NPASS Compound

Structure

CID225051 OpenBabel06191716022D 23 26 0 0 0 0 0 0 0 0999 V2000 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 11 1 0 0 0 0 4 13 2 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 10 15 2 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 22 2 0 0 0 0 19 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.07
Volume:	311.751
LogP:	4.962
LogD:	3.126
LogS:	-6.911
# Rotatable Bonds:	0
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.522
Synthetic Accessibility Score:	2.366
Fsp3:	0.053
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.057
MDCK Permeability:	1.4865065168123692e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	100.24614715576172%
Volume Distribution (VD):	0.427
Pgp-substrate:	0.7218822836875916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.212
CYP2C19-inhibitor:	0.535
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.563
CYP2C9-substrate:	0.622
CYP2D6-inhibitor:	0.432
CYP2D6-substrate:	0.245
CYP3A4-inhibitor:	0.365
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	6.053
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.83
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.819
Carcinogencity:	0.952
Eye Corrosion:	0.005
Eye Irritation:	0.978
Respiratory Toxicity:	0.058

Download Data

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

Natural Product: NPC225051

Natural Product ID:	NPC225051
*Common Name:**	Tetrangulol
IUPAC Name:	1,8-dihydroxy-3-methylbenzo[a]anthracene-7,12-dione
Synonyms:	Tetrangulol
Standard InCHIKey:	NFUYRESOTVGLRL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H12O4/c1-9-7-10-5-6-12-17(15(10)14(21)8-9)19(23)11-3-2-4-13(20)16(11)18(12)22/h2-8,20-21H,1H3
SMILES:	Cc1cc(O)c2c(c1)ccc1c2C(=O)c2cccc(c2C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668340
PubChem CID:	99188
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003415] Angucyclines

*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
NPO19685	Streptomyces cyanogenus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21188999]
NPO19685	Streptomyces cyanogenus	Species	Streptomycetaceae	Bacteria	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
GI50	60
IC50	1

Activity Type	# Activity
Cell Line	60
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	188.36	nM	PMID[511322]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	72610.6	nM	PMID[511322]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	17701.09	nM	PMID[511322]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	3981.07	nM	PMID[511322]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[511322]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[511322]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	4560.37	nM	PMID[511322]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	691.83	nM	PMID[511322]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	329.61	nM	PMID[511322]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	7638.36	nM	PMID[511322]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	18578.04	nM	PMID[511322]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	15.74	nM	PMID[511322]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[511322]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	5482.77	nM	PMID[511322]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	397.19	nM	PMID[511322]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	5970.35	nM	PMID[511322]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	16330.52	nM	PMID[511322]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	9682.78	nM	PMID[511322]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	21037.78	nM	PMID[511322]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	19906.73	nM	PMID[511322]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	51286.14	nM	PMID[511322]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	17498.47	nM	PMID[511322]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	54450.27	nM	PMID[511322]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	1355.19	nM	PMID[511322]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	17498.47	nM	PMID[511322]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	3881.5	nM	PMID[511322]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	957.19	nM	PMID[511322]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	674.53	nM	PMID[511322]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	2454.71	nM	PMID[511322]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	28510.18	nM	PMID[511322]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	4570.88	nM	PMID[511322]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	5571.86	nM	PMID[511322]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	55462.57	nM	PMID[511322]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	10327.61	nM	PMID[511322]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	5152.29	nM	PMID[511322]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	5140.44	nM	PMID[511322]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	18967.06	nM	PMID[511322]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	11168.63	nM	PMID[511322]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	1923.09	nM	PMID[511322]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	7144.96	nM	PMID[511322]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	5662.39	nM	PMID[511322]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	16106.46	nM	PMID[511322]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	3303.7	nM	PMID[511322]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	83176.38	nM	PMID[511322]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	5140.44	nM	PMID[511322]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	653.13	nM	PMID[511322]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	1552.39	nM	PMID[511322]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[511322]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	17378.01	nM	PMID[511322]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	179.47	nM	PMID[511322]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	2213.09	nM	PMID[511322]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	40926.07	nM	PMID[511322]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	7464.49	nM	PMID[511322]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	2275.1	nM	PMID[511322]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	30060.76	nM	PMID[511322]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	8147.04	nM	PMID[511322]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	9506.05	nM	PMID[511322]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[511322]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[511322]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	3250.87	nM	PMID[511322]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1500.0	nM	PMID[511321]

☑ 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 NPC225051 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	403
0.1-0.2	1762
0.2-0.3	4055
0.3-0.4	11069
0.4-0.5	8054
0.5-0.6	6306
0.6-0.7	7283
0.7-0.8	3345
0.8-0.85	277
0.85-0.9	97
0.9-0.95	43
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC155211
0.9538	High Similarity	NPC80035
0.9466	High Similarity	NPC474813
0.9462	High Similarity	NPC50924
0.9449	High Similarity	NPC48248
0.9394	High Similarity	NPC245923
0.9375	High Similarity	NPC146647
0.9375	High Similarity	NPC34414
0.9333	High Similarity	NPC69755
0.9333	High Similarity	NPC239136
0.9333	High Similarity	NPC19631
0.9328	High Similarity	NPC96421
0.9323	High Similarity	NPC13715
0.9302	High Similarity	NPC55949
0.9297	High Similarity	NPC282923
0.9286	High Similarity	NPC142956
0.9259	High Similarity	NPC246638
0.9242	High Similarity	NPC283088
0.9231	High Similarity	NPC244699
0.9231	High Similarity	NPC474517
0.9231	High Similarity	NPC72669
0.9206	High Similarity	NPC375356
0.9154	High Similarity	NPC136588
0.9154	High Similarity	NPC199253
0.9127	High Similarity	NPC300274
0.9124	High Similarity	NPC471682
0.9091	High Similarity	NPC52407
0.9091	High Similarity	NPC115458
0.9091	High Similarity	NPC53896
0.9084	High Similarity	NPC205992
0.9077	High Similarity	NPC99731
0.9062	High Similarity	NPC103540
0.9051	High Similarity	NPC257644
0.9037	High Similarity	NPC4214
0.9023	High Similarity	NPC472262
0.9023	High Similarity	NPC287604
0.9023	High Similarity	NPC161964
0.9015	High Similarity	NPC58685
0.9015	High Similarity	NPC70622
0.9008	High Similarity	NPC31799
0.8993	High Similarity	NPC471683
0.8992	High Similarity	NPC160499
0.8992	High Similarity	NPC96915
0.8984	High Similarity	NPC173978
0.8976	High Similarity	NPC307174
0.8971	High Similarity	NPC242994
0.8971	High Similarity	NPC138099
0.8971	High Similarity	NPC26924
0.8963	High Similarity	NPC471905
0.8963	High Similarity	NPC53414
0.8963	High Similarity	NPC53206
0.8955	High Similarity	NPC258502
0.8921	High Similarity	NPC79627
0.8905	High Similarity	NPC315578
0.8905	High Similarity	NPC181560
0.8905	High Similarity	NPC169452
0.8897	High Similarity	NPC416
0.8897	High Similarity	NPC61398
0.8889	High Similarity	NPC254847
0.8889	High Similarity	NPC272268
0.8881	High Similarity	NPC288089
0.8865	High Similarity	NPC37709
0.8855	High Similarity	NPC96024
0.8849	High Similarity	NPC296752
0.8846	High Similarity	NPC3224
0.8828	High Similarity	NPC91478
0.8811	High Similarity	NPC205766
0.8806	High Similarity	NPC294226
0.8797	High Similarity	NPC93015
0.8794	High Similarity	NPC314437
0.8788	High Similarity	NPC276238
0.8777	High Similarity	NPC193555
0.8768	High Similarity	NPC225243
0.875	High Similarity	NPC120545
0.875	High Similarity	NPC193358
0.8741	High Similarity	NPC12070
0.8741	High Similarity	NPC44437
0.874	High Similarity	NPC206778
0.874	High Similarity	NPC285829
0.8732	High Similarity	NPC119767
0.8714	High Similarity	NPC451542
0.8714	High Similarity	NPC66593
0.8714	High Similarity	NPC313047
0.8714	High Similarity	NPC474203
0.8714	High Similarity	NPC53016
0.8714	High Similarity	NPC295712
0.8705	High Similarity	NPC305845
0.8705	High Similarity	NPC204045
0.8702	High Similarity	NPC231774
0.8702	High Similarity	NPC306765
0.8696	High Similarity	NPC143438
0.8696	High Similarity	NPC1268
0.8692	High Similarity	NPC310540
0.8686	High Similarity	NPC305060
0.8686	High Similarity	NPC62272
0.8676	High Similarity	NPC249272
0.8667	High Similarity	NPC314048
0.8667	High Similarity	NPC267205
0.8667	High Similarity	NPC114183
0.8662	High Similarity	NPC147250
0.8652	High Similarity	NPC21599
0.8652	High Similarity	NPC227841
0.8652	High Similarity	NPC10764
0.8652	High Similarity	NPC193703
0.8643	High Similarity	NPC469520
0.8643	High Similarity	NPC135524
0.8636	High Similarity	NPC69424
0.8636	High Similarity	NPC176130
0.8636	High Similarity	NPC78364
0.8636	High Similarity	NPC84672
0.8613	High Similarity	NPC191976
0.8603	High Similarity	NPC282780
0.8603	High Similarity	NPC270899
0.8603	High Similarity	NPC166480
0.8592	High Similarity	NPC12402
0.8582	High Similarity	NPC108129
0.8582	High Similarity	NPC293545
0.8582	High Similarity	NPC31539
0.8582	High Similarity	NPC174905
0.8582	High Similarity	NPC198305
0.8571	High Similarity	NPC66029
0.8571	High Similarity	NPC226656
0.8571	High Similarity	NPC124365
0.8571	High Similarity	NPC477275
0.8571	High Similarity	NPC66508
0.8561	High Similarity	NPC190457
0.8561	High Similarity	NPC254492
0.8552	High Similarity	NPC315520
0.8551	High Similarity	NPC53001
0.855	High Similarity	NPC164014
0.855	High Similarity	NPC68756
0.855	High Similarity	NPC199273
0.855	High Similarity	NPC236189
0.855	High Similarity	NPC152525
0.854	High Similarity	NPC161632
0.8531	High Similarity	NPC110882
0.8531	High Similarity	NPC271944
0.8531	High Similarity	NPC85393
0.8531	High Similarity	NPC143685
0.8529	High Similarity	NPC171968
0.8529	High Similarity	NPC470406
0.8527	High Similarity	NPC472046
0.8521	High Similarity	NPC471906
0.8521	High Similarity	NPC48762
0.8521	High Similarity	NPC244691
0.8519	High Similarity	NPC17083
0.8511	High Similarity	NPC85310
0.8511	High Similarity	NPC73061
0.8507	High Similarity	NPC278928
0.8496	Intermediate Similarity	NPC471530
0.8496	Intermediate Similarity	NPC72667
0.8493	Intermediate Similarity	NPC35
0.8492	Intermediate Similarity	NPC161304
0.8489	Intermediate Similarity	NPC87723
0.8478	Intermediate Similarity	NPC315275
0.8478	Intermediate Similarity	NPC474311
0.8478	Intermediate Similarity	NPC141934
0.8478	Intermediate Similarity	NPC472308
0.8472	Intermediate Similarity	NPC478018
0.8472	Intermediate Similarity	NPC290194
0.8467	Intermediate Similarity	NPC202225
0.8462	Intermediate Similarity	NPC478019
0.8462	Intermediate Similarity	NPC34482
0.8456	Intermediate Similarity	NPC309430
0.8446	Intermediate Similarity	NPC318270
0.8444	Intermediate Similarity	NPC27659
0.8444	Intermediate Similarity	NPC117609
0.844	Intermediate Similarity	NPC290550
0.8433	Intermediate Similarity	NPC237225
0.8433	Intermediate Similarity	NPC234175
0.8429	Intermediate Similarity	NPC470407
0.8425	Intermediate Similarity	NPC477453
0.8425	Intermediate Similarity	NPC108288
0.8417	Intermediate Similarity	NPC147418
0.8417	Intermediate Similarity	NPC44960
0.8417	Intermediate Similarity	NPC474110
0.8417	Intermediate Similarity	NPC36868
0.8409	Intermediate Similarity	NPC234890
0.8409	Intermediate Similarity	NPC74507
0.8406	Intermediate Similarity	NPC153088
0.8403	Intermediate Similarity	NPC285122
0.8403	Intermediate Similarity	NPC470570
0.8403	Intermediate Similarity	NPC300540
0.84	Intermediate Similarity	NPC324736
0.8397	Intermediate Similarity	NPC176208
0.8397	Intermediate Similarity	NPC282577
0.8382	Intermediate Similarity	NPC471851
0.8382	Intermediate Similarity	NPC85342
0.8382	Intermediate Similarity	NPC41847
0.838	Intermediate Similarity	NPC474961
0.8378	Intermediate Similarity	NPC182921
0.8378	Intermediate Similarity	NPC474824
0.8378	Intermediate Similarity	NPC218870
0.8378	Intermediate Similarity	NPC470408
0.837	Intermediate Similarity	NPC171460
0.837	Intermediate Similarity	NPC109123
0.837	Intermediate Similarity	NPC57552
0.837	Intermediate Similarity	NPC303910
0.8369	Intermediate Similarity	NPC203063
0.8345	Intermediate Similarity	NPC289042

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 NPC225051 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	964
0.2-0.3	1290
0.3-0.4	2780
0.4-0.5	2206
0.5-0.6	1066
0.6-0.7	369
0.7-0.8	82
0.8-0.85	2
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9062	High Similarity	NPD1470	Approved
0.8889	High Similarity	NPD1509	Clinical (unspecified phase)
0.875	High Similarity	NPD1201	Approved
0.8686	High Similarity	NPD5406	Approved
0.8686	High Similarity	NPD5405	Approved
0.8686	High Similarity	NPD5408	Approved
0.8686	High Similarity	NPD5404	Approved
0.8652	High Similarity	NPD7390	Discontinued
0.8425	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD3226	Approved
0.8099	Intermediate Similarity	NPD2346	Discontinued
0.7857	Intermediate Similarity	NPD2342	Discontinued
0.7847	Intermediate Similarity	NPD2344	Approved
0.781	Intermediate Similarity	NPD1164	Approved
0.7808	Intermediate Similarity	NPD7003	Approved
0.7801	Intermediate Similarity	NPD943	Approved
0.7771	Intermediate Similarity	NPD6232	Discontinued
0.7736	Intermediate Similarity	NPD7473	Discontinued
0.7707	Intermediate Similarity	NPD6959	Discontinued
0.7703	Intermediate Similarity	NPD3300	Phase 2
0.7635	Intermediate Similarity	NPD2309	Approved
0.763	Intermediate Similarity	NPD3019	Approved
0.7576	Intermediate Similarity	NPD5951	Approved
0.7556	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3764	Approved
0.7535	Intermediate Similarity	NPD2313	Discontinued
0.7534	Intermediate Similarity	NPD2935	Discontinued
0.7516	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2932	Approved
0.7483	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2799	Discontinued
0.7466	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1607	Approved
0.7424	Intermediate Similarity	NPD7635	Approved
0.7405	Intermediate Similarity	NPD3749	Approved
0.7403	Intermediate Similarity	NPD7458	Discontinued
0.7365	Intermediate Similarity	NPD1471	Phase 3
0.7347	Intermediate Similarity	NPD1510	Phase 2
0.7343	Intermediate Similarity	NPD7008	Discontinued
0.7325	Intermediate Similarity	NPD7819	Suspended
0.731	Intermediate Similarity	NPD1240	Approved
0.7294	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7177	Discontinued
0.7255	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD9266	Approved
0.7252	Intermediate Similarity	NPD74	Approved
0.7239	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1283	Approved
0.7233	Intermediate Similarity	NPD7768	Phase 2
0.7214	Intermediate Similarity	NPD4878	Approved
0.7209	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD9493	Approved
0.7202	Intermediate Similarity	NPD8313	Approved
0.7202	Intermediate Similarity	NPD8312	Approved
0.7197	Intermediate Similarity	NPD7411	Suspended
0.7194	Intermediate Similarity	NPD3026	Approved
0.7194	Intermediate Similarity	NPD3023	Approved
0.7176	Intermediate Similarity	NPD9263	Approved
0.7176	Intermediate Similarity	NPD8150	Discontinued
0.7176	Intermediate Similarity	NPD9267	Approved
0.7176	Intermediate Similarity	NPD9264	Approved
0.7174	Intermediate Similarity	NPD3025	Approved
0.7174	Intermediate Similarity	NPD1651	Approved
0.7174	Intermediate Similarity	NPD3024	Approved
0.7143	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2532	Approved
0.7134	Intermediate Similarity	NPD4380	Phase 2
0.7133	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2286	Discontinued
0.7108	Intermediate Similarity	NPD5844	Phase 1
0.7107	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3750	Approved
0.7105	Intermediate Similarity	NPD8166	Discontinued
0.7092	Intermediate Similarity	NPD3972	Approved
0.7086	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1549	Phase 2
0.7069	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6213	Phase 3
0.7069	Intermediate Similarity	NPD6212	Phase 3
0.7063	Intermediate Similarity	NPD2296	Approved
0.7063	Intermediate Similarity	NPD1203	Approved
0.7054	Intermediate Similarity	NPD1932	Approved
0.7029	Intermediate Similarity	NPD6534	Approved
0.7029	Intermediate Similarity	NPD6535	Approved
0.7021	Intermediate Similarity	NPD1281	Approved
0.7021	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD288	Approved
0.7	Intermediate Similarity	NPD1930	Approved
0.7	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4308	Phase 3
0.7	Intermediate Similarity	NPD1929	Approved
0.6993	Remote Similarity	NPD1876	Approved
0.6987	Remote Similarity	NPD6273	Approved
0.6986	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1511	Approved
0.6963	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD411	Approved
0.6937	Remote Similarity	NPD1934	Approved
0.6934	Remote Similarity	NPD9281	Approved
0.6934	Remote Similarity	NPD497	Approved
0.6929	Remote Similarity	NPD844	Approved
0.6927	Remote Similarity	NPD6777	Approved
0.6927	Remote Similarity	NPD6779	Approved
0.6927	Remote Similarity	NPD6776	Approved
0.6927	Remote Similarity	NPD6778	Approved
0.6927	Remote Similarity	NPD6781	Approved
0.6927	Remote Similarity	NPD6782	Approved
0.6927	Remote Similarity	NPD6780	Approved
0.6923	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7699	Phase 2
0.691	Remote Similarity	NPD7700	Phase 2
0.6894	Remote Similarity	NPD2801	Approved
0.6892	Remote Similarity	NPD6663	Approved
0.6883	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1512	Approved
0.6879	Remote Similarity	NPD4626	Approved
0.6879	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7075	Discontinued
0.687	Remote Similarity	NPD9261	Approved
0.6868	Remote Similarity	NPD7871	Phase 2
0.6868	Remote Similarity	NPD7870	Phase 2
0.6866	Remote Similarity	NPD2329	Discontinued
0.6866	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD496	Approved
0.6861	Remote Similarity	NPD498	Approved
0.6861	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD495	Approved
0.6853	Remote Similarity	NPD9717	Approved
0.6849	Remote Similarity	NPD5736	Approved
0.6842	Remote Similarity	NPD2796	Approved
0.6842	Remote Similarity	NPD1551	Phase 2
0.6842	Remote Similarity	NPD6099	Approved
0.6842	Remote Similarity	NPD6100	Approved
0.6831	Remote Similarity	NPD4879	Approved
0.6826	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6166	Phase 2
0.6826	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3268	Approved
0.6818	Remote Similarity	NPD2800	Approved
0.6818	Remote Similarity	NPD1237	Approved
0.6813	Remote Similarity	NPD7696	Phase 3
0.6813	Remote Similarity	NPD7435	Discontinued
0.6813	Remote Similarity	NPD7698	Approved
0.6813	Remote Similarity	NPD7697	Approved
0.681	Remote Similarity	NPD3882	Suspended
0.6806	Remote Similarity	NPD1755	Approved
0.6805	Remote Similarity	NPD6020	Phase 2
0.68	Remote Similarity	NPD447	Suspended
0.679	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5494	Approved
0.6786	Remote Similarity	NPD7610	Discontinued
0.6784	Remote Similarity	NPD5029	Approved
0.6784	Remote Similarity	NPD5027	Approved
0.6784	Remote Similarity	NPD5031	Approved
0.6784	Remote Similarity	NPD6559	Discontinued
0.6776	Remote Similarity	NPD8319	Approved
0.6776	Remote Similarity	NPD8320	Phase 1
0.6776	Remote Similarity	NPD3748	Approved
0.6774	Remote Similarity	NPD4628	Phase 3
0.6769	Remote Similarity	NPD3020	Approved
0.6765	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4625	Phase 3
0.6748	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5026	Approved
0.6744	Remote Similarity	NPD4955	Approved
0.6744	Remote Similarity	NPD5034	Approved
0.6744	Remote Similarity	NPD36	Approved
0.6744	Remote Similarity	NPD5028	Approved
0.6744	Remote Similarity	NPD4954	Approved
0.6738	Remote Similarity	NPD9545	Approved
0.6738	Remote Similarity	NPD3091	Approved
0.6736	Remote Similarity	NPD1608	Approved
0.6733	Remote Similarity	NPD2979	Phase 3
0.6733	Remote Similarity	NPD4307	Phase 2
0.6728	Remote Similarity	NPD6844	Discontinued
0.672	Remote Similarity	NPD8151	Discontinued
0.6718	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2797	Approved
0.6708	Remote Similarity	NPD6599	Discontinued
0.6707	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD4750	Phase 3
0.6691	Remote Similarity	NPD3022	Approved
0.6691	Remote Similarity	NPD3021	Approved
0.669	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6832	Phase 2
0.6689	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1465	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