarity	NPC201700
0.7882	Intermediate Similarity	NPC477041
0.7882	Intermediate Similarity	NPC477044
0.7868	Intermediate Similarity	NPC280290
0.784	Intermediate Similarity	NPC472285
0.7834	Intermediate Similarity	NPC476818
0.7833	Intermediate Similarity	NPC227582
0.7831	Intermediate Similarity	NPC311276
0.7831	Intermediate Similarity	NPC40779
0.7816	Intermediate Similarity	NPC476874
0.7816	Intermediate Similarity	NPC155143
0.7816	Intermediate Similarity	NPC260900
0.7804	Intermediate Similarity	NPC473310
0.7778	Intermediate Similarity	NPC163421
0.7778	Intermediate Similarity	NPC188387
0.7767	Intermediate Similarity	NPC475506
0.7756	Intermediate Similarity	NPC477045
0.7746	Intermediate Similarity	NPC474412
0.774	Intermediate Similarity	NPC477043
0.7725	Intermediate Similarity	NPC234999
0.7718	Intermediate Similarity	NPC470497
0.7713	Intermediate Similarity	NPC469762
0.7711	Intermediate Similarity	NPC95783
0.7704	Intermediate Similarity	NPC472443
0.77	Intermediate Similarity	NPC229348
0.7682	Intermediate Similarity	NPC476491
0.768	Intermediate Similarity	NPC314603
0.7678	Intermediate Similarity	NPC162860
0.7677	Intermediate Similarity	NPC472444
0.7677	Intermediate Similarity	NPC469358
0.767	Intermediate Similarity	NPC74413
0.766	Intermediate Similarity	NPC469785
0.7656	Intermediate Similarity	NPC160105
0.7653	Intermediate Similarity	NPC111275
0.765	Intermediate Similarity	NPC235684
0.7644	Intermediate Similarity	NPC476073
0.7626	Intermediate Similarity	NPC71037
0.7624	Intermediate Similarity	NPC206967
0.7621	Intermediate Similarity	NPC473640
0.7614	Intermediate Similarity	NPC270009
0.7612	Intermediate Similarity	NPC278434
0.7606	Intermediate Similarity	NPC70922
0.7606	Intermediate Similarity	NPC211572
0.7606	Intermediate Similarity	NPC80597
0.7606	Intermediate Similarity	NPC212376
0.7606	Intermediate Similarity	NPC75540
0.7602	Intermediate Similarity	NPC267885
0.7598	Intermediate Similarity	NPC474177
0.7594	Intermediate Similarity	NPC107077
0.7594	Intermediate Similarity	NPC223791
0.759	Intermediate Similarity	NPC313791
0.7583	Intermediate Similarity	NPC88008
0.7583	Intermediate Similarity	NPC54420
0.7581	Intermediate Similarity	NPC313640
0.7581	Intermediate Similarity	NPC471284
0.7579	Intermediate Similarity	NPC230869
0.757	Intermediate Similarity	NPC475778
0.7565	Intermediate Similarity	NPC49954
0.7565	Intermediate Similarity	NPC474561
0.7561	Intermediate Similarity	NPC133366
0.7561	Intermediate Similarity	NPC202812
0.7557	Intermediate Similarity	NPC472762
0.7553	Intermediate Similarity	NPC469765
0.7553	Intermediate Similarity	NPC469763
0.7553	Intermediate Similarity	NPC259644
0.7553	Intermediate Similarity	NPC73952
0.7553	Intermediate Similarity	NPC469760
0.7553	Intermediate Similarity	NPC469786
0.7553	Intermediate Similarity	NPC25008
0.7552	Intermediate Similarity	NPC102423
0.7551	Intermediate Similarity	NPC472586
0.7551	Intermediate Similarity	NPC149155
0.7551	Intermediate Similarity	NPC203468
0.7551	Intermediate Similarity	NPC110500
0.7547	Intermediate Similarity	NPC314957
0.7543	Intermediate Similarity	NPC476516
0.7538	Intermediate Similarity	NPC470498
0.7538	Intermediate Similarity	NPC6982
0.7537	Intermediate Similarity	NPC83111
0.7536	Intermediate Similarity	NPC470499
0.7536	Intermediate Similarity	NPC67288
0.7526	Intermediate Similarity	NPC78020
0.7525	Intermediate Similarity	NPC55772
0.7525	Intermediate Similarity	NPC248041
0.7525	Intermediate Similarity	NPC176199
0.7525	Intermediate Similarity	NPC283219
0.7525	Intermediate Similarity	NPC126709
0.7525	Intermediate Similarity	NPC215795
0.7512	Intermediate Similarity	NPC478158
0.75	Intermediate Similarity	NPC100321
0.75	Intermediate Similarity	NPC34508
0.7488	Intermediate Similarity	NPC219087
0.7488	Intermediate Similarity	NPC321708
0.7488	Intermediate Similarity	NPC209917
0.7488	Intermediate Similarity	NPC235900
0.7488	Intermediate Similarity	NPC213629
0.7476	Intermediate Similarity	NPC123019
0.7476	Intermediate Similarity	NPC193761
0.7475	Intermediate Similarity	NPC94752
0.7475	Intermediate Similarity	NPC99428
0.7474	Intermediate Similarity	NPC54988
0.7464	Intermediate Similarity	NPC195461
0.7464	Intermediate Similarity	NPC79129
0.7464	Intermediate Similarity	NPC81654
0.7464	Intermediate Similarity	NPC249150
0.7464	Intermediate Similarity	NPC313985
0.7464	Intermediate Similarity	NPC49196
0.7463	Intermediate Similarity	NPC228835
0.7452	Intermediate Similarity	NPC265576
0.7452	Intermediate Similarity	NPC50503
0.7448	Intermediate Similarity	NPC131718
0.7447	Intermediate Similarity	NPC105818
0.7447	Intermediate Similarity	NPC24678
0.7444	Intermediate Similarity	NPC475258
0.7442	Intermediate Similarity	NPC320968
0.7438	Intermediate Similarity	NPC317030
0.7431	Intermediate Similarity	NPC96131
0.7419	Intermediate Similarity	NPC478157
0.7416	Intermediate Similarity	NPC293917
0.7415	Intermediate Similarity	NPC138370
0.7413	Intermediate Similarity	NPC19679
0.7409	Intermediate Similarity	NPC282231
0.7407	Intermediate Similarity	NPC75634
0.7407	Intermediate Similarity	NPC207020
0.7404	Intermediate Similarity	NPC156704
0.7402	Intermediate Similarity	NPC175474
0.7402	Intermediate Similarity	NPC173028
0.7402	Intermediate Similarity	NPC65215
0.74	Intermediate Similarity	NPC477042
0.74	Intermediate Similarity	NPC198339
0.7399	Intermediate Similarity	NPC319232
0.7399	Intermediate Similarity	NPC24370
0.7397	Intermediate Similarity	NPC477714
0.7397	Intermediate Similarity	NPC281049
0.7397	Intermediate Similarity	NPC264285
0.7393	Intermediate Similarity	NPC328596
0.7393	Intermediate Similarity	NPC328318
0.7389	Intermediate Similarity	NPC62749
0.7389	Intermediate Similarity	NPC89987
0.7387	Intermediate Similarity	NPC145885
0.7387	Intermediate Similarity	NPC68354
0.7387	Intermediate Similarity	NPC14113
0.7387	Intermediate Similarity	NPC84827
0.7385	Intermediate Similarity	NPC476114
0.7381	Intermediate Similarity	NPC214428
0.7374	Intermediate Similarity	NPC37423
0.7374	Intermediate Similarity	NPC275305
0.7371	Intermediate Similarity	NPC194640
0.7368	Intermediate Similarity	NPC171317
0.7368	Intermediate Similarity	NPC149708
0.7368	Intermediate Similarity	NPC473747
0.7366	Intermediate Similarity	NPC476492
0.7363	Intermediate Similarity	NPC233936
0.7358	Intermediate Similarity	NPC279918
0.7353	Intermediate Similarity	NPC204565
0.7353	Intermediate Similarity	NPC17059
0.7349	Intermediate Similarity	NPC469743
0.7347	Intermediate Similarity	NPC63751
0.7347	Intermediate Similarity	NPC154293
0.7342	Intermediate Similarity	NPC16352
0.7336	Intermediate Similarity	NPC323927
0.7336	Intermediate Similarity	NPC166492
0.7336	Intermediate Similarity	NPC473362
0.733	Intermediate Similarity	NPC473763
0.733	Intermediate Similarity	NPC276657
0.733	Intermediate Similarity	NPC117244
0.7321	Intermediate Similarity	NPC909

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 NPC151976 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	519
0.2-0.3	654
0.3-0.4	1869
0.4-0.5	2905
0.5-0.6	2145
0.6-0.7	770
0.7-0.8	113
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
0.7799	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2091	Phase 2
0.7727	Intermediate Similarity	NPD2096	Phase 2
0.7703	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD7957	Phase 1
0.7677	Intermediate Similarity	NPD2095	Phase 2
0.7677	Intermediate Similarity	NPD2094	Phase 2
0.7677	Intermediate Similarity	NPD2092	Phase 2
0.7656	Intermediate Similarity	NPD5426	Phase 3
0.763	Intermediate Similarity	NPD2509	Approved
0.763	Intermediate Similarity	NPD2510	Approved
0.7577	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5901	Discontinued
0.7559	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD482	Approved
0.7536	Intermediate Similarity	NPD7001	Phase 3
0.7535	Intermediate Similarity	NPD8094	Discontinued
0.7523	Intermediate Similarity	NPD7470	Discontinued
0.7513	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6999	Discontinued
0.7488	Intermediate Similarity	NPD8093	Discontinued
0.7477	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD2144	Approved
0.7465	Intermediate Similarity	NPD8399	Phase 1
0.7465	Intermediate Similarity	NPD8423	Phase 2
0.7464	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD4601	Approved
0.7464	Intermediate Similarity	NPD4600	Approved
0.7463	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3038	Discontinued
0.7441	Intermediate Similarity	NPD8072	Approved
0.7438	Intermediate Similarity	NPD8431	Approved
0.7437	Intermediate Similarity	NPD4076	Approved
0.7437	Intermediate Similarity	NPD4079	Approved
0.7416	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6595	Phase 3
0.7387	Intermediate Similarity	NPD3506	Approved
0.7387	Intermediate Similarity	NPD3505	Approved
0.7385	Intermediate Similarity	NPD3389	Approved
0.7385	Intermediate Similarity	NPD3393	Approved
0.7385	Intermediate Similarity	NPD3394	Approved
0.7374	Intermediate Similarity	NPD5065	Approved
0.7371	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2844	Phase 3
0.7336	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD8283	Approved
0.7324	Intermediate Similarity	NPD8282	Approved
0.7324	Intermediate Similarity	NPD8272	Phase 2
0.7324	Intermediate Similarity	NPD56	Approved
0.7323	Intermediate Similarity	NPD750	Phase 2
0.7318	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD8073	Approved
0.7308	Intermediate Similarity	NPD7944	Discontinued
0.7302	Intermediate Similarity	NPD7666	Phase 3
0.7302	Intermediate Similarity	NPD7665	Phase 2
0.7299	Intermediate Similarity	NPD484	Approved
0.7281	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8326	Phase 3
0.7273	Intermediate Similarity	NPD8325	Phase 3
0.7243	Intermediate Similarity	NPD6987	Phase 1
0.7238	Intermediate Similarity	NPD7948	Phase 1
0.7195	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6664	Approved
0.7156	Intermediate Similarity	NPD5003	Discontinued
0.715	Intermediate Similarity	NPD7234	Approved
0.715	Intermediate Similarity	NPD7233	Approved
0.7143	Intermediate Similarity	NPD5897	Approved
0.7143	Intermediate Similarity	NPD7618	Phase 3
0.7143	Intermediate Similarity	NPD7619	Phase 3
0.7143	Intermediate Similarity	NPD5899	Approved
0.7143	Intermediate Similarity	NPD5898	Approved
0.7143	Intermediate Similarity	NPD4427	Phase 2
0.7137	Intermediate Similarity	NPD6165	Phase 2
0.7137	Intermediate Similarity	NPD6164	Phase 2
0.7136	Intermediate Similarity	NPD1325	Approved
0.7136	Intermediate Similarity	NPD1326	Approved
0.7129	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7778	Approved
0.7123	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7777	Approved
0.7123	Intermediate Similarity	NPD53	Approved
0.7118	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3178	Discontinued
0.7103	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6242	Discontinued
0.7091	Intermediate Similarity	NPD4852	Phase 2
0.7091	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7878	Phase 2
0.7083	Intermediate Similarity	NPD8098	Approved
0.7081	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD7824	Approved
0.7073	Intermediate Similarity	NPD5596	Phase 2
0.7059	Intermediate Similarity	NPD3794	Approved
0.7059	Intermediate Similarity	NPD3795	Approved
0.7053	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3871	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3870	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4499	Approved
0.7033	Intermediate Similarity	NPD2564	Approved
0.7033	Intermediate Similarity	NPD2565	Phase 2
0.703	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8289	Discontinued
0.7018	Intermediate Similarity	NPD1392	Approved
0.7014	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD802	Phase 2
0.7005	Intermediate Similarity	NPD3947	Discontinued
0.7005	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2336	Approved
0.7	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4640	Approved
0.7	Intermediate Similarity	NPD4639	Approved
0.7	Intermediate Similarity	NPD4638	Approved
0.6995	Remote Similarity	NPD4463	Approved
0.6995	Remote Similarity	NPD2172	Phase 1
0.6995	Remote Similarity	NPD4462	Approved
0.6995	Remote Similarity	NPD4075	Phase 2
0.6995	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7731	Approved
0.6987	Remote Similarity	NPD7730	Approved
0.6985	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1592	Phase 3
0.6983	Remote Similarity	NPD7790	Approved
0.6983	Remote Similarity	NPD7952	Approved
0.6983	Remote Similarity	NPD7950	Approved
0.6983	Remote Similarity	NPD7953	Approved
0.6983	Remote Similarity	NPD7789	Approved
0.6983	Remote Similarity	NPD7951	Approved
0.6983	Remote Similarity	NPD7791	Approved
0.6977	Remote Similarity	NPD4500	Approved
0.6977	Remote Similarity	NPD4501	Approved
0.6976	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD786	Approved
0.6964	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6176	Phase 1
0.6951	Remote Similarity	NPD7707	Approved
0.6951	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7970	Approved
0.6943	Remote Similarity	NPD7603	Discontinued
0.6937	Remote Similarity	NPD8096	Phase 3
0.6937	Remote Similarity	NPD8097	Phase 3
0.6935	Remote Similarity	NPD5140	Approved
0.6935	Remote Similarity	NPD5138	Approved
0.6935	Remote Similarity	NPD5088	Discontinued
0.6934	Remote Similarity	NPD1038	Approved
0.693	Remote Similarity	NPD6248	Phase 2
0.693	Remote Similarity	NPD6249	Phase 2
0.6927	Remote Similarity	NPD8115	Approved
0.6927	Remote Similarity	NPD8386	Phase 2
0.6927	Remote Similarity	NPD8114	Approved
0.6923	Remote Similarity	NPD4051	Discontinued
0.692	Remote Similarity	NPD5612	Discontinued
0.6919	Remote Similarity	NPD2511	Approved
0.6912	Remote Similarity	NPD5100	Phase 3
0.6901	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7271	Approved
0.6895	Remote Similarity	NPD1722	Approved
0.6893	Remote Similarity	NPD5473	Discontinued
0.6892	Remote Similarity	NPD5066	Phase 2
0.6892	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5067	Phase 2
0.6891	Remote Similarity	NPD4702	Approved
0.6891	Remote Similarity	NPD4703	Approved
0.6887	Remote Similarity	NPD6665	Discontinued
0.6886	Remote Similarity	NPD6995	Phase 1
0.6884	Remote Similarity	NPD7946	Pre-registration
0.6883	Remote Similarity	NPD7781	Approved
0.6883	Remote Similarity	NPD7780	Approved
0.6881	Remote Similarity	NPD2920	Discontinued
0.6878	Remote Similarity	NPD8123	Approved
0.6878	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4181	Approved
0.6878	Remote Similarity	NPD8122	Approved
0.6869	Remote Similarity	NPD2307	Discontinued
0.6866	Remote Similarity	NPD7817	Phase 1
0.6857	Remote Similarity	NPD4948	Discontinued
0.6857	Remote Similarity	NPD3961	Discontinued
0.6856	Remote Similarity	NPD3100	Discontinued
0.685	Remote Similarity	NPD3323	Discontinued
0.6849	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8321	Discontinued
0.6838	Remote Similarity	NPD7558	Phase 2
0.6838	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7187	Phase 2
0.6833	Remote Similarity	NPD8468	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