NPASS Compound

Structure

NPC264922 OpenBabel07101719142D 23 25 0 0 0 0 0 0 0 0999 V2000 -0.8660 3.5000 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 -3.4641 -0.0000 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 1.7321 2.0000 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 -1.7321 2.0000 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 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 1.7321 -0.0000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 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 3.4641 0.0000 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 -0.0000 3.0000 0.0000 O 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 1 23 1 0 0 0 0 2 6 2 0 0 0 0 2 7 1 0 0 0 0 3 6 1 0 0 0 0 3 10 2 0 0 0 0 4 8 2 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 5 18 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 14 2 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 16 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 17 1 0 0 0 0 15 21 2 0 0 0 0 16 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.02
Volume:	306.484
LogP:	4.044
LogD:	2.674
LogS:	-4.148
# Rotatable Bonds:	2
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	2.922
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.153
MDCK Permeability:	6.31359534963849e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.328
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	97.17243194580078%
Volume Distribution (VD):	0.487
Pgp-substrate:	6.038589954376221%

ADMET: Metabolism

CYP1A2-inhibitor:	0.88
CYP1A2-substrate:	0.661
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.599
CYP2C9-substrate:	0.616
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.074
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	5.26
Half-life (T1/2):	0.782

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.794
AMES Toxicity:	0.439
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.873
Carcinogencity:	0.039
Eye Corrosion:	0.239
Eye Irritation:	0.938
Respiratory Toxicity:	0.785

Download Data

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

Natural Product: NPC264922

Natural Product ID:	NPC264922
*Common Name:**	5-Chloro-Omega-Hydroxy-1-O-Methylemodin
IUPAC Name:	1-chloro-2,4-dihydroxy-7-(hydroxymethyl)-5-methoxyanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	GFNBQXKNWQSVTJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H11ClO6/c1-23-10-3-6(5-18)2-7-11(10)16(22)12-8(19)4-9(20)14(17)13(12)15(7)21/h2-4,18-20H,5H2,1H3
SMILES:	OCc1cc(OC)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1Cl)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1643638
PubChem CID:	53319344
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]

☑ 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
MIC	1

Activity Type	# Activity
Cell Line	3
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	40100.0	nM	PMID[516274]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	28400.0	nM	PMID[516274]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	22000.0	nM	PMID[516274]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	MIC	=	18710.0	nM	PMID[516274]
NPT2	Others	Unspecified		IC50	=	16000.0	nM	PMID[516274]

☑ 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 NPC264922 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	469
0.1-0.2	2138
0.2-0.3	5274
0.3-0.4	12518
0.4-0.5	5592
0.5-0.6	5713
0.6-0.7	6205
0.7-0.8	4545
0.8-0.85	170
0.85-0.9	59
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9815	High Similarity	NPC277865
0.9755	High Similarity	NPC474857
0.9281	High Similarity	NPC470560
0.9226	High Similarity	NPC470422
0.9222	High Similarity	NPC470562
0.9222	High Similarity	NPC470565
0.9133	High Similarity	NPC191606
0.8976	High Similarity	NPC470561
0.896	High Similarity	NPC151292
0.8922	High Similarity	NPC470563
0.8895	High Similarity	NPC45072
0.8827	High Similarity	NPC147735
0.8795	High Similarity	NPC470559
0.8712	High Similarity	NPC255641
0.8712	High Similarity	NPC290954
0.8708	High Similarity	NPC316091
0.8708	High Similarity	NPC313386
0.8686	High Similarity	NPC306240
0.8675	High Similarity	NPC470564
0.8659	High Similarity	NPC470569
0.8655	High Similarity	NPC472032
0.8642	High Similarity	NPC126767
0.8642	High Similarity	NPC190648
0.8642	High Similarity	NPC312929
0.8642	High Similarity	NPC289042
0.8642	High Similarity	NPC245584
0.8642	High Similarity	NPC118027
0.8642	High Similarity	NPC56433
0.8598	High Similarity	NPC470568
0.8598	High Similarity	NPC294646
0.8547	High Similarity	NPC474499
0.8525	High Similarity	NPC313541
0.8494	Intermediate Similarity	NPC154683
0.8494	Intermediate Similarity	NPC40356
0.848	Intermediate Similarity	NPC470081
0.8462	Intermediate Similarity	NPC220369
0.8462	Intermediate Similarity	NPC324736
0.8457	Intermediate Similarity	NPC19896
0.8443	Intermediate Similarity	NPC208806
0.8432	Intermediate Similarity	NPC154720
0.843	Intermediate Similarity	NPC68850
0.8421	Intermediate Similarity	NPC473696
0.8415	Intermediate Similarity	NPC214901
0.8409	Intermediate Similarity	NPC477568
0.8402	Intermediate Similarity	NPC197326
0.8382	Intermediate Similarity	NPC28669
0.8373	Intermediate Similarity	NPC202595
0.8363	Intermediate Similarity	NPC298401
0.8344	Intermediate Similarity	NPC193703
0.8344	Intermediate Similarity	NPC48762
0.8344	Intermediate Similarity	NPC21599
0.8343	Intermediate Similarity	NPC280497
0.8333	Intermediate Similarity	NPC107109
0.8324	Intermediate Similarity	NPC173352
0.8324	Intermediate Similarity	NPC58653
0.8314	Intermediate Similarity	NPC474096
0.8303	Intermediate Similarity	NPC34802
0.8293	Intermediate Similarity	NPC34482
0.8293	Intermediate Similarity	NPC49282
0.8284	Intermediate Similarity	NPC66508
0.8284	Intermediate Similarity	NPC226656
0.8282	Intermediate Similarity	NPC167663
0.8276	Intermediate Similarity	NPC474061
0.8261	Intermediate Similarity	NPC221185
0.8253	Intermediate Similarity	NPC2569
0.8253	Intermediate Similarity	NPC172329
0.8251	Intermediate Similarity	NPC470100
0.8251	Intermediate Similarity	NPC470099
0.8242	Intermediate Similarity	NPC470570
0.8242	Intermediate Similarity	NPC300540
0.8235	Intermediate Similarity	NPC77807
0.8235	Intermediate Similarity	NPC14561
0.8235	Intermediate Similarity	NPC5379
0.8232	Intermediate Similarity	NPC99937
0.8226	Intermediate Similarity	NPC198163
0.8225	Intermediate Similarity	NPC214632
0.8221	Intermediate Similarity	NPC94076
0.8221	Intermediate Similarity	NPC182255
0.8216	Intermediate Similarity	NPC247104
0.8214	Intermediate Similarity	NPC478148
0.8214	Intermediate Similarity	NPC474417
0.8214	Intermediate Similarity	NPC149526
0.8208	Intermediate Similarity	NPC245122
0.8204	Intermediate Similarity	NPC329933
0.8198	Intermediate Similarity	NPC470342
0.8198	Intermediate Similarity	NPC84571
0.8198	Intermediate Similarity	NPC472052
0.8198	Intermediate Similarity	NPC472060
0.8193	Intermediate Similarity	NPC477569
0.8187	Intermediate Similarity	NPC199463
0.8187	Intermediate Similarity	NPC263483
0.8187	Intermediate Similarity	NPC37543
0.8187	Intermediate Similarity	NPC472404
0.8187	Intermediate Similarity	NPC178976
0.8182	Intermediate Similarity	NPC478019
0.8171	Intermediate Similarity	NPC84266
0.8167	Intermediate Similarity	NPC471801
0.8166	Intermediate Similarity	NPC51824
0.8166	Intermediate Similarity	NPC470337
0.8166	Intermediate Similarity	NPC180944
0.8166	Intermediate Similarity	NPC470338
0.8166	Intermediate Similarity	NPC113608
0.8166	Intermediate Similarity	NPC470340
0.8166	Intermediate Similarity	NPC268992
0.816	Intermediate Similarity	NPC305845
0.816	Intermediate Similarity	NPC204045
0.815	Intermediate Similarity	NPC311740
0.8148	Intermediate Similarity	NPC190457
0.8144	Intermediate Similarity	NPC256672
0.8144	Intermediate Similarity	NPC27221
0.8144	Intermediate Similarity	NPC7025
0.8144	Intermediate Similarity	NPC472056
0.8136	Intermediate Similarity	NPC474004
0.8125	Intermediate Similarity	NPC324522
0.8125	Intermediate Similarity	NPC234497
0.8125	Intermediate Similarity	NPC105414
0.8125	Intermediate Similarity	NPC472058
0.8125	Intermediate Similarity	NPC470341
0.8121	Intermediate Similarity	NPC244691
0.8121	Intermediate Similarity	NPC471906
0.8121	Intermediate Similarity	NPC475201
0.8118	Intermediate Similarity	NPC93552
0.8118	Intermediate Similarity	NPC135522
0.8118	Intermediate Similarity	NPC155686
0.811	Intermediate Similarity	NPC135524
0.811	Intermediate Similarity	NPC49108
0.8107	Intermediate Similarity	NPC232645
0.8107	Intermediate Similarity	NPC72958
0.8107	Intermediate Similarity	NPC46882
0.8107	Intermediate Similarity	NPC132990
0.8107	Intermediate Similarity	NPC230848
0.8095	Intermediate Similarity	NPC65589
0.8095	Intermediate Similarity	NPC108744
0.8095	Intermediate Similarity	NPC477566
0.8095	Intermediate Similarity	NPC158338
0.8095	Intermediate Similarity	NPC100985
0.8095	Intermediate Similarity	NPC288036
0.8095	Intermediate Similarity	NPC97028
0.8095	Intermediate Similarity	NPC97029
0.8095	Intermediate Similarity	NPC80370
0.8095	Intermediate Similarity	NPC477567
0.8092	Intermediate Similarity	NPC284495
0.8092	Intermediate Similarity	NPC470810
0.809	Intermediate Similarity	NPC188618
0.8084	Intermediate Similarity	NPC71055
0.8084	Intermediate Similarity	NPC7943
0.8084	Intermediate Similarity	NPC123202
0.8084	Intermediate Similarity	NPC22005
0.8075	Intermediate Similarity	NPC48822
0.8072	Intermediate Similarity	NPC28632
0.807	Intermediate Similarity	NPC68727
0.8059	Intermediate Similarity	NPC175978
0.8059	Intermediate Similarity	NPC87708
0.8059	Intermediate Similarity	NPC273483
0.8057	Intermediate Similarity	NPC100849
0.8057	Intermediate Similarity	NPC101769
0.8049	Intermediate Similarity	NPC253822
0.8049	Intermediate Similarity	NPC101366
0.8047	Intermediate Similarity	NPC119929
0.8047	Intermediate Similarity	NPC225854
0.8046	Intermediate Similarity	NPC472405
0.8037	Intermediate Similarity	NPC1268
0.8032	Intermediate Similarity	NPC193676
0.8025	Intermediate Similarity	NPC471905
0.8024	Intermediate Similarity	NPC163846
0.8024	Intermediate Similarity	NPC225173
0.8023	Intermediate Similarity	NPC180924
0.8023	Intermediate Similarity	NPC146211
0.8012	Intermediate Similarity	NPC51887
0.8012	Intermediate Similarity	NPC117836
0.8012	Intermediate Similarity	NPC476178
0.8012	Intermediate Similarity	NPC475705
0.8012	Intermediate Similarity	NPC210942
0.8012	Intermediate Similarity	NPC169990
0.8012	Intermediate Similarity	NPC329844
0.8011	Intermediate Similarity	NPC472606
0.8011	Intermediate Similarity	NPC472057
0.8011	Intermediate Similarity	NPC73544
0.8011	Intermediate Similarity	NPC472051
0.8	Intermediate Similarity	NPC52789
0.8	Intermediate Similarity	NPC470087
0.8	Intermediate Similarity	NPC268204
0.8	Intermediate Similarity	NPC258249
0.8	Intermediate Similarity	NPC39819
0.8	Intermediate Similarity	NPC321980
0.8	Intermediate Similarity	NPC469404
0.8	Intermediate Similarity	NPC26051
0.8	Intermediate Similarity	NPC55832
0.8	Intermediate Similarity	NPC474961
0.7989	Intermediate Similarity	NPC111536
0.7989	Intermediate Similarity	NPC5029
0.7989	Intermediate Similarity	NPC271385
0.7989	Intermediate Similarity	NPC470103
0.7989	Intermediate Similarity	NPC76128
0.7989	Intermediate Similarity	NPC30432
0.7988	Intermediate Similarity	NPC295384
0.7988	Intermediate Similarity	NPC472366
0.7988	Intermediate Similarity	NPC65775
0.7988	Intermediate Similarity	NPC10027
0.7978	Intermediate Similarity	NPC184518

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 NPC264922 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	440
0.1-0.2	1074
0.2-0.3	1906
0.3-0.4	2866
0.4-0.5	1723
0.5-0.6	819
0.6-0.7	255
0.7-0.8	67
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7963	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6232	Discontinued
0.7865	Intermediate Similarity	NPD7473	Discontinued
0.7841	Intermediate Similarity	NPD6959	Discontinued
0.7751	Intermediate Similarity	NPD2532	Approved
0.7751	Intermediate Similarity	NPD2534	Approved
0.7751	Intermediate Similarity	NPD2533	Approved
0.7744	Intermediate Similarity	NPD1510	Phase 2
0.773	Intermediate Similarity	NPD1607	Approved
0.7701	Intermediate Similarity	NPD7819	Suspended
0.7647	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD4380	Phase 2
0.7611	Intermediate Similarity	NPD2403	Approved
0.7607	Intermediate Similarity	NPD1240	Approved
0.76	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1549	Phase 2
0.7487	Intermediate Similarity	NPD4363	Phase 3
0.7487	Intermediate Similarity	NPD4360	Phase 2
0.7485	Intermediate Similarity	NPD7390	Discontinued
0.7458	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD1934	Approved
0.7442	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5844	Phase 1
0.7386	Intermediate Similarity	NPD7411	Suspended
0.7358	Intermediate Similarity	NPD4361	Phase 2
0.7358	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2801	Approved
0.7292	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1511	Approved
0.7278	Intermediate Similarity	NPD7075	Discontinued
0.7278	Intermediate Similarity	NPD3749	Approved
0.7278	Intermediate Similarity	NPD2796	Approved
0.7278	Intermediate Similarity	NPD2935	Discontinued
0.7251	Intermediate Similarity	NPD2800	Approved
0.7235	Intermediate Similarity	NPD2346	Discontinued
0.7228	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6166	Phase 2
0.7228	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7768	Phase 2
0.7222	Intermediate Similarity	NPD3882	Suspended
0.7213	Intermediate Similarity	NPD5711	Approved
0.7213	Intermediate Similarity	NPD5710	Approved
0.7209	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3750	Approved
0.7207	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1512	Approved
0.7198	Intermediate Similarity	NPD5494	Approved
0.7182	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6559	Discontinued
0.7178	Intermediate Similarity	NPD1470	Approved
0.7151	Intermediate Similarity	NPD6801	Discontinued
0.7151	Intermediate Similarity	NPD3818	Discontinued
0.7135	Intermediate Similarity	NPD6599	Discontinued
0.7127	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1551	Phase 2
0.7072	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6780	Approved
0.7035	Intermediate Similarity	NPD6776	Approved
0.7035	Intermediate Similarity	NPD6777	Approved
0.7035	Intermediate Similarity	NPD6779	Approved
0.7035	Intermediate Similarity	NPD6781	Approved
0.7035	Intermediate Similarity	NPD6778	Approved
0.7035	Intermediate Similarity	NPD6782	Approved
0.7022	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8151	Discontinued
0.7	Intermediate Similarity	NPD6651	Approved
0.6989	Remote Similarity	NPD6799	Approved
0.6984	Remote Similarity	NPD7074	Phase 3
0.6982	Remote Similarity	NPD943	Approved
0.6978	Remote Similarity	NPD3817	Phase 2
0.6977	Remote Similarity	NPD5408	Approved
0.6977	Remote Similarity	NPD5404	Approved
0.6977	Remote Similarity	NPD5406	Approved
0.6977	Remote Similarity	NPD5405	Approved
0.6977	Remote Similarity	NPD6100	Approved
0.6977	Remote Similarity	NPD6099	Approved
0.6966	Remote Similarity	NPD920	Approved
0.6961	Remote Similarity	NPD37	Approved
0.6949	Remote Similarity	NPD1578	Phase 2
0.6947	Remote Similarity	NPD5953	Discontinued
0.6936	Remote Similarity	NPD2344	Approved
0.6933	Remote Similarity	NPD1201	Approved
0.6931	Remote Similarity	NPD7697	Approved
0.6931	Remote Similarity	NPD7698	Approved
0.6931	Remote Similarity	NPD7696	Phase 3
0.6931	Remote Similarity	NPD7435	Discontinued
0.6931	Remote Similarity	NPD7054	Approved
0.6927	Remote Similarity	NPD8312	Approved
0.6927	Remote Similarity	NPD8313	Approved
0.6923	Remote Similarity	NPD1465	Phase 2
0.6923	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3748	Approved
0.6897	Remote Similarity	NPD7870	Phase 2
0.6897	Remote Similarity	NPD7871	Phase 2
0.6895	Remote Similarity	NPD7472	Approved
0.6889	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5402	Approved
0.6878	Remote Similarity	NPD3751	Discontinued
0.6875	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6797	Phase 2
0.6859	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1243	Approved
0.6854	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4967	Phase 2
0.6848	Remote Similarity	NPD4966	Approved
0.6848	Remote Similarity	NPD4965	Approved
0.6842	Remote Similarity	NPD7286	Phase 2
0.6823	Remote Similarity	NPD7251	Discontinued
0.6821	Remote Similarity	NPD2799	Discontinued
0.6821	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8150	Discontinued
0.6818	Remote Similarity	NPD4628	Phase 3
0.6818	Remote Similarity	NPD7003	Approved
0.6818	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7041	Phase 2
0.6796	Remote Similarity	NPD7458	Discontinued
0.6796	Remote Similarity	NPD7701	Phase 2
0.6791	Remote Similarity	NPD1247	Approved
0.6788	Remote Similarity	NPD7808	Phase 3
0.6788	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6535	Approved
0.6784	Remote Similarity	NPD6534	Approved
0.678	Remote Similarity	NPD2309	Approved
0.6774	Remote Similarity	NPD6234	Discontinued
0.6765	Remote Similarity	NPD2313	Discontinued
0.6755	Remote Similarity	NPD7229	Phase 3
0.6744	Remote Similarity	NPD230	Phase 1
0.6742	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7874	Approved
0.6731	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD958	Approved
0.672	Remote Similarity	NPD3926	Phase 2
0.6716	Remote Similarity	NPD6823	Phase 2
0.6706	Remote Similarity	NPD4625	Phase 3
0.67	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7801	Approved
0.6685	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5403	Approved
0.6684	Remote Similarity	NPD919	Approved
0.6683	Remote Similarity	NPD7700	Phase 2
0.6683	Remote Similarity	NPD7699	Phase 2
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD957	Approved
0.6648	Remote Similarity	NPD1471	Phase 3
0.6627	Remote Similarity	NPD2798	Approved
0.6615	Remote Similarity	NPD7177	Discontinued
0.6615	Remote Similarity	NPD7228	Approved
0.6607	Remote Similarity	NPD1283	Approved
0.6597	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD2354	Approved
0.6587	Remote Similarity	NPD3972	Approved
0.6579	Remote Similarity	NPD3787	Discontinued
0.6571	Remote Similarity	NPD4538	Approved
0.6571	Remote Similarity	NPD4536	Approved
0.6571	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.657	Remote Similarity	NPD8319	Approved
0.657	Remote Similarity	NPD8320	Phase 1
0.6567	Remote Similarity	NPD6212	Phase 3
0.6567	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6213	Phase 3
0.6566	Remote Similarity	NPD8434	Phase 2
0.6559	Remote Similarity	NPD5761	Phase 2
0.6559	Remote Similarity	NPD5760	Phase 2
0.6552	Remote Similarity	NPD1184	Approved
0.655	Remote Similarity	NPD4908	Phase 1
0.6545	Remote Similarity	NPD1651	Approved
0.654	Remote Similarity	NPD7783	Phase 2
0.654	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6273	Approved
0.6538	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD4914	Approved
0.6529	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7199	Phase 2
0.6517	Remote Similarity	NPD3819	Phase 2
0.6515	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD1876	Approved
0.65	Remote Similarity	NPD4287	Approved
0.65	Remote Similarity	NPD3887	Approved
0.6491	Remote Similarity	NPD454	Approved
0.648	Remote Similarity	NPD2654	Approved
0.6474	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1203	Approved
0.6463	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD2353	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