NPASS Compound

Structure

NPC476399 OpenBabel07101718292D 31 32 0 0 1 0 0 0 0 0999 V2000 -3.4641 1.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 -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 -1.7321 1.0000 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 5.1962 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 3.4641 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 3 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 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 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 3 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 4.3301 2.5000 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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 29 1 0 0 0 0 8 9 1 0 0 0 0 9 17 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 15 30 1 0 0 0 0 16 25 2 0 0 0 0 16 31 1 0 0 0 0 17 23 2 0 0 0 0 18 22 1 0 0 0 0 19 21 2 0 0 0 0 19 26 1 0 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 22 31 1 0 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.2
Volume:	446.987
LogP:	3.497
LogD:	3.41
LogS:	-5.0
# Rotatable Bonds:	12
TPSA:	72.45
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.383
Synthetic Accessibility Score:	3.352
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.569
MDCK Permeability:	2.9838745831511915e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.073

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	91.01184844970703%
Volume Distribution (VD):	0.785
Pgp-substrate:	10.411791801452637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.833
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.856
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.392
CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.949
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	4.924
Half-life (T1/2):	0.461

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.749
AMES Toxicity:	0.11
Rat Oral Acute Toxicity:	0.163
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.131
Carcinogencity:	0.389
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC476399

Natural Product ID:	NPC476399
*Common Name:**	[1-(3,4-Dimethoxyphenyl)-2-(2,6-Dimethoxy-3-Prop-2-Enylphenoxy)Propyl] Acetate
IUPAC Name:	[1-(3,4-dimethoxyphenyl)-2-(2,6-dimethoxy-3-prop-2-enylphenoxy)propyl] acetate
Synonyms:
Standard InCHIKey:	UUAVCSCWNKVAGM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H30O7/c1-8-9-17-10-13-20(27-5)24(23(17)29-7)30-15(2)22(31-16(3)25)18-11-12-19(26-4)21(14-18)28-6/h8,10-15,22H,1,9H2,2-7H3
SMILES:	C=CCc1ccc(c(c1OC)OC(C(c1ccc(c(c1)OC)OC)OC(=O)C)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL595416
PubChem CID:	46228397
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0001097] Benzyloxycarbonyls

*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
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11040054]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724856]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19900811]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8368081]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	Inhibition	=	27.2	%	PMID[568194]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	33200.0	nM	PMID[568194]

☑ 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 NPC476399 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	348
0.1-0.2	1548
0.2-0.3	4984
0.3-0.4	11974
0.4-0.5	5802
0.5-0.6	4149
0.6-0.7	7162
0.7-0.8	5580
0.8-0.85	880
0.85-0.9	245
0.9-0.95	16
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9837	High Similarity	NPC210674
0.968	High Similarity	NPC307042
0.968	High Similarity	NPC79184
0.9609	High Similarity	NPC311430
0.9609	High Similarity	NPC224941
0.952	High Similarity	NPC474623
0.952	High Similarity	NPC474651
0.9431	High Similarity	NPC279379
0.938	High Similarity	NPC474600
0.938	High Similarity	NPC309744
0.9365	High Similarity	NPC31707
0.935	High Similarity	NPC261661
0.9237	High Similarity	NPC286843
0.9237	High Similarity	NPC471719
0.9225	High Similarity	NPC319969
0.9219	High Similarity	NPC19242
0.9187	High Similarity	NPC472596
0.916	High Similarity	NPC234865
0.9154	High Similarity	NPC241341
0.9154	High Similarity	NPC36437
0.9154	High Similarity	NPC233018
0.9134	High Similarity	NPC474670
0.9134	High Similarity	NPC194841
0.9077	High Similarity	NPC137669
0.9032	High Similarity	NPC267064
0.9023	High Similarity	NPC865
0.9008	High Similarity	NPC263064
0.8992	High Similarity	NPC3439
0.8992	High Similarity	NPC190629
0.8992	High Similarity	NPC285339
0.8992	High Similarity	NPC202582
0.8992	High Similarity	NPC218856
0.8992	High Similarity	NPC470258
0.8992	High Similarity	NPC222004
0.8992	High Similarity	NPC210623
0.8992	High Similarity	NPC226788
0.8992	High Similarity	NPC273295
0.8984	High Similarity	NPC474119
0.8984	High Similarity	NPC242032
0.8984	High Similarity	NPC474821
0.8939	High Similarity	NPC309953
0.8939	High Similarity	NPC474478
0.8931	High Similarity	NPC5423
0.8923	High Similarity	NPC240722
0.8923	High Similarity	NPC244799
0.8915	High Similarity	NPC474616
0.8906	High Similarity	NPC285725
0.8906	High Similarity	NPC127604
0.8906	High Similarity	NPC474632
0.8906	High Similarity	NPC50683
0.8906	High Similarity	NPC112571
0.8906	High Similarity	NPC244364
0.8889	High Similarity	NPC288238
0.8872	High Similarity	NPC472337
0.8872	High Similarity	NPC470356
0.8872	High Similarity	NPC121812
0.8872	High Similarity	NPC61946
0.8872	High Similarity	NPC112246
0.8872	High Similarity	NPC94750
0.8872	High Similarity	NPC112939
0.8872	High Similarity	NPC474206
0.8871	High Similarity	NPC254625
0.8871	High Similarity	NPC475961
0.8864	High Similarity	NPC475840
0.8864	High Similarity	NPC168059
0.8864	High Similarity	NPC229442
0.8855	High Similarity	NPC472597
0.8855	High Similarity	NPC469613
0.8855	High Similarity	NPC469625
0.8855	High Similarity	NPC30043
0.8849	High Similarity	NPC476347
0.8849	High Similarity	NPC15577
0.8846	High Similarity	NPC474227
0.8846	High Similarity	NPC27239
0.8846	High Similarity	NPC123127
0.8824	High Similarity	NPC300611
0.8815	High Similarity	NPC43500
0.8815	High Similarity	NPC164148
0.8806	High Similarity	NPC306441
0.8806	High Similarity	NPC472336
0.8806	High Similarity	NPC78047
0.8806	High Similarity	NPC143895
0.8806	High Similarity	NPC227503
0.8806	High Similarity	NPC230734
0.8806	High Similarity	NPC16435
0.8806	High Similarity	NPC472334
0.8806	High Similarity	NPC474639
0.8788	High Similarity	NPC245120
0.8788	High Similarity	NPC35932
0.8788	High Similarity	NPC7903
0.8788	High Similarity	NPC160991
0.8788	High Similarity	NPC184447
0.8788	High Similarity	NPC16208
0.8786	High Similarity	NPC476348
0.8786	High Similarity	NPC93924
0.8786	High Similarity	NPC187398
0.878	High Similarity	NPC123948
0.8779	High Similarity	NPC474617
0.8779	High Similarity	NPC469614
0.8779	High Similarity	NPC472338
0.8779	High Similarity	NPC469612
0.8779	High Similarity	NPC470624
0.8779	High Similarity	NPC237169
0.8769	High Similarity	NPC222127
0.8769	High Similarity	NPC474636
0.8769	High Similarity	NPC82862
0.876	High Similarity	NPC9891
0.876	High Similarity	NPC88297
0.876	High Similarity	NPC186845
0.8741	High Similarity	NPC474530
0.8741	High Similarity	NPC474282
0.8741	High Similarity	NPC474521
0.8741	High Similarity	NPC211549
0.8741	High Similarity	NPC107551
0.8741	High Similarity	NPC326797
0.8741	High Similarity	NPC102904
0.8741	High Similarity	NPC176051
0.8741	High Similarity	NPC474540
0.8741	High Similarity	NPC477938
0.8741	High Similarity	NPC103976
0.874	High Similarity	NPC194626
0.8731	High Similarity	NPC195022
0.8731	High Similarity	NPC151224
0.8731	High Similarity	NPC260898
0.8731	High Similarity	NPC47398
0.8731	High Similarity	NPC234333
0.8731	High Similarity	NPC211386
0.8723	High Similarity	NPC30688
0.8723	High Similarity	NPC176903
0.8722	High Similarity	NPC11060
0.8722	High Similarity	NPC472522
0.872	High Similarity	NPC308217
0.8714	High Similarity	NPC178129
0.8712	High Similarity	NPC141493
0.8712	High Similarity	NPC469698
0.8712	High Similarity	NPC184928
0.8712	High Similarity	NPC473412
0.8712	High Similarity	NPC474238
0.8702	High Similarity	NPC469963
0.8702	High Similarity	NPC469951
0.8696	High Similarity	NPC34245
0.8696	High Similarity	NPC91492
0.8696	High Similarity	NPC7439
0.8696	High Similarity	NPC256555
0.8696	High Similarity	NPC110067
0.8696	High Similarity	NPC218510
0.8696	High Similarity	NPC138212
0.8696	High Similarity	NPC76415
0.8692	High Similarity	NPC473092
0.8692	High Similarity	NPC98745
0.8692	High Similarity	NPC8050
0.8692	High Similarity	NPC210355
0.8692	High Similarity	NPC473093
0.8682	High Similarity	NPC105925
0.8676	High Similarity	NPC270256
0.8676	High Similarity	NPC471388
0.8672	High Similarity	NPC108545
0.8667	High Similarity	NPC248727
0.8667	High Similarity	NPC172818
0.8667	High Similarity	NPC302701
0.8667	High Similarity	NPC270456
0.8667	High Similarity	NPC173660
0.8667	High Similarity	NPC269091
0.8667	High Similarity	NPC265433
0.8667	High Similarity	NPC162659
0.8667	High Similarity	NPC25695
0.8667	High Similarity	NPC11453
0.8662	High Similarity	NPC21184
0.8662	High Similarity	NPC120426
0.8662	High Similarity	NPC205727
0.8662	High Similarity	NPC294522
0.8661	High Similarity	NPC477886
0.8657	High Similarity	NPC170694
0.8657	High Similarity	NPC317380
0.8657	High Similarity	NPC111635
0.8657	High Similarity	NPC310854
0.8652	High Similarity	NPC477879
0.8651	High Similarity	NPC471504
0.8651	High Similarity	NPC473290
0.8651	High Similarity	NPC222175
0.8647	High Similarity	NPC470752
0.8647	High Similarity	NPC127624
0.8647	High Similarity	NPC202762
0.8647	High Similarity	NPC475856
0.8647	High Similarity	NPC86655
0.8643	High Similarity	NPC268515
0.8643	High Similarity	NPC40222
0.8643	High Similarity	NPC475872
0.8643	High Similarity	NPC205361
0.8636	High Similarity	NPC91291
0.8636	High Similarity	NPC214860
0.8633	High Similarity	NPC87883
0.8633	High Similarity	NPC326144
0.8626	High Similarity	NPC281864
0.8626	High Similarity	NPC328682
0.8626	High Similarity	NPC54321
0.8623	High Similarity	NPC472562
0.8623	High Similarity	NPC174522
0.8623	High Similarity	NPC80326
0.8623	High Similarity	NPC131971

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 NPC476399 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	925
0.2-0.3	1909
0.3-0.4	2657
0.4-0.5	1617
0.5-0.6	966
0.6-0.7	593
0.7-0.8	178
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8561	High Similarity	NPD3027	Phase 3
0.8507	High Similarity	NPD1612	Clinical (unspecified phase)
0.8507	High Similarity	NPD1613	Approved
0.8409	Intermediate Similarity	NPD3018	Phase 2
0.8358	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.8308	Intermediate Similarity	NPD2981	Phase 2
0.8271	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8244	Intermediate Similarity	NPD2983	Phase 2
0.8244	Intermediate Similarity	NPD2982	Phase 2
0.8243	Intermediate Similarity	NPD3817	Phase 2
0.8095	Intermediate Similarity	NPD5283	Phase 1
0.8082	Intermediate Similarity	NPD1653	Approved
0.7987	Intermediate Similarity	NPD1934	Approved
0.7955	Intermediate Similarity	NPD3705	Approved
0.7955	Intermediate Similarity	NPD422	Phase 1
0.7947	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD4908	Phase 1
0.7923	Intermediate Similarity	NPD1548	Phase 1
0.7902	Intermediate Similarity	NPD1652	Phase 2
0.7874	Intermediate Similarity	NPD5535	Approved
0.7867	Intermediate Similarity	NPD37	Approved
0.7857	Intermediate Similarity	NPD7199	Phase 2
0.7846	Intermediate Similarity	NPD5536	Phase 2
0.7842	Intermediate Similarity	NPD4060	Phase 1
0.7829	Intermediate Similarity	NPD4966	Approved
0.7829	Intermediate Similarity	NPD4967	Phase 2
0.7829	Intermediate Similarity	NPD4965	Approved
0.7826	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1610	Phase 2
0.7817	Intermediate Similarity	NPD3539	Phase 1
0.7815	Intermediate Similarity	NPD2801	Approved
0.7815	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD6799	Approved
0.7793	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD5494	Approved
0.7785	Intermediate Similarity	NPD5844	Phase 1
0.777	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD3540	Phase 1
0.7756	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3496	Discontinued
0.7727	Intermediate Similarity	NPD6234	Discontinued
0.7727	Intermediate Similarity	NPD5585	Approved
0.7712	Intermediate Similarity	NPD3882	Suspended
0.7703	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD6798	Discontinued
0.7692	Intermediate Similarity	NPD2796	Approved
0.7681	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6355	Discontinued
0.766	Intermediate Similarity	NPD5124	Phase 1
0.766	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6233	Phase 2
0.7622	Intermediate Similarity	NPD3748	Approved
0.7619	Intermediate Similarity	NPD1358	Approved
0.7613	Intermediate Similarity	NPD919	Approved
0.7609	Intermediate Similarity	NPD2861	Phase 2
0.7603	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4110	Phase 3
0.7595	Intermediate Similarity	NPD6166	Phase 2
0.7595	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD5691	Approved
0.7582	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6032	Approved
0.7568	Intermediate Similarity	NPD1511	Approved
0.7562	Intermediate Similarity	NPD7054	Approved
0.7556	Intermediate Similarity	NPD1091	Approved
0.7556	Intermediate Similarity	NPD1611	Approved
0.7554	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD17	Approved
0.7537	Intermediate Similarity	NPD1778	Approved
0.7535	Intermediate Similarity	NPD1933	Approved
0.7532	Intermediate Similarity	NPD5402	Approved
0.7517	Intermediate Similarity	NPD5762	Approved
0.7517	Intermediate Similarity	NPD7266	Discontinued
0.7517	Intermediate Similarity	NPD5763	Approved
0.7516	Intermediate Similarity	NPD7074	Phase 3
0.7516	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD4678	Approved
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD4675	Approved
0.75	Intermediate Similarity	NPD7095	Approved
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7549	Discontinued
0.7483	Intermediate Similarity	NPD3686	Approved
0.7483	Intermediate Similarity	NPD3687	Approved
0.7468	Intermediate Similarity	NPD7819	Suspended
0.7468	Intermediate Similarity	NPD6232	Discontinued
0.7467	Intermediate Similarity	NPD1512	Approved
0.7452	Intermediate Similarity	NPD5677	Discontinued
0.7451	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1296	Phase 2
0.7445	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD4359	Approved
0.7445	Intermediate Similarity	NPD4749	Approved
0.7436	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7075	Discontinued
0.7434	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6832	Phase 2
0.7422	Intermediate Similarity	NPD2684	Approved
0.7421	Intermediate Similarity	NPD5242	Approved
0.7419	Intermediate Similarity	NPD5353	Approved
0.7419	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5403	Approved
0.7415	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6674	Discontinued
0.7413	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4340	Discontinued
0.7413	Intermediate Similarity	NPD447	Suspended
0.7403	Intermediate Similarity	NPD6801	Discontinued
0.7402	Intermediate Similarity	NPD3134	Approved
0.74	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5401	Approved
0.74	Intermediate Similarity	NPD3146	Approved
0.7394	Intermediate Similarity	NPD4062	Phase 3
0.7391	Intermediate Similarity	NPD7228	Approved
0.7385	Intermediate Similarity	NPD228	Approved
0.7383	Intermediate Similarity	NPD7124	Phase 2
0.7379	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7033	Discontinued
0.7378	Intermediate Similarity	NPD7808	Phase 3
0.7372	Intermediate Similarity	NPD1608	Approved
0.7365	Intermediate Similarity	NPD3750	Approved
0.7365	Intermediate Similarity	NPD4628	Phase 3
0.7362	Intermediate Similarity	NPD6797	Phase 2
0.7362	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2653	Approved
0.7355	Intermediate Similarity	NPD1465	Phase 2
0.7344	Intermediate Similarity	NPD290	Approved
0.7338	Intermediate Similarity	NPD6385	Approved
0.7338	Intermediate Similarity	NPD6386	Approved
0.7333	Intermediate Similarity	NPD4357	Discontinued
0.7329	Intermediate Similarity	NPD1551	Phase 2
0.7329	Intermediate Similarity	NPD7473	Discontinued
0.7329	Intermediate Similarity	NPD2438	Suspended
0.7328	Intermediate Similarity	NPD7843	Approved
0.7324	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7251	Discontinued
0.7312	Intermediate Similarity	NPD3926	Phase 2
0.731	Intermediate Similarity	NPD7097	Phase 1
0.7296	Intermediate Similarity	NPD1247	Approved
0.7293	Intermediate Similarity	NPD7157	Approved
0.7292	Intermediate Similarity	NPD230	Phase 1
0.7285	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4626	Approved
0.7279	Intermediate Similarity	NPD1375	Discontinued
0.7279	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4870	Approved
0.7273	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4972	Discontinued
0.7266	Intermediate Similarity	NPD2922	Phase 1
0.7266	Intermediate Similarity	NPD8651	Approved
0.7266	Intermediate Similarity	NPD3225	Approved
0.7259	Intermediate Similarity	NPD1894	Discontinued
0.725	Intermediate Similarity	NPD7229	Phase 3
0.7248	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6653	Approved
0.7237	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1549	Phase 2
0.723	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7411	Suspended
0.7222	Intermediate Similarity	NPD4140	Approved
0.7222	Intermediate Similarity	NPD2979	Phase 3
0.7222	Intermediate Similarity	NPD1558	Phase 1
0.7215	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3267	Approved
0.7214	Intermediate Similarity	NPD3266	Approved
0.7214	Intermediate Similarity	NPD2797	Approved
0.7212	Intermediate Similarity	NPD7240	Approved
0.7211	Intermediate Similarity	NPD2935	Discontinued
0.7206	Intermediate Similarity	NPD1357	Approved
0.72	Intermediate Similarity	NPD6190	Approved
0.72	Intermediate Similarity	NPD2219	Phase 1
0.72	Intermediate Similarity	NPD2677	Approved
0.7192	Intermediate Similarity	NPD4538	Approved
0.7192	Intermediate Similarity	NPD4536	Approved
0.7192	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6111	Discontinued
0.719	Intermediate Similarity	NPD920	Approved
0.7188	Intermediate Similarity	NPD9697	Approved
0.7188	Intermediate Similarity	NPD8127	Discontinued
0.7181	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4236	Phase 3
0.7181	Intermediate Similarity	NPD4237	Approved
0.7181	Intermediate Similarity	NPD4162	Approved
0.7171	Intermediate Similarity	NPD4123	Phase 3
0.7164	Intermediate Similarity	NPD6671	Approved
0.7163	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4380	Phase 2
0.716	Intermediate Similarity	NPD4481	Phase 3
0.7152	Intermediate Similarity	NPD7768	Phase 2
0.7143	Intermediate Similarity	NPD4210	Discontinued

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