NPASS Compound

Structure

CID98715 OpenBabel06191715442D 37 41 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 -0.9795 -1.6793 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 -1.7541 -2.3117 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 -2.7339 -2.5117 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 -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 -2.7741 -3.5109 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 -1.6637 -0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 10 2 0 0 0 0 8 13 1 0 0 0 0 8 14 2 0 0 0 0 9 19 1 0 0 0 0 10 24 1 0 0 0 0 11 25 2 0 0 0 0 12 26 2 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 17 23 1 0 0 0 0 18 23 2 0 0 0 0 18 33 1 0 0 0 0 19 1 1 1 0 0 0 20 22 1 0 0 0 0 21 28 1 0 0 0 0 22 4 1 1 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 24 32 1 1 0 0 0 25 26 1 0 0 0 0 26 33 1 0 0 0 0 27 17 1 6 0 0 0 27 30 1 0 0 0 0 27 34 1 0 0 0 0 28 35 1 6 0 0 0 29 36 2 0 0 0 0 30 32 1 1 0 0 0 31 32 1 0 0 0 0 31 34 2 0 0 0 0 31 37 1 0 0 0 0 32 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.29
Volume:	541.245
LogP:	5.409
LogD:	4.322
LogS:	-4.406
# Rotatable Bonds:	2
TPSA:	82.19
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.381
Synthetic Accessibility Score:	5.929
Fsp3:	0.438
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.936
MDCK Permeability:	8.164876817318145e-06
Pgp-inhibitor:	0.064
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.054
20% Bioavailability (F20%):	0.209
30% Bioavailability (F30%):	0.159

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.893
Plasma Protein Binding (PPB):	97.773193359375%
Volume Distribution (VD):	1.581
Pgp-substrate:	3.7533373832702637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.216
CYP1A2-substrate:	0.329
CYP2C19-inhibitor:	0.93
CYP2C19-substrate:	0.587
CYP2C9-inhibitor:	0.796
CYP2C9-substrate:	0.552
CYP2D6-inhibitor:	0.494
CYP2D6-substrate:	0.783
CYP3A4-inhibitor:	0.963
CYP3A4-substrate:	0.275

ADMET: Excretion

Clearance (CL):	8.541
Half-life (T1/2):	0.081

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.284
Drug-inuced Liver Injury (DILI):	0.186
AMES Toxicity:	0.22
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.433
Carcinogencity:	0.368
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC98715

Natural Product ID:	NPC98715
*Common Name:**	Cheatoglobosin T
IUPAC Name:	n.a.
Synonyms:	Cheatoglobosin T
Standard InCHIKey:	KJNZESBAHPOZTI-DYGSJVQXSA-N
Standard InCHI:	InChI=1S/C32H38N2O3/c1-19-9-7-10-24-16-20(2)22(4)30-27(17-23-18-33-26-12-6-5-11-25(23)26)34-31(37)32(24,30)29(36)14-8-13-28(35)21(3)15-19/h5-8,10-12,14-16,18-19,22,24,27-28,30,33,35H,9,13,17H2,1-4H3,(H,34,37)/b10-7+,14-8+,21-15+/t19-,22+,24-,27-,28-,30-,32+/m0/s1
SMILES:	C[C@H]1C/C=C/[C@H]2C=C(C)[C@H]([C@@H]3[C@@]2(C(=O)/C=C/C[C@@H](/C(=C/1)/C)O)C(=N[C@H]3Cc1c[nH]c2c1cccc2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520219
PubChem CID:	11466145
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
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	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
NPT168	Cell Line	P388	Mus musculus	IC50	=	1.58	ug.mL-1	PMID[522751]

☑ 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 NPC98715 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	278
0.1-0.2	1456
0.2-0.3	7776
0.3-0.4	22149
0.4-0.5	6249
0.5-0.6	2238
0.6-0.7	1863
0.7-0.8	642
0.8-0.85	21
0.85-0.9	3
0.9-0.95	11
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9836	High Similarity	NPC225821
0.9836	High Similarity	NPC46225
0.9783	High Similarity	NPC127677
0.9783	High Similarity	NPC258062
0.9574	High Similarity	NPC151976
0.9574	High Similarity	NPC87856
0.9556	High Similarity	NPC195239
0.9556	High Similarity	NPC157828
0.9524	High Similarity	NPC267965
0.9519	High Similarity	NPC271862
0.9503	High Similarity	NPC11445
0.9424	High Similarity	NPC132211
0.9351	High Similarity	NPC300183
0.9323	High Similarity	NPC204491
0.9323	High Similarity	NPC203614
0.9184	High Similarity	NPC2395
0.895	High Similarity	NPC235885
0.895	High Similarity	NPC141428
0.8861	High Similarity	NPC57690
0.8806	High Similarity	NPC147446
0.8627	High Similarity	NPC267926
0.8621	High Similarity	NPC266192
0.8421	Intermediate Similarity	NPC47190
0.837	Intermediate Similarity	NPC151939
0.8324	Intermediate Similarity	NPC213468
0.8286	Intermediate Similarity	NPC290529
0.8281	Intermediate Similarity	NPC267343
0.8242	Intermediate Similarity	NPC201700
0.8214	Intermediate Similarity	NPC252338
0.8182	Intermediate Similarity	NPC300688
0.8177	Intermediate Similarity	NPC311276
0.8125	Intermediate Similarity	NPC154339
0.8112	Intermediate Similarity	NPC477044
0.8112	Intermediate Similarity	NPC131887
0.8112	Intermediate Similarity	NPC477041
0.8105	Intermediate Similarity	NPC280290
0.8061	Intermediate Similarity	NPC227582
0.8056	Intermediate Similarity	NPC469762
0.8037	Intermediate Similarity	NPC70155
0.8	Intermediate Similarity	NPC469785
0.798	Intermediate Similarity	NPC477045
0.7978	Intermediate Similarity	NPC40779
0.796	Intermediate Similarity	NPC477043
0.795	Intermediate Similarity	NPC476874
0.7944	Intermediate Similarity	NPC75540
0.7944	Intermediate Similarity	NPC70922
0.7944	Intermediate Similarity	NPC80597
0.7944	Intermediate Similarity	NPC212376
0.7944	Intermediate Similarity	NPC211572
0.7933	Intermediate Similarity	NPC473310
0.7927	Intermediate Similarity	NPC278434
0.7914	Intermediate Similarity	NPC313791
0.79	Intermediate Similarity	NPC475506
0.7889	Intermediate Similarity	NPC73952
0.7889	Intermediate Similarity	NPC469786
0.7889	Intermediate Similarity	NPC469765
0.7889	Intermediate Similarity	NPC25008
0.7889	Intermediate Similarity	NPC259644
0.7889	Intermediate Similarity	NPC469760
0.7889	Intermediate Similarity	NPC469763
0.788	Intermediate Similarity	NPC102423
0.7877	Intermediate Similarity	NPC476818
0.7876	Intermediate Similarity	NPC315555
0.7861	Intermediate Similarity	NPC6982
0.7861	Intermediate Similarity	NPC155143
0.7861	Intermediate Similarity	NPC260900
0.7846	Intermediate Similarity	NPC206967
0.7846	Intermediate Similarity	NPC95783
0.7842	Intermediate Similarity	NPC215795
0.7842	Intermediate Similarity	NPC176199
0.7831	Intermediate Similarity	NPC267885
0.7819	Intermediate Similarity	NPC34508
0.7817	Intermediate Similarity	NPC474177
0.7805	Intermediate Similarity	NPC162860
0.7804	Intermediate Similarity	NPC476491
0.78	Intermediate Similarity	NPC74413
0.7796	Intermediate Similarity	NPC160105
0.7796	Intermediate Similarity	NPC49954
0.7796	Intermediate Similarity	NPC474561
0.7789	Intermediate Similarity	NPC111275
0.7784	Intermediate Similarity	NPC235684
0.7784	Intermediate Similarity	NPC94752
0.7778	Intermediate Similarity	NPC133366
0.7778	Intermediate Similarity	NPC110500
0.7778	Intermediate Similarity	NPC149155
0.7778	Intermediate Similarity	NPC203468
0.7778	Intermediate Similarity	NPC24678
0.7778	Intermediate Similarity	NPC105818
0.7772	Intermediate Similarity	NPC228835
0.7772	Intermediate Similarity	NPC131718
0.776	Intermediate Similarity	NPC71037
0.7754	Intermediate Similarity	NPC78020
0.775	Intermediate Similarity	NPC473640
0.775	Intermediate Similarity	NPC265576
0.7749	Intermediate Similarity	NPC126709
0.7749	Intermediate Similarity	NPC55772
0.7749	Intermediate Similarity	NPC248041
0.7732	Intermediate Similarity	NPC188387
0.7732	Intermediate Similarity	NPC163421
0.7725	Intermediate Similarity	NPC314603
0.7718	Intermediate Similarity	NPC223791
0.7718	Intermediate Similarity	NPC107077
0.7717	Intermediate Similarity	NPC230869
0.7716	Intermediate Similarity	NPC138370
0.7714	Intermediate Similarity	NPC472285
0.7708	Intermediate Similarity	NPC477042
0.7707	Intermediate Similarity	NPC54420
0.7704	Intermediate Similarity	NPC321708
0.7701	Intermediate Similarity	NPC54988
0.7696	Intermediate Similarity	NPC68354
0.7692	Intermediate Similarity	NPC99428
0.7688	Intermediate Similarity	NPC202812
0.7685	Intermediate Similarity	NPC476073
0.7684	Intermediate Similarity	NPC37423
0.7684	Intermediate Similarity	NPC275305
0.7665	Intermediate Similarity	NPC83111
0.7662	Intermediate Similarity	NPC67288
0.766	Intermediate Similarity	NPC154293
0.7656	Intermediate Similarity	NPC229348
0.7656	Intermediate Similarity	NPC270009
0.7656	Intermediate Similarity	NPC283219
0.7653	Intermediate Similarity	NPC317030
0.7634	Intermediate Similarity	NPC282231
0.7633	Intermediate Similarity	NPC478158
0.7629	Intermediate Similarity	NPC469358
0.7624	Intermediate Similarity	NPC100321
0.7619	Intermediate Similarity	NPC474412
0.7617	Intermediate Similarity	NPC198339
0.7614	Intermediate Similarity	NPC65215
0.7614	Intermediate Similarity	NPC173028
0.7614	Intermediate Similarity	NPC213629
0.7608	Intermediate Similarity	NPC219087
0.7604	Intermediate Similarity	NPC293472
0.7604	Intermediate Similarity	NPC84827
0.7604	Intermediate Similarity	NPC284775
0.7604	Intermediate Similarity	NPC145885
0.7604	Intermediate Similarity	NPC14113
0.7598	Intermediate Similarity	NPC123019
0.7598	Intermediate Similarity	NPC193761
0.7594	Intermediate Similarity	NPC194640
0.7592	Intermediate Similarity	NPC293216
0.7586	Intermediate Similarity	NPC470497
0.7581	Intermediate Similarity	NPC279918
0.7579	Intermediate Similarity	NPC470498
0.7577	Intermediate Similarity	NPC192270
0.7577	Intermediate Similarity	NPC233936
0.7574	Intermediate Similarity	NPC473747
0.7573	Intermediate Similarity	NPC475288
0.7566	Intermediate Similarity	NPC63751
0.7565	Intermediate Similarity	NPC472443
0.7565	Intermediate Similarity	NPC11126
0.7563	Intermediate Similarity	NPC17059
0.7563	Intermediate Similarity	NPC204565
0.756	Intermediate Similarity	NPC320968
0.7556	Intermediate Similarity	NPC159856
0.7556	Intermediate Similarity	NPC314372
0.7554	Intermediate Similarity	NPC470507
0.7553	Intermediate Similarity	NPC42372
0.7538	Intermediate Similarity	NPC19679
0.7538	Intermediate Similarity	NPC472444
0.7536	Intermediate Similarity	NPC478157
0.7527	Intermediate Similarity	NPC135141
0.7527	Intermediate Similarity	NPC92796
0.7526	Intermediate Similarity	NPC194411
0.7525	Intermediate Similarity	NPC175474
0.7525	Intermediate Similarity	NPC209917
0.7525	Intermediate Similarity	NPC229332
0.7513	Intermediate Similarity	NPC474707
0.7513	Intermediate Similarity	NPC62749
0.7512	Intermediate Similarity	NPC181502
0.7512	Intermediate Similarity	NPC328318
0.7512	Intermediate Similarity	NPC85066
0.7512	Intermediate Similarity	NPC264285
0.7512	Intermediate Similarity	NPC234999
0.7512	Intermediate Similarity	NPC472762
0.7512	Intermediate Similarity	NPC281049
0.7512	Intermediate Similarity	NPC328596
0.75	Intermediate Similarity	NPC49196
0.75	Intermediate Similarity	NPC249150
0.75	Intermediate Similarity	NPC195461
0.75	Intermediate Similarity	NPC79129
0.75	Intermediate Similarity	NPC477003
0.75	Intermediate Similarity	NPC45459
0.75	Intermediate Similarity	NPC171787
0.75	Intermediate Similarity	NPC315491
0.75	Intermediate Similarity	NPC313985
0.75	Intermediate Similarity	NPC81654
0.7488	Intermediate Similarity	NPC50503
0.7488	Intermediate Similarity	NPC171317
0.7477	Intermediate Similarity	NPC475258
0.7473	Intermediate Similarity	NPC286427
0.7464	Intermediate Similarity	NPC284102
0.7453	Intermediate Similarity	NPC471284
0.7453	Intermediate Similarity	NPC313640
0.7452	Intermediate Similarity	NPC88008
0.7452	Intermediate Similarity	NPC473362
0.7452	Intermediate Similarity	NPC166492
0.7451	Intermediate Similarity	NPC293917
0.745	Intermediate Similarity	NPC476460
0.745	Intermediate Similarity	NPC117244

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 NPC98715 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	511
0.2-0.3	666
0.3-0.4	1749
0.4-0.5	2806
0.5-0.6	2256
0.6-0.7	839
0.7-0.8	141
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
0.8	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD2509	Approved
0.7931	Intermediate Similarity	NPD2510	Approved
0.7865	Intermediate Similarity	NPD2091	Phase 2
0.7865	Intermediate Similarity	NPD2096	Phase 2
0.7843	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD8094	Discontinued
0.7812	Intermediate Similarity	NPD2094	Phase 2
0.7812	Intermediate Similarity	NPD2092	Phase 2
0.7812	Intermediate Similarity	NPD2095	Phase 2
0.7789	Intermediate Similarity	NPD2144	Approved
0.7778	Intermediate Similarity	NPD8093	Discontinued
0.7778	Intermediate Similarity	NPD482	Approved
0.7772	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD3038	Discontinued
0.7749	Intermediate Similarity	NPD4076	Approved
0.7749	Intermediate Similarity	NPD4079	Approved
0.7737	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD3505	Approved
0.7696	Intermediate Similarity	NPD5426	Phase 3
0.7696	Intermediate Similarity	NPD5901	Discontinued
0.7696	Intermediate Similarity	NPD3506	Approved
0.7684	Intermediate Similarity	NPD5065	Approved
0.7667	Intermediate Similarity	NPD3389	Approved
0.7667	Intermediate Similarity	NPD3394	Approved
0.7667	Intermediate Similarity	NPD3393	Approved
0.766	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7659	Intermediate Similarity	NPD7001	Phase 3
0.7659	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7470	Discontinued
0.7626	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD6999	Discontinued
0.7621	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD6595	Phase 3
0.7596	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD7957	Phase 1
0.7573	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD8431	Approved
0.7539	Intermediate Similarity	NPD750	Phase 2
0.7536	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD484	Approved
0.75	Intermediate Similarity	NPD4601	Approved
0.75	Intermediate Similarity	NPD4600	Approved
0.7474	Intermediate Similarity	NPD2844	Phase 3
0.7451	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6664	Approved
0.743	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7618	Phase 3
0.7426	Intermediate Similarity	NPD7619	Phase 3
0.7426	Intermediate Similarity	NPD7944	Discontinued
0.7416	Intermediate Similarity	NPD7666	Phase 3
0.7416	Intermediate Similarity	NPD7665	Phase 2
0.7393	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8072	Approved
0.7387	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6987	Phase 1
0.7356	Intermediate Similarity	NPD8272	Phase 2
0.7353	Intermediate Similarity	NPD7948	Phase 1
0.735	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5899	Approved
0.7347	Intermediate Similarity	NPD5897	Approved
0.7347	Intermediate Similarity	NPD5898	Approved
0.7337	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3871	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3870	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3178	Discontinued
0.7297	Intermediate Similarity	NPD4462	Approved
0.7297	Intermediate Similarity	NPD2172	Phase 1
0.7297	Intermediate Similarity	NPD4463	Approved
0.7295	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1592	Phase 3
0.7292	Intermediate Similarity	NPD4638	Approved
0.7292	Intermediate Similarity	NPD4639	Approved
0.7292	Intermediate Similarity	NPD4640	Approved
0.7286	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4075	Phase 2
0.7281	Intermediate Similarity	NPD6242	Discontinued
0.7278	Intermediate Similarity	NPD786	Approved
0.7277	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5596	Phase 2
0.7268	Intermediate Similarity	NPD5003	Discontinued
0.7264	Intermediate Similarity	NPD7234	Approved
0.7264	Intermediate Similarity	NPD7233	Approved
0.726	Intermediate Similarity	NPD8073	Approved
0.7254	Intermediate Similarity	NPD1326	Approved
0.7254	Intermediate Similarity	NPD1325	Approved
0.724	Intermediate Similarity	NPD6165	Phase 2
0.724	Intermediate Similarity	NPD6164	Phase 2
0.7233	Intermediate Similarity	NPD7778	Approved
0.7233	Intermediate Similarity	NPD7777	Approved
0.7233	Intermediate Similarity	NPD53	Approved
0.7228	Intermediate Similarity	NPD4499	Approved
0.7225	Intermediate Similarity	NPD6176	Phase 1
0.7225	Intermediate Similarity	NPD5138	Approved
0.7225	Intermediate Similarity	NPD5140	Approved
0.7222	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2511	Approved
0.7206	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD1722	Approved
0.7196	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD56	Approved
0.719	Intermediate Similarity	NPD8283	Approved
0.719	Intermediate Similarity	NPD8282	Approved
0.7189	Intermediate Similarity	NPD4703	Approved
0.7189	Intermediate Similarity	NPD4702	Approved
0.7183	Intermediate Similarity	NPD4051	Discontinued
0.7172	Intermediate Similarity	NPD5473	Discontinued
0.717	Intermediate Similarity	NPD8423	Phase 2
0.717	Intermediate Similarity	NPD8399	Phase 1
0.7157	Intermediate Similarity	NPD4181	Approved
0.7151	Intermediate Similarity	NPD3100	Discontinued
0.715	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8326	Phase 3
0.7143	Intermediate Similarity	NPD2564	Approved
0.7143	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2565	Phase 2
0.7143	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8325	Phase 3
0.7135	Intermediate Similarity	NPD5088	Discontinued
0.7135	Intermediate Similarity	NPD3323	Discontinued
0.7129	Intermediate Similarity	NPD3961	Discontinued
0.7122	Intermediate Similarity	NPD1038	Approved
0.7117	Intermediate Similarity	NPD8289	Discontinued
0.7116	Intermediate Similarity	NPD4852	Phase 2
0.7111	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7878	Phase 2
0.7108	Intermediate Similarity	NPD2336	Approved
0.7107	Intermediate Similarity	NPD2381	Approved
0.7107	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2380	Approved
0.7107	Intermediate Similarity	NPD2382	Approved
0.7098	Intermediate Similarity	NPD7824	Approved
0.7098	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7187	Phase 2
0.7083	Intermediate Similarity	NPD3794	Approved
0.7083	Intermediate Similarity	NPD3795	Approved
0.7081	Intermediate Similarity	NPD4501	Approved
0.7081	Intermediate Similarity	NPD4500	Approved
0.7081	Intermediate Similarity	NPD6479	Discontinued
0.7072	Intermediate Similarity	NPD7269	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8123	Approved
0.7071	Intermediate Similarity	NPD8122	Approved
0.707	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7564	Discontinued
0.7065	Intermediate Similarity	NPD6178	Phase 3
0.7059	Intermediate Similarity	NPD6281	Approved
0.7056	Intermediate Similarity	NPD4128	Approved
0.7053	Intermediate Similarity	NPD6026	Approved
0.7044	Intermediate Similarity	NPD4948	Discontinued
0.704	Intermediate Similarity	NPD7603	Discontinued
0.7035	Intermediate Similarity	NPD8386	Phase 2
0.7028	Intermediate Similarity	NPD8114	Approved
0.7028	Intermediate Similarity	NPD3947	Discontinued
0.7028	Intermediate Similarity	NPD8115	Approved
0.7028	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5100	Phase 3
0.7015	Intermediate Similarity	NPD3320	Approved
0.7015	Intermediate Similarity	NPD3319	Phase 1
0.7015	Intermediate Similarity	NPD3318	Approved
0.7009	Intermediate Similarity	NPD7731	Approved
0.7009	Intermediate Similarity	NPD7730	Approved
0.7005	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD7953	Approved
0.7004	Intermediate Similarity	NPD7951	Approved
0.7004	Intermediate Similarity	NPD7790	Approved
0.7004	Intermediate Similarity	NPD7791	Approved
0.7004	Intermediate Similarity	NPD7952	Approved
0.7004	Intermediate Similarity	NPD7950	Approved
0.7004	Intermediate Similarity	NPD7789	Approved
0.7	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2481	Approved
0.7	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2479	Phase 3
0.6995	Remote Similarity	NPD7010	Phase 3
0.6991	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3404	Approved
0.6986	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6995	Phase 1
0.6981	Remote Similarity	NPD2920	Discontinued
0.6978	Remote Similarity	NPD7780	Approved
0.6978	Remote Similarity	NPD7781	Approved
0.6977	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD3717	Discontinued
0.6972	Remote Similarity	NPD7707	Approved
0.6971	Remote Similarity	NPD2307	Discontinued
0.6968	Remote Similarity	NPD4374	Clinical (unspecified phase)

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