NPASS Compound

Structure

NPC474902 OpenBabel07101719122D 26 28 0 0 0 0 0 0 0 0999 V2000 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -1.0000 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 -0.8660 -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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 N 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 21 2 0 0 0 0 14 18 2 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 24 2 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 18 25 1 0 0 0 0 19 20 2 3 0 0 0 19 22 1 0 0 0 0 19 26 1 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	367.1
Volume:	363.016
LogP:	3.434
LogD:	3.192
LogS:	-4.055
# Rotatable Bonds:	6
TPSA:	86.86
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.284
Synthetic Accessibility Score:	2.499
Fsp3:	0.105
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.165
MDCK Permeability:	1.3315112482814584e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.167
20% Bioavailability (F20%):	0.111
30% Bioavailability (F30%):	0.797

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	99.9532241821289%
Volume Distribution (VD):	0.377
Pgp-substrate:	0.7321823239326477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.643
CYP2C19-inhibitor:	0.92
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.905
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.521
CYP2D6-substrate:	0.801
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	4.55
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.668
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.796
Rat Oral Acute Toxicity:	0.78
Maximum Recommended Daily Dose:	0.09
Skin Sensitization:	0.267
Carcinogencity:	0.817
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC474902

Natural Product ID:	NPC474902
*Common Name:**	TZNWZBKFXRXPNE-CIAFOILYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TZNWZBKFXRXPNE-CIAFOILYSA-N
Standard InCHI:	InChI=1S/C19H17N3O3S/c1-12(21-22-19(26)20-11-13-5-3-2-4-6-13)17-15(23)9-7-14-8-10-16(24)25-18(14)17/h2-10,23H,11H2,1H3,(H2,20,22,26)/b21-12+
SMILES:	SC(=NCc1ccccc1)N/N=C(/c1c(O)ccc2c1oc(=O)cc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486900
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0002908] Hydroxycoumarins [CHEMONTID:0002909] 7-hydroxycoumarins

*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
NPO33433	adina cordifolia	Species	Rubiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[18675491]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1635	Cell Line	H9c2	Rattus norvegicus	Activity	>	80.0	%	PMID[555541]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	1060000.0	nM	PMID[555541]

☑ 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 NPC474902 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	299
0.1-0.2	2052
0.2-0.3	7578
0.3-0.4	10257
0.4-0.5	6325
0.5-0.6	9345
0.6-0.7	5801
0.7-0.8	1035
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9152	High Similarity	NPC474919
0.8812	High Similarity	NPC473778
0.8631	High Similarity	NPC474881
0.8371	Intermediate Similarity	NPC475411
0.7673	Intermediate Similarity	NPC32463
0.7595	Intermediate Similarity	NPC243688
0.7485	Intermediate Similarity	NPC131950
0.7468	Intermediate Similarity	NPC244495
0.7468	Intermediate Similarity	NPC93219
0.7358	Intermediate Similarity	NPC168259
0.7337	Intermediate Similarity	NPC314025
0.7321	Intermediate Similarity	NPC183642
0.7321	Intermediate Similarity	NPC310370
0.7232	Intermediate Similarity	NPC206736
0.7232	Intermediate Similarity	NPC195766
0.7222	Intermediate Similarity	NPC185066
0.7219	Intermediate Similarity	NPC170812
0.7215	Intermediate Similarity	NPC52247
0.7212	Intermediate Similarity	NPC31849
0.7204	Intermediate Similarity	NPC314213
0.7204	Intermediate Similarity	NPC314656
0.7193	Intermediate Similarity	NPC471824
0.7188	Intermediate Similarity	NPC201667
0.7188	Intermediate Similarity	NPC291899
0.7188	Intermediate Similarity	NPC73413
0.717	Intermediate Similarity	NPC96286
0.717	Intermediate Similarity	NPC248429
0.7166	Intermediate Similarity	NPC315913
0.716	Intermediate Similarity	NPC71903
0.7152	Intermediate Similarity	NPC194277
0.7151	Intermediate Similarity	NPC71739
0.7151	Intermediate Similarity	NPC475719
0.7151	Intermediate Similarity	NPC43716
0.7151	Intermediate Similarity	NPC101255
0.7151	Intermediate Similarity	NPC295696
0.7125	Intermediate Similarity	NPC472518
0.7125	Intermediate Similarity	NPC109675
0.7125	Intermediate Similarity	NPC315807
0.7125	Intermediate Similarity	NPC273772
0.7108	Intermediate Similarity	NPC163557
0.7107	Intermediate Similarity	NPC187868
0.7101	Intermediate Similarity	NPC47040
0.7101	Intermediate Similarity	NPC144512
0.7101	Intermediate Similarity	NPC279573
0.7101	Intermediate Similarity	NPC137262
0.7101	Intermediate Similarity	NPC35501
0.7101	Intermediate Similarity	NPC278600
0.7101	Intermediate Similarity	NPC37428
0.7093	Intermediate Similarity	NPC313414
0.7091	Intermediate Similarity	NPC66430
0.7091	Intermediate Similarity	NPC37009
0.7089	Intermediate Similarity	NPC247553
0.7083	Intermediate Similarity	NPC26954
0.7083	Intermediate Similarity	NPC38099
0.7081	Intermediate Similarity	NPC27671
0.7081	Intermediate Similarity	NPC111347
0.7073	Intermediate Similarity	NPC474289
0.7066	Intermediate Similarity	NPC50896
0.7066	Intermediate Similarity	NPC204353
0.7066	Intermediate Similarity	NPC326600
0.7063	Intermediate Similarity	NPC257188
0.7063	Intermediate Similarity	NPC13007
0.7055	Intermediate Similarity	NPC258567
0.7055	Intermediate Similarity	NPC121740
0.7055	Intermediate Similarity	NPC224774
0.7048	Intermediate Similarity	NPC281558
0.7048	Intermediate Similarity	NPC19157
0.7044	Intermediate Similarity	NPC302107
0.7041	Intermediate Similarity	NPC474886
0.7037	Intermediate Similarity	NPC232692
0.7037	Intermediate Similarity	NPC471828
0.7037	Intermediate Similarity	NPC202594
0.7037	Intermediate Similarity	NPC471827
0.7018	Intermediate Similarity	NPC195357
0.7018	Intermediate Similarity	NPC152771
0.7012	Intermediate Similarity	NPC469453
0.7012	Intermediate Similarity	NPC157212
0.7012	Intermediate Similarity	NPC472519
0.7006	Intermediate Similarity	NPC83535
0.7	Intermediate Similarity	NPC151946
0.7	Intermediate Similarity	NPC211110
0.6994	Remote Similarity	NPC471826
0.6994	Remote Similarity	NPC36181
0.6994	Remote Similarity	NPC36732
0.6989	Remote Similarity	NPC276665
0.6989	Remote Similarity	NPC265473
0.6988	Remote Similarity	NPC250727
0.6975	Remote Similarity	NPC86502
0.6975	Remote Similarity	NPC106914
0.6975	Remote Similarity	NPC159132
0.6975	Remote Similarity	NPC246648
0.6975	Remote Similarity	NPC134195
0.6975	Remote Similarity	NPC197351
0.6971	Remote Similarity	NPC154217
0.697	Remote Similarity	NPC168710
0.6968	Remote Similarity	NPC327005
0.6964	Remote Similarity	NPC224475
0.6964	Remote Similarity	NPC213173
0.6964	Remote Similarity	NPC180716
0.6964	Remote Similarity	NPC62366
0.6959	Remote Similarity	NPC312881
0.6954	Remote Similarity	NPC470296
0.6954	Remote Similarity	NPC87609
0.6954	Remote Similarity	NPC188632
0.6954	Remote Similarity	NPC94794
0.6954	Remote Similarity	NPC196459
0.6954	Remote Similarity	NPC112791
0.6954	Remote Similarity	NPC86069
0.6951	Remote Similarity	NPC149796
0.6949	Remote Similarity	NPC103116
0.6946	Remote Similarity	NPC469956
0.6946	Remote Similarity	NPC307289
0.6944	Remote Similarity	NPC306366
0.6941	Remote Similarity	NPC131198
0.6941	Remote Similarity	NPC153818
0.6941	Remote Similarity	NPC281014
0.6941	Remote Similarity	NPC212124
0.6941	Remote Similarity	NPC225106
0.6941	Remote Similarity	NPC155963
0.6941	Remote Similarity	NPC294456
0.6941	Remote Similarity	NPC184861
0.6941	Remote Similarity	NPC232246
0.6937	Remote Similarity	NPC235190
0.6937	Remote Similarity	NPC180006
0.6935	Remote Similarity	NPC198075
0.6933	Remote Similarity	NPC103420
0.6933	Remote Similarity	NPC17809
0.6933	Remote Similarity	NPC102540
0.6933	Remote Similarity	NPC285040
0.6933	Remote Similarity	NPC188022
0.6932	Remote Similarity	NPC142863
0.6932	Remote Similarity	NPC180477
0.6928	Remote Similarity	NPC113098
0.6923	Remote Similarity	NPC204179
0.6923	Remote Similarity	NPC61499
0.6923	Remote Similarity	NPC472525
0.6919	Remote Similarity	NPC287286
0.6919	Remote Similarity	NPC155552
0.6919	Remote Similarity	NPC138149
0.6914	Remote Similarity	NPC469935
0.6914	Remote Similarity	NPC1886
0.6914	Remote Similarity	NPC154176
0.6914	Remote Similarity	NPC196137
0.6914	Remote Similarity	NPC178627
0.6914	Remote Similarity	NPC50720
0.6914	Remote Similarity	NPC290605
0.6914	Remote Similarity	NPC469953
0.6914	Remote Similarity	NPC173350
0.6909	Remote Similarity	NPC219923
0.6906	Remote Similarity	NPC22014
0.6905	Remote Similarity	NPC205797
0.6905	Remote Similarity	NPC472524
0.6905	Remote Similarity	NPC133956
0.6905	Remote Similarity	NPC241165
0.6905	Remote Similarity	NPC141822
0.6905	Remote Similarity	NPC469955
0.6905	Remote Similarity	NPC142563
0.6905	Remote Similarity	NPC185777
0.6905	Remote Similarity	NPC471910
0.6905	Remote Similarity	NPC207002
0.6905	Remote Similarity	NPC291551
0.6905	Remote Similarity	NPC469952
0.6905	Remote Similarity	NPC296624
0.6905	Remote Similarity	NPC318400
0.6905	Remote Similarity	NPC167111
0.6905	Remote Similarity	NPC1220
0.6901	Remote Similarity	NPC221046
0.6901	Remote Similarity	NPC332594
0.6897	Remote Similarity	NPC97282
0.6897	Remote Similarity	NPC17760
0.6894	Remote Similarity	NPC144418
0.689	Remote Similarity	NPC234109
0.689	Remote Similarity	NPC276212
0.689	Remote Similarity	NPC188327
0.6886	Remote Similarity	NPC29734
0.6886	Remote Similarity	NPC272650
0.6886	Remote Similarity	NPC267336
0.6882	Remote Similarity	NPC223616
0.6882	Remote Similarity	NPC188380
0.6882	Remote Similarity	NPC224543
0.6882	Remote Similarity	NPC78746
0.6879	Remote Similarity	NPC172986
0.6879	Remote Similarity	NPC20631
0.6879	Remote Similarity	NPC93640
0.6879	Remote Similarity	NPC475680
0.6879	Remote Similarity	NPC305355
0.6879	Remote Similarity	NPC270883
0.6879	Remote Similarity	NPC261227
0.6875	Remote Similarity	NPC470322
0.6875	Remote Similarity	NPC57470
0.6875	Remote Similarity	NPC181388
0.6875	Remote Similarity	NPC263835
0.6872	Remote Similarity	NPC476565
0.6871	Remote Similarity	NPC95733
0.6871	Remote Similarity	NPC140521
0.6871	Remote Similarity	NPC62101
0.6867	Remote Similarity	NPC134360
0.6864	Remote Similarity	NPC166672
0.6864	Remote Similarity	NPC100986
0.6864	Remote Similarity	NPC47163

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 NPC474902 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	715
0.2-0.3	1056
0.3-0.4	2070
0.4-0.5	3096
0.5-0.6	1675
0.6-0.7	323
0.7-0.8	26
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
0.7399	Intermediate Similarity	NPD6502	Phase 2
0.7288	Intermediate Similarity	NPD7773	Phase 2
0.7257	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3490	Discontinued
0.7091	Intermediate Similarity	NPD7477	Discontinued
0.7066	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6667	Approved
0.6994	Remote Similarity	NPD6666	Approved
0.6966	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6072	Discontinued
0.6952	Remote Similarity	NPD5557	Phase 1
0.6927	Remote Similarity	NPD1898	Discontinued
0.691	Remote Similarity	NPD4678	Approved
0.691	Remote Similarity	NPD4675	Approved
0.6905	Remote Similarity	NPD5124	Phase 1
0.6905	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6746	Phase 2
0.6882	Remote Similarity	NPD5605	Phase 2
0.6879	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6971	Discontinued
0.686	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7212	Phase 2
0.6857	Remote Similarity	NPD7213	Phase 3
0.6845	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3909	Discontinued
0.6818	Remote Similarity	NPD7447	Phase 1
0.6798	Remote Similarity	NPD4003	Phase 3
0.6782	Remote Similarity	NPD3750	Approved
0.6765	Remote Similarity	NPD7585	Approved
0.676	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD2415	Discontinued
0.675	Remote Similarity	NPD1548	Phase 1
0.6727	Remote Similarity	NPD3567	Approved
0.6727	Remote Similarity	NPD2797	Approved
0.6727	Remote Similarity	NPD3568	Approved
0.6726	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7583	Approved
0.6703	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5604	Discontinued
0.6684	Remote Similarity	NPD1729	Discontinued
0.6667	Remote Similarity	NPD4005	Discontinued
0.6667	Remote Similarity	NPD7549	Discontinued
0.6667	Remote Similarity	NPD5811	Approved
0.6667	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3823	Discontinued
0.6649	Remote Similarity	NPD5709	Phase 3
0.6649	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4433	Discontinued
0.6632	Remote Similarity	NPD3965	Phase 1
0.6631	Remote Similarity	NPD7608	Discontinued
0.6629	Remote Similarity	NPD3536	Discontinued
0.6629	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4123	Phase 3
0.6629	Remote Similarity	NPD2459	Approved
0.6629	Remote Similarity	NPD1652	Phase 2
0.6629	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD2458	Approved
0.6629	Remote Similarity	NPD2460	Phase 3
0.6628	Remote Similarity	NPD3554	Approved
0.6628	Remote Similarity	NPD3555	Approved
0.6628	Remote Similarity	NPD3553	Approved
0.6628	Remote Similarity	NPD3552	Approved
0.6627	Remote Similarity	NPD1296	Phase 2
0.6627	Remote Similarity	NPD1232	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD4666	Phase 3
0.6607	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4908	Phase 1
0.6606	Remote Similarity	NPD4129	Approved
0.6598	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7411	Suspended
0.6593	Remote Similarity	NPD2366	Approved
0.6591	Remote Similarity	NPD6331	Phase 2
0.659	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1610	Phase 2
0.6573	Remote Similarity	NPD4357	Discontinued
0.6571	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3052	Approved
0.657	Remote Similarity	NPD3054	Approved
0.6568	Remote Similarity	NPD4625	Phase 3
0.6568	Remote Similarity	NPD5163	Phase 2
0.6566	Remote Similarity	NPD3225	Approved
0.6561	Remote Similarity	NPD3951	Phase 3
0.6561	Remote Similarity	NPD3953	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3952	Approved
0.6561	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6894	Phase 1
0.6553	Remote Similarity	NPD7584	Approved
0.6552	Remote Similarity	NPD6604	Discontinued
0.6543	Remote Similarity	NPD6747	Phase 1
0.6541	Remote Similarity	NPD7768	Phase 2
0.6536	Remote Similarity	NPD7020	Approved
0.6536	Remote Similarity	NPD2874	Phase 2
0.6536	Remote Similarity	NPD7019	Approved
0.6535	Remote Similarity	NPD6874	Approved
0.6534	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD696	Discontinued
0.6529	Remote Similarity	NPD3268	Approved
0.6529	Remote Similarity	NPD1048	Approved
0.6528	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4377	Discontinued
0.6519	Remote Similarity	NPD5267	Discontinued
0.6514	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD654	Phase 3
0.6509	Remote Similarity	NPD2614	Approved
0.6506	Remote Similarity	NPD1669	Approved
0.6505	Remote Similarity	NPD3453	Discontinued
0.6505	Remote Similarity	NPD4055	Discovery
0.6505	Remote Similarity	NPD7075	Discontinued
0.6503	Remote Similarity	NPD5089	Approved
0.6503	Remote Similarity	NPD5090	Approved
0.6503	Remote Similarity	NPD7438	Suspended
0.65	Remote Similarity	NPD6312	Discontinued
0.6497	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6380	Phase 1
0.6494	Remote Similarity	NPD3748	Approved
0.6486	Remote Similarity	NPD7318	Phase 3
0.6486	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7153	Discontinued
0.6474	Remote Similarity	NPD2157	Approved
0.6474	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6801	Discontinued
0.6457	Remote Similarity	NPD4477	Approved
0.6457	Remote Similarity	NPD4476	Approved
0.6453	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.645	Remote Similarity	NPD4993	Discontinued
0.6444	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD2335	Discontinued
0.6443	Remote Similarity	NPD6104	Discontinued
0.6441	Remote Similarity	NPD6364	Approved
0.6441	Remote Similarity	NPD44	Approved
0.6437	Remote Similarity	NPD2200	Suspended
0.6432	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7819	Suspended
0.6432	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD8070	Approved
0.6414	Remote Similarity	NPD6841	Approved
0.6414	Remote Similarity	NPD6843	Phase 3
0.6414	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6842	Approved
0.6413	Remote Similarity	NPD3778	Approved
0.6413	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD2186	Approved
0.6407	Remote Similarity	NPD6582	Phase 2
0.6407	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD6583	Phase 3
0.6404	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD5623	Approved
0.6395	Remote Similarity	NPD2674	Phase 3
0.6392	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6184	Discontinued
0.6391	Remote Similarity	NPD3691	Phase 2
0.6391	Remote Similarity	NPD3690	Phase 2
0.6386	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD1549	Phase 2
0.6382	Remote Similarity	NPD7861	Discontinued
0.6379	Remote Similarity	NPD4097	Suspended
0.6378	Remote Similarity	NPD7317	Phase 3
0.6378	Remote Similarity	NPD5720	Discontinued
0.6375	Remote Similarity	NPD5535	Approved
0.6374	Remote Similarity	NPD3873	Phase 3
0.6374	Remote Similarity	NPD3869	Phase 3
0.6374	Remote Similarity	NPD1914	Approved
0.6374	Remote Similarity	NPD3136	Phase 2
0.6374	Remote Similarity	NPD7427	Discontinued
0.6374	Remote Similarity	NPD7131	Phase 3
0.6369	Remote Similarity	NPD302	Approved
0.6368	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD4466	Phase 1
0.6364	Remote Similarity	NPD2796	Approved
0.6364	Remote Similarity	NPD1538	Phase 1
0.6364	Remote Similarity	NPD1537	Approved
0.6364	Remote Similarity	NPD1519	Approved
0.6359	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3386	Phase 2
0.6358	Remote Similarity	NPD1240	Approved
0.6354	Remote Similarity	NPD3489	Phase 3
0.6354	Remote Similarity	NPD4443	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD3251	Approved
0.6349	Remote Similarity	NPD5677	Discontinued
0.6348	Remote Similarity	NPD1243	Approved
0.6348	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD8053	Approved
0.6345	Remote Similarity	NPD8054	Approved
0.6337	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5242	Approved
0.6335	Remote Similarity	NPD2388	Discontinued
0.633	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD6809	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