NPASS Compound

Structure

NPC252338 OpenBabel07101718202D 37 41 0 0 0 0 0 0 0 0999 V2000 -3.8994 -1.7929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8904 -1.7061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6339 -2.8375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4589 -1.9236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6135 -1.4355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4113 -0.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7582 -0.5159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2030 2.9072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6036 -0.0278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0484 2.4191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9128 -0.0278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6424 2.4191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6036 0.9484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0484 1.4430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2824 -1.1836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5840 -0.2552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5844 2.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9355 -1.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9128 0.9484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6424 1.4430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9308 0.4702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1873 1.6016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7582 1.4365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2030 0.9549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2325 1.3986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3679 0.7898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3228 0.9927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9760 0.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5793 2.1241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6244 1.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9708 -0.1020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4589 -0.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5552 2.3914 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 -2.6743 -0.6611 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8809 3.0525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9712 2.6466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 32 1 0 0 0 0 5 32 1 0 0 0 0 6 32 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 19 2 0 0 0 0 12 20 2 0 0 0 0 13 23 2 0 0 0 0 14 24 2 0 0 0 0 15 16 1 0 0 0 0 15 18 2 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 17 33 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 20 26 1 0 0 0 0 21 25 2 0 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 23 33 1 0 0 0 0 24 34 1 0 0 0 0 25 29 1 0 0 0 0 26 27 1 0 0 0 0 26 31 2 0 0 0 0 27 28 1 0 0 0 0 27 30 2 0 0 0 0 28 35 2 0 0 0 0 29 30 1 0 0 0 0 29 36 2 0 0 0 0 30 37 1 0 0 0 0 31 32 1 0 0 0 0 31 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.23
Volume:	530.699
LogP:	7.33
LogD:	4.278
LogS:	-3.444
# Rotatable Bonds:	6
TPSA:	92.27
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.072
Synthetic Accessibility Score:	3.401
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.945
MDCK Permeability:	1.1712389095919207e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.223
30% Bioavailability (F30%):	0.042

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	102.26660919189453%
Volume Distribution (VD):	0.327
Pgp-substrate:	0.6036876440048218%

ADMET: Metabolism

CYP1A2-inhibitor:	0.916
CYP1A2-substrate:	0.249
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.791
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.247
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	1.41
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.25
Human Hepatotoxicity (H-HT):	0.24
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.709
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.891
Carcinogencity:	0.13
Eye Corrosion:	0.003
Eye Irritation:	0.304
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC252338

Natural Product ID:	NPC252338
*Common Name:**	Terrequinone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HBMHEGGZNWXZRA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H30N2O3/c1-6-32(4,5)31-26(20-12-8-10-14-24(20)34-31)27-28(35)21(16-15-18(2)3)25(29(36)30(27)37)22-17-33-23-13-9-7-11-19(22)23/h6-15,17,33-34,37H,1,16H2,2-5H3
SMILES:	C=CC(c1[nH]c2c(c1C1=C(O)C(=O)C(=C(C1=O)CC=C(C)C)c1c[nH]c3c1cccc3)cccc2)(C)C
Synthetic Gene Cluster:	BGC0000442;
ChEMBL Identifier:	CHEMBL485268
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	5600.0	nM	PMID[569215]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6800.0	nM	PMID[569215]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	13900.0	nM	PMID[569215]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	5400.0	nM	PMID[569215]

☑ 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 NPC252338 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	346
0.1-0.2	1971
0.2-0.3	11189
0.3-0.4	20362
0.4-0.5	4416
0.5-0.6	1763
0.6-0.7	1850
0.7-0.8	735
0.8-0.85	53
0.85-0.9	8
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9831	High Similarity	NPC227582
0.9454	High Similarity	NPC260900
0.9396	High Similarity	NPC74413
0.8724	High Similarity	NPC474412
0.8723	High Similarity	NPC131887
0.8706	High Similarity	NPC476818
0.8696	High Similarity	NPC321708
0.8667	High Similarity	NPC55772
0.8519	High Similarity	NPC11445
0.8466	Intermediate Similarity	NPC157828
0.8466	Intermediate Similarity	NPC195239
0.8457	Intermediate Similarity	NPC47190
0.8446	Intermediate Similarity	NPC476073
0.8429	Intermediate Similarity	NPC67288
0.8407	Intermediate Similarity	NPC59269
0.8361	Intermediate Similarity	NPC213468
0.8325	Intermediate Similarity	NPC258062
0.8307	Intermediate Similarity	NPC476460
0.8306	Intermediate Similarity	NPC111275
0.8278	Intermediate Similarity	NPC78020
0.8274	Intermediate Similarity	NPC225821
0.8254	Intermediate Similarity	NPC154339
0.8251	Intermediate Similarity	NPC267885
0.8235	Intermediate Similarity	NPC276657
0.8227	Intermediate Similarity	NPC264285
0.822	Intermediate Similarity	NPC267343
0.822	Intermediate Similarity	NPC304203
0.8214	Intermediate Similarity	NPC98715
0.82	Intermediate Similarity	NPC82370
0.8197	Intermediate Similarity	NPC149155
0.8197	Intermediate Similarity	NPC110500
0.8197	Intermediate Similarity	NPC203468
0.8191	Intermediate Similarity	NPC235684
0.8177	Intermediate Similarity	NPC63751
0.8163	Intermediate Similarity	NPC193761
0.8162	Intermediate Similarity	NPC126709
0.8162	Intermediate Similarity	NPC248041
0.8159	Intermediate Similarity	NPC87856
0.8141	Intermediate Similarity	NPC127677
0.8138	Intermediate Similarity	NPC99939
0.8138	Intermediate Similarity	NPC308931
0.8128	Intermediate Similarity	NPC203614
0.8128	Intermediate Similarity	NPC132211
0.8116	Intermediate Similarity	NPC229893
0.8108	Intermediate Similarity	NPC284775
0.81	Intermediate Similarity	NPC271862
0.8095	Intermediate Similarity	NPC315555
0.8095	Intermediate Similarity	NPC62749
0.809	Intermediate Similarity	NPC46225
0.8079	Intermediate Similarity	NPC478157
0.8068	Intermediate Similarity	NPC16352
0.8065	Intermediate Similarity	NPC283219
0.8053	Intermediate Similarity	NPC17059
0.8042	Intermediate Similarity	NPC15102
0.8022	Intermediate Similarity	NPC474561
0.8022	Intermediate Similarity	NPC49954
0.802	Intermediate Similarity	NPC300183
0.8011	Intermediate Similarity	NPC84827
0.8011	Intermediate Similarity	NPC14113
0.8011	Intermediate Similarity	NPC151939
0.8011	Intermediate Similarity	NPC145885
0.801	Intermediate Similarity	NPC478158
0.7981	Intermediate Similarity	NPC70155
0.798	Intermediate Similarity	NPC151976
0.7978	Intermediate Similarity	NPC211572
0.7978	Intermediate Similarity	NPC70922
0.7978	Intermediate Similarity	NPC80597
0.7978	Intermediate Similarity	NPC212376
0.7978	Intermediate Similarity	NPC75540
0.7956	Intermediate Similarity	NPC282231
0.7951	Intermediate Similarity	NPC36405
0.7951	Intermediate Similarity	NPC204491
0.7944	Intermediate Similarity	NPC135141
0.7944	Intermediate Similarity	NPC92796
0.7943	Intermediate Similarity	NPC147446
0.7941	Intermediate Similarity	NPC267965
0.794	Intermediate Similarity	NPC317701
0.7938	Intermediate Similarity	NPC326422
0.7923	Intermediate Similarity	NPC160105
0.7921	Intermediate Similarity	NPC469760
0.7921	Intermediate Similarity	NPC469763
0.7921	Intermediate Similarity	NPC73952
0.7921	Intermediate Similarity	NPC469765
0.7921	Intermediate Similarity	NPC25008
0.7921	Intermediate Similarity	NPC469786
0.7921	Intermediate Similarity	NPC259644
0.7921	Intermediate Similarity	NPC162860
0.7917	Intermediate Similarity	NPC213629
0.7914	Intermediate Similarity	NPC64436
0.7912	Intermediate Similarity	NPC311276
0.791	Intermediate Similarity	NPC54420
0.7901	Intermediate Similarity	NPC279918
0.7889	Intermediate Similarity	NPC476874
0.788	Intermediate Similarity	NPC201700
0.7874	Intermediate Similarity	NPC473310
0.7874	Intermediate Similarity	NPC477714
0.7868	Intermediate Similarity	NPC171317
0.7849	Intermediate Similarity	NPC314603
0.7847	Intermediate Similarity	NPC2395
0.7826	Intermediate Similarity	NPC477715
0.7826	Intermediate Similarity	NPC472285
0.782	Intermediate Similarity	NPC235885
0.782	Intermediate Similarity	NPC141428
0.7814	Intermediate Similarity	NPC194640
0.7812	Intermediate Similarity	NPC94752
0.7811	Intermediate Similarity	NPC477043
0.7809	Intermediate Similarity	NPC53947
0.7805	Intermediate Similarity	NPC75634
0.7805	Intermediate Similarity	NPC110182
0.7801	Intermediate Similarity	NPC477003
0.7801	Intermediate Similarity	NPC228835
0.779	Intermediate Similarity	NPC469762
0.7789	Intermediate Similarity	NPC213308
0.7784	Intermediate Similarity	NPC83111
0.7783	Intermediate Similarity	NPC267926
0.7778	Intermediate Similarity	NPC477041
0.7778	Intermediate Similarity	NPC248462
0.7778	Intermediate Similarity	NPC477044
0.7767	Intermediate Similarity	NPC207686
0.7746	Intermediate Similarity	NPC57690
0.774	Intermediate Similarity	NPC288838
0.7737	Intermediate Similarity	NPC300688
0.7737	Intermediate Similarity	NPC91179
0.7735	Intermediate Similarity	NPC469785
0.773	Intermediate Similarity	NPC54988
0.7725	Intermediate Similarity	NPC248454
0.7723	Intermediate Similarity	NPC473376
0.7721	Intermediate Similarity	NPC290529
0.7718	Intermediate Similarity	NPC153980
0.7718	Intermediate Similarity	NPC6865
0.7716	Intermediate Similarity	NPC202812
0.7706	Intermediate Similarity	NPC15801
0.7703	Intermediate Similarity	NPC178858
0.7696	Intermediate Similarity	NPC71037
0.7689	Intermediate Similarity	NPC266192
0.7685	Intermediate Similarity	NPC175602
0.7685	Intermediate Similarity	NPC472064
0.7684	Intermediate Similarity	NPC314372
0.7684	Intermediate Similarity	NPC11126
0.7684	Intermediate Similarity	NPC219336
0.768	Intermediate Similarity	NPC278434
0.767	Intermediate Similarity	NPC72956
0.7668	Intermediate Similarity	NPC280290
0.7664	Intermediate Similarity	NPC476491
0.7662	Intermediate Similarity	NPC475506
0.7659	Intermediate Similarity	NPC61038
0.7656	Intermediate Similarity	NPC469358
0.765	Intermediate Similarity	NPC477045
0.765	Intermediate Similarity	NPC230869
0.765	Intermediate Similarity	NPC293917
0.7644	Intermediate Similarity	NPC477042
0.7638	Intermediate Similarity	NPC262898
0.7638	Intermediate Similarity	NPC167710
0.7637	Intermediate Similarity	NPC285469
0.7633	Intermediate Similarity	NPC75726
0.7633	Intermediate Similarity	NPC219087
0.7633	Intermediate Similarity	NPC31385
0.7633	Intermediate Similarity	NPC207020
0.7633	Intermediate Similarity	NPC110602
0.7632	Intermediate Similarity	NPC183662
0.7632	Intermediate Similarity	NPC15573
0.7632	Intermediate Similarity	NPC217372
0.7624	Intermediate Similarity	NPC155143
0.7622	Intermediate Similarity	NPC40779
0.7619	Intermediate Similarity	NPC139763
0.7614	Intermediate Similarity	NPC67551
0.7614	Intermediate Similarity	NPC99666
0.7612	Intermediate Similarity	NPC45459
0.7612	Intermediate Similarity	NPC315491
0.7604	Intermediate Similarity	NPC63031
0.7604	Intermediate Similarity	NPC191415
0.7602	Intermediate Similarity	NPC329858
0.7602	Intermediate Similarity	NPC95783
0.7602	Intermediate Similarity	NPC472112
0.76	Intermediate Similarity	NPC149708
0.76	Intermediate Similarity	NPC473640
0.7596	Intermediate Similarity	NPC216643
0.7593	Intermediate Similarity	NPC326363
0.7588	Intermediate Similarity	NPC179701
0.7576	Intermediate Similarity	NPC88315
0.7571	Intermediate Similarity	NPC190296
0.7571	Intermediate Similarity	NPC27041
0.7565	Intermediate Similarity	NPC163055
0.7562	Intermediate Similarity	NPC153123
0.7562	Intermediate Similarity	NPC201266
0.7562	Intermediate Similarity	NPC220797
0.7562	Intermediate Similarity	NPC474318
0.7562	Intermediate Similarity	NPC268744
0.7562	Intermediate Similarity	NPC475914
0.7562	Intermediate Similarity	NPC100321
0.7561	Intermediate Similarity	NPC323927
0.755	Intermediate Similarity	NPC272483
0.7548	Intermediate Similarity	NPC471194
0.7548	Intermediate Similarity	NPC471193
0.7537	Intermediate Similarity	NPC472069
0.7537	Intermediate Similarity	NPC328318
0.7537	Intermediate Similarity	NPC472063
0.7537	Intermediate Similarity	NPC328596
0.7537	Intermediate Similarity	NPC472062
0.7536	Intermediate Similarity	NPC281049

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 NPC252338 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	575
0.2-0.3	718
0.3-0.4	1910
0.4-0.5	2685
0.5-0.6	2046
0.6-0.7	843
0.7-0.8	150
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8549	High Similarity	NPD5426	Phase 3
0.8315	Intermediate Similarity	NPD6595	Phase 3
0.8251	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8197	Intermediate Similarity	NPD482	Approved
0.8196	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.8196	Intermediate Similarity	NPD6999	Discontinued
0.8182	Intermediate Similarity	NPD2091	Phase 2
0.8182	Intermediate Similarity	NPD2096	Phase 2
0.8173	Intermediate Similarity	NPD5901	Discontinued
0.8138	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8128	Intermediate Similarity	NPD2094	Phase 2
0.8128	Intermediate Similarity	NPD2092	Phase 2
0.8128	Intermediate Similarity	NPD2095	Phase 2
0.8081	Intermediate Similarity	NPD6987	Phase 1
0.806	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.802	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.796	Intermediate Similarity	NPD7665	Phase 2
0.796	Intermediate Similarity	NPD7666	Phase 3
0.795	Intermediate Similarity	NPD7001	Phase 3
0.7946	Intermediate Similarity	NPD750	Phase 2
0.7937	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD8431	Approved
0.7861	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7470	Discontinued
0.7838	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7948	Phase 1
0.7716	Intermediate Similarity	NPD7618	Phase 3
0.7716	Intermediate Similarity	NPD7619	Phase 3
0.7713	Intermediate Similarity	NPD5065	Approved
0.7703	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD6165	Phase 2
0.7664	Intermediate Similarity	NPD6164	Phase 2
0.765	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4852	Phase 2
0.7633	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6242	Discontinued
0.7629	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD7944	Discontinued
0.7624	Intermediate Similarity	NPD8073	Approved
0.7612	Intermediate Similarity	NPD484	Approved
0.761	Intermediate Similarity	NPD2509	Approved
0.761	Intermediate Similarity	NPD2510	Approved
0.7598	Intermediate Similarity	NPD7957	Phase 1
0.7598	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD8093	Discontinued
0.7524	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2172	Phase 1
0.7513	Intermediate Similarity	NPD4499	Approved
0.7512	Intermediate Similarity	NPD2008	Discontinued
0.7512	Intermediate Similarity	NPD8094	Discontinued
0.75	Intermediate Similarity	NPD8072	Approved
0.75	Intermediate Similarity	NPD2844	Phase 3
0.7464	Intermediate Similarity	NPD2411	Approved
0.7431	Intermediate Similarity	NPD7824	Approved
0.7419	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4848	Phase 1
0.7409	Intermediate Similarity	NPD7952	Approved
0.7409	Intermediate Similarity	NPD4076	Approved
0.7409	Intermediate Similarity	NPD7950	Approved
0.7409	Intermediate Similarity	NPD7789	Approved
0.7409	Intermediate Similarity	NPD7953	Approved
0.7409	Intermediate Similarity	NPD4079	Approved
0.7409	Intermediate Similarity	NPD7791	Approved
0.7409	Intermediate Similarity	NPD7951	Approved
0.7409	Intermediate Similarity	NPD7790	Approved
0.7406	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD5818	Discontinued
0.7387	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7781	Approved
0.7385	Intermediate Similarity	NPD7780	Approved
0.7381	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD6664	Approved
0.7373	Intermediate Similarity	NPD7603	Discontinued
0.7363	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3506	Approved
0.7358	Intermediate Similarity	NPD3505	Approved
0.7358	Intermediate Similarity	NPD2144	Approved
0.7353	Intermediate Similarity	NPD4601	Approved
0.7353	Intermediate Similarity	NPD4600	Approved
0.7351	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6178	Phase 3
0.7346	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7731	Approved
0.7339	Intermediate Similarity	NPD7730	Approved
0.7339	Intermediate Similarity	NPD4845	Discontinued
0.7333	Intermediate Similarity	NPD3178	Discontinued
0.733	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD8386	Phase 2
0.7316	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6995	Phase 1
0.7303	Intermediate Similarity	NPD786	Approved
0.7296	Intermediate Similarity	NPD3320	Approved
0.7296	Intermediate Similarity	NPD3318	Approved
0.7296	Intermediate Similarity	NPD3319	Phase 1
0.7295	Intermediate Similarity	NPD8282	Approved
0.7295	Intermediate Similarity	NPD56	Approved
0.7295	Intermediate Similarity	NPD8283	Approved
0.7282	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5473	Discontinued
0.7277	Intermediate Similarity	NPD3394	Approved
0.7277	Intermediate Similarity	NPD1326	Approved
0.7277	Intermediate Similarity	NPD1325	Approved
0.7277	Intermediate Similarity	NPD3393	Approved
0.7277	Intermediate Similarity	NPD3389	Approved
0.7268	Intermediate Similarity	NPD7865	Approved
0.7265	Intermediate Similarity	NPD6530	Approved
0.7265	Intermediate Similarity	NPD6531	Approved
0.7259	Intermediate Similarity	NPD7564	Discontinued
0.7257	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7271	Approved
0.7246	Intermediate Similarity	NPD6176	Phase 1
0.7245	Intermediate Similarity	NPD3038	Discontinued
0.7243	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4948	Discontinued
0.7233	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5017	Discontinued
0.7232	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7970	Approved
0.723	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4463	Approved
0.7228	Intermediate Similarity	NPD4462	Approved
0.7228	Intermediate Similarity	NPD1038	Approved
0.7222	Intermediate Similarity	NPD1722	Approved
0.722	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4075	Phase 2
0.7214	Intermediate Similarity	NPD2336	Approved
0.7212	Intermediate Similarity	NPD3947	Discontinued
0.7212	Intermediate Similarity	NPD8272	Phase 2
0.7206	Intermediate Similarity	NPD5003	Discontinued
0.72	Intermediate Similarity	NPD1534	Approved
0.7198	Intermediate Similarity	NPD7187	Phase 2
0.7195	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6217	Discontinued
0.7174	Intermediate Similarity	NPD3100	Discontinued
0.7157	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2837	Discontinued
0.7143	Intermediate Similarity	NPD8322	Phase 2
0.7136	Intermediate Similarity	NPD7711	Discontinued
0.7136	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD8098	Approved
0.7128	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4051	Discontinued
0.7122	Intermediate Similarity	NPD2880	Discontinued
0.712	Intermediate Similarity	NPD4703	Approved
0.712	Intermediate Similarity	NPD4702	Approved
0.7115	Intermediate Similarity	NPD2879	Approved
0.7115	Intermediate Similarity	NPD2881	Approved
0.7112	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4602	Approved
0.7108	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2481	Approved
0.7107	Intermediate Similarity	NPD2479	Phase 3
0.7101	Intermediate Similarity	NPD4501	Approved
0.7101	Intermediate Similarity	NPD4500	Approved
0.7098	Intermediate Similarity	NPD1573	Approved
0.7098	Intermediate Similarity	NPD1575	Approved
0.7095	Intermediate Similarity	NPD7568	Phase 1
0.7094	Intermediate Similarity	NPD3404	Approved
0.7089	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4397	Phase 1
0.7083	Intermediate Similarity	NPD2639	Approved
0.7083	Intermediate Similarity	NPD2642	Approved
0.7077	Intermediate Similarity	NPD4128	Approved
0.7073	Intermediate Similarity	NPD2307	Discontinued
0.7068	Intermediate Similarity	NPD5088	Discontinued
0.7068	Intermediate Similarity	NPD3323	Discontinued
0.7065	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3961	Discontinued
0.7065	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3905	Phase 3
0.7059	Intermediate Similarity	NPD802	Phase 2
0.7059	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5471	Phase 3
0.7031	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD2443	Approved
0.7028	Intermediate Similarity	NPD8423	Phase 2
0.7028	Intermediate Similarity	NPD2442	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