NPASS Compound

Structure

CID164269 OpenBabel06191715532D 31 33 0 0 1 0 0 0 0 0999 V2000 0.0000 6.0000 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 5.0000 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 -1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 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 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 2.5981 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 3.5000 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 -0.0000 2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 2.0000 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 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 16 18 2 0 0 0 0 16 31 1 0 0 0 0 17 25 2 0 0 0 0 17 28 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 24 1 0 0 0 0 21 30 1 0 0 0 0 22 26 2 0 0 0 0 22 29 1 0 0 0 0 23 27 2 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.17
Volume:	435.794
LogP:	3.701
LogD:	3.389
LogS:	-3.651
# Rotatable Bonds:	6
TPSA:	92.04
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	3.932
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.772
MDCK Permeability:	1.7674081391305663e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.152
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	83.83914947509766%
Volume Distribution (VD):	2.26
Pgp-substrate:	7.025940895080566%

ADMET: Metabolism

CYP1A2-inhibitor:	0.178
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.903
CYP2C19-substrate:	0.326
CYP2C9-inhibitor:	0.891
CYP2C9-substrate:	0.242
CYP2D6-inhibitor:	0.883
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.927
CYP3A4-substrate:	0.58

ADMET: Excretion

Clearance (CL):	4.968
Half-life (T1/2):	0.566

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.106
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.484
Skin Sensitization:	0.138
Carcinogencity:	0.795
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.135

Download Data

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

Natural Product: NPC164269

Natural Product ID:	NPC164269
*Common Name:**	Praeruptorin B
IUPAC Name:	[8,8-dimethyl-9-[(E)-2-methylbut-2-enoyl]oxy-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	PNTWXEIQXBRCPS-FNCQTZNRSA-N
Standard InCHI:	InChI=1S/C24H26O7/c1-7-13(3)22(26)29-20-18-16(11-9-15-10-12-17(25)28-19(15)18)31-24(5,6)21(20)30-23(27)14(4)8-2/h7-12,20-21H,1-6H3/b13-7+,14-8+
SMILES:	C/C=C(/C(=O)OC1c2c(ccc3c2oc(=O)cc3)OC(C1OC(=O)/C(=C/C)/C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3596578
PubChem CID:	5319259
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

*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
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[22784551]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[25068578]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30713	Angelica talwaniana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	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
IC50	1
MIC	4
Others	4

Activity Type	# Activity
Individual Protein	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2794	Individual Protein	Quinolone resistance protein norA	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[485122]
NPT2794	Individual Protein	Quinolone resistance protein norA	Staphylococcus aureus	FC	=	2.0	n.a.	PMID[485122]
NPT2795	Individual Protein	Fluoroquinolone resistance protein	Staphylococcus aureus	MIC	=	256.0	ug.mL-1	PMID[485122]
NPT2795	Individual Protein	Fluoroquinolone resistance protein	Staphylococcus aureus	FC	=	0.0	n.a.	PMID[485122]
NPT2	Others	Unspecified		MIC	=	32.0	ug.mL-1	PMID[485122]
NPT2	Others	Unspecified		FC	=	0.0	n.a.	PMID[485122]
NPT2	Others	Unspecified		MIC	=	64.0	ug.mL-1	PMID[485122]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	IC50	=	16000.0	nM	PMID[485122]

☑ 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 NPC164269 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	416
0.1-0.2	1699
0.2-0.3	4257
0.3-0.4	9547
0.4-0.5	8881
0.5-0.6	4023
0.6-0.7	5952
0.7-0.8	5353
0.8-0.85	1900
0.85-0.9	463
0.9-0.95	148
0.95-1	58

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC166672
1.0	High Similarity	NPC198381
1.0	High Similarity	NPC319859
1.0	High Similarity	NPC260265
1.0	High Similarity	NPC47163
1.0	High Similarity	NPC74655
1.0	High Similarity	NPC267412
1.0	High Similarity	NPC195343
1.0	High Similarity	NPC84894
1.0	High Similarity	NPC287182
1.0	High Similarity	NPC127888
1.0	High Similarity	NPC18804
1.0	High Similarity	NPC100986
0.9922	High Similarity	NPC86892
0.9922	High Similarity	NPC471909
0.9922	High Similarity	NPC472424
0.9922	High Similarity	NPC471625
0.9922	High Similarity	NPC281241
0.9921	High Similarity	NPC133956
0.9921	High Similarity	NPC167111
0.9921	High Similarity	NPC207002
0.9921	High Similarity	NPC318400
0.9921	High Similarity	NPC296624
0.9921	High Similarity	NPC471910
0.9845	High Similarity	NPC160727
0.9845	High Similarity	NPC128529
0.9845	High Similarity	NPC177281
0.9845	High Similarity	NPC283019
0.9845	High Similarity	NPC471630
0.9845	High Similarity	NPC149320
0.9845	High Similarity	NPC476455
0.9845	High Similarity	NPC55615
0.9695	High Similarity	NPC211110
0.969	High Similarity	NPC55149
0.969	High Similarity	NPC307412
0.9621	High Similarity	NPC312881
0.9612	High Similarity	NPC7526
0.9612	High Similarity	NPC222036
0.9549	High Similarity	NPC195357
0.9549	High Similarity	NPC287286
0.9549	High Similarity	NPC152771
0.9545	High Similarity	NPC279573
0.9535	High Similarity	NPC14248
0.947	High Similarity	NPC153818
0.947	High Similarity	NPC232246
0.947	High Similarity	NPC155963
0.9466	High Similarity	NPC469675
0.9407	High Similarity	NPC119640
0.9407	High Similarity	NPC183646
0.9398	High Similarity	NPC151946
0.9394	High Similarity	NPC283331
0.9394	High Similarity	NPC78746
0.9394	High Similarity	NPC224543
0.9394	High Similarity	NPC188380
0.938	High Similarity	NPC80170
0.937	High Similarity	NPC471826
0.9338	High Similarity	NPC476457
0.9323	High Similarity	NPC294456
0.9323	High Similarity	NPC212124
0.9323	High Similarity	NPC225106
0.9323	High Similarity	NPC281014
0.9323	High Similarity	NPC184861
0.9318	High Similarity	NPC472525
0.9302	High Similarity	NPC168710
0.9248	High Similarity	NPC26954
0.9248	High Similarity	NPC38099
0.9242	High Similarity	NPC62366
0.9242	High Similarity	NPC224475
0.9242	High Similarity	NPC213173
0.9242	High Similarity	NPC180716
0.9225	High Similarity	NPC472519
0.9225	High Similarity	NPC199204
0.9213	High Similarity	NPC73413
0.9213	High Similarity	NPC201667
0.9213	High Similarity	NPC111347
0.9173	High Similarity	NPC33986
0.9167	High Similarity	NPC31849
0.9141	High Similarity	NPC471828
0.9141	High Similarity	NPC471827
0.9134	High Similarity	NPC472518
0.9134	High Similarity	NPC109675
0.9134	High Similarity	NPC273772
0.913	High Similarity	NPC469701
0.913	High Similarity	NPC85624
0.9111	High Similarity	NPC270256
0.9098	High Similarity	NPC50896
0.9098	High Similarity	NPC98179
0.9098	High Similarity	NPC253574
0.9098	High Similarity	NPC326600
0.9098	High Similarity	NPC204353
0.9077	High Similarity	NPC185066
0.9077	High Similarity	NPC293642
0.9077	High Similarity	NPC139595
0.9077	High Similarity	NPC60704
0.907	High Similarity	NPC234109
0.907	High Similarity	NPC188327
0.9062	High Similarity	NPC27671
0.9062	High Similarity	NPC291899
0.9058	High Similarity	NPC471824
0.9055	High Similarity	NPC96286
0.9055	High Similarity	NPC248429
0.9023	High Similarity	NPC469955
0.9023	High Similarity	NPC469952
0.9015	High Similarity	NPC29734
0.9	High Similarity	NPC296377
0.9	High Similarity	NPC471764
0.9	High Similarity	NPC87950
0.8984	High Similarity	NPC290605
0.8984	High Similarity	NPC50720
0.8984	High Similarity	NPC154176
0.8984	High Similarity	NPC173350
0.8947	High Similarity	NPC194277
0.8947	High Similarity	NPC469956
0.8947	High Similarity	NPC19157
0.8939	High Similarity	NPC113098
0.8936	High Similarity	NPC169510
0.8931	High Similarity	NPC157212
0.8929	High Similarity	NPC171656
0.8906	High Similarity	NPC150214
0.8906	High Similarity	NPC13007
0.8906	High Similarity	NPC257188
0.8898	High Similarity	NPC180006
0.8898	High Similarity	NPC235190
0.8898	High Similarity	NPC163200
0.8897	High Similarity	NPC471068
0.8897	High Similarity	NPC471069
0.8881	High Similarity	NPC163557
0.8881	High Similarity	NPC469449
0.8872	High Similarity	NPC267336
0.8872	High Similarity	NPC272650
0.8855	High Similarity	NPC289316
0.8837	High Similarity	NPC315807
0.8832	High Similarity	NPC471072
0.8832	High Similarity	NPC471070
0.8832	High Similarity	NPC471071
0.8828	High Similarity	NPC144418
0.8824	High Similarity	NPC167517
0.8815	High Similarity	NPC309953
0.8815	High Similarity	NPC131950
0.8811	High Similarity	NPC103116
0.8806	High Similarity	NPC123954
0.8797	High Similarity	NPC19242
0.8794	High Similarity	NPC294365
0.8779	High Similarity	NPC163248
0.8759	High Similarity	NPC14697
0.8759	High Similarity	NPC306365
0.875	High Similarity	NPC311430
0.875	High Similarity	NPC224941
0.8741	High Similarity	NPC1220
0.8741	High Similarity	NPC472522
0.8741	High Similarity	NPC55147
0.8741	High Similarity	NPC241341
0.8741	High Similarity	NPC205797
0.8741	High Similarity	NPC141822
0.8741	High Similarity	NPC291551
0.8741	High Similarity	NPC142563
0.8741	High Similarity	NPC233018
0.8741	High Similarity	NPC54503
0.8741	High Similarity	NPC241165
0.8741	High Similarity	NPC36437
0.8741	High Similarity	NPC469965
0.874	High Similarity	NPC281356
0.874	High Similarity	NPC298796
0.8723	High Similarity	NPC76657
0.8723	High Similarity	NPC295696
0.8712	High Similarity	NPC243688
0.8712	High Similarity	NPC121740
0.8712	High Similarity	NPC258567
0.8712	High Similarity	NPC224774
0.8705	High Similarity	NPC472523
0.8702	High Similarity	NPC232692
0.8702	High Similarity	NPC202594
0.8696	High Similarity	NPC278600
0.8696	High Similarity	NPC144512
0.8696	High Similarity	NPC137262
0.8696	High Similarity	NPC35501
0.8696	High Similarity	NPC307883
0.8696	High Similarity	NPC37428
0.8696	High Similarity	NPC47040
0.8692	High Similarity	NPC143725
0.8686	High Similarity	NPC104796
0.8686	High Similarity	NPC286843
0.8681	High Similarity	NPC164299
0.8676	High Similarity	NPC147030
0.8667	High Similarity	NPC319969
0.8667	High Similarity	NPC175159
0.8667	High Similarity	NPC137669
0.8661	High Similarity	NPC96705
0.8661	High Similarity	NPC152306
0.8661	High Similarity	NPC265547
0.8657	High Similarity	NPC32463
0.8652	High Similarity	NPC471763
0.8647	High Similarity	NPC469453
0.8636	High Similarity	NPC101894
0.8623	High Similarity	NPC131198
0.8621	High Similarity	NPC180351
0.8613	High Similarity	NPC229128
0.8613	High Similarity	NPC234865
0.8593	High Similarity	NPC472517
0.8592	High Similarity	NPC43716

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 NPC164269 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	961
0.2-0.3	1775
0.3-0.4	2636
0.4-0.5	1874
0.5-0.6	1031
0.6-0.7	357
0.7-0.8	114
0.8-0.85	34
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8741	High Similarity	NPD5123	Clinical (unspecified phase)
0.8741	High Similarity	NPD5124	Phase 1
0.844	Intermediate Similarity	NPD1652	Phase 2
0.8258	Intermediate Similarity	NPD422	Phase 1
0.82	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD2796	Approved
0.8039	Intermediate Similarity	NPD7075	Discontinued
0.8028	Intermediate Similarity	NPD3748	Approved
0.8013	Intermediate Similarity	NPD6801	Discontinued
0.7987	Intermediate Similarity	NPD1653	Approved
0.7986	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1296	Phase 2
0.7986	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD920	Approved
0.7881	Intermediate Similarity	NPD4380	Phase 2
0.7877	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2424	Discontinued
0.7843	Intermediate Similarity	NPD7819	Suspended
0.7842	Intermediate Similarity	NPD4908	Phase 1
0.7838	Intermediate Similarity	NPD6799	Approved
0.7829	Intermediate Similarity	NPD7411	Suspended
0.7812	Intermediate Similarity	NPD5844	Phase 1
0.7808	Intermediate Similarity	NPD1243	Approved
0.7795	Intermediate Similarity	NPD1358	Approved
0.7785	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD5535	Approved
0.7761	Intermediate Similarity	NPD5691	Approved
0.7755	Intermediate Similarity	NPD3750	Approved
0.7746	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1613	Approved
0.7742	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1610	Phase 2
0.7712	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD7097	Phase 1
0.7707	Intermediate Similarity	NPD5494	Approved
0.7697	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1548	Phase 1
0.7687	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD5403	Approved
0.7677	Intermediate Similarity	NPD3817	Phase 2
0.7667	Intermediate Similarity	NPD5401	Approved
0.7647	Intermediate Similarity	NPD6599	Discontinued
0.7643	Intermediate Similarity	NPD919	Approved
0.7638	Intermediate Similarity	NPD9697	Approved
0.7628	Intermediate Similarity	NPD7768	Phase 2
0.7626	Intermediate Similarity	NPD2797	Approved
0.7626	Intermediate Similarity	NPD3266	Approved
0.7626	Intermediate Similarity	NPD3267	Approved
0.7622	Intermediate Similarity	NPD4307	Phase 2
0.7619	Intermediate Similarity	NPD1549	Phase 2
0.7606	Intermediate Similarity	NPD6798	Discontinued
0.7589	Intermediate Similarity	NPD6832	Phase 2
0.7589	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD3134	Approved
0.7564	Intermediate Similarity	NPD5402	Approved
0.7554	Intermediate Similarity	NPD3225	Approved
0.7554	Intermediate Similarity	NPD8651	Approved
0.7551	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1934	Approved
0.7535	Intermediate Similarity	NPD4625	Phase 3
0.7534	Intermediate Similarity	NPD7033	Discontinued
0.7518	Intermediate Similarity	NPD3496	Discontinued
0.7518	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD4060	Phase 1
0.7485	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3268	Approved
0.7482	Intermediate Similarity	NPD4749	Approved
0.7464	Intermediate Similarity	NPD1091	Approved
0.7455	Intermediate Similarity	NPD6559	Discontinued
0.7452	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4340	Discontinued
0.7448	Intermediate Similarity	NPD6355	Discontinued
0.7445	Intermediate Similarity	NPD4626	Approved
0.7431	Intermediate Similarity	NPD6233	Phase 2
0.7415	Intermediate Similarity	NPD1510	Phase 2
0.7415	Intermediate Similarity	NPD4308	Phase 3
0.7413	Intermediate Similarity	NPD3027	Phase 3
0.741	Intermediate Similarity	NPD7549	Discontinued
0.7407	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8455	Phase 2
0.7365	Intermediate Similarity	NPD1551	Phase 2
0.7365	Intermediate Similarity	NPD2935	Discontinued
0.7361	Intermediate Similarity	NPD2313	Discontinued
0.7347	Intermediate Similarity	NPD4536	Approved
0.7347	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4538	Approved
0.7342	Intermediate Similarity	NPD2415	Discontinued
0.7338	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1611	Approved
0.7333	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1933	Approved
0.7328	Intermediate Similarity	NPD2684	Approved
0.7324	Intermediate Similarity	NPD1019	Discontinued
0.7315	Intermediate Similarity	NPD6002	Phase 3
0.7315	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6004	Phase 3
0.7315	Intermediate Similarity	NPD6005	Phase 3
0.7315	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1241	Discontinued
0.7303	Intermediate Similarity	NPD5058	Phase 3
0.7297	Intermediate Similarity	NPD2799	Discontinued
0.7292	Intermediate Similarity	NPD7095	Approved
0.7285	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2801	Approved
0.7273	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2861	Phase 2
0.7267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3749	Approved
0.7239	Intermediate Similarity	NPD7843	Approved
0.7222	Intermediate Similarity	NPD1247	Approved
0.7215	Intermediate Similarity	NPD37	Approved
0.7214	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3818	Discontinued
0.7208	Intermediate Similarity	NPD2532	Approved
0.7208	Intermediate Similarity	NPD2533	Approved
0.7208	Intermediate Similarity	NPD2534	Approved
0.7206	Intermediate Similarity	NPD7157	Approved
0.72	Intermediate Similarity	NPD5763	Approved
0.72	Intermediate Similarity	NPD5762	Approved
0.7195	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6166	Phase 2
0.7195	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1778	Approved
0.719	Intermediate Similarity	NPD6667	Approved
0.719	Intermediate Similarity	NPD6666	Approved
0.7188	Intermediate Similarity	NPD4966	Approved
0.7188	Intermediate Similarity	NPD4967	Phase 2
0.7188	Intermediate Similarity	NPD4965	Approved
0.7186	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5588	Approved
0.7181	Intermediate Similarity	NPD5960	Phase 3
0.7178	Intermediate Similarity	NPD7229	Phase 3
0.7178	Intermediate Similarity	NPD6232	Discontinued
0.7171	Intermediate Similarity	NPD7466	Approved
0.717	Intermediate Similarity	NPD1465	Phase 2
0.7169	Intermediate Similarity	NPD7054	Approved
0.7163	Intermediate Similarity	NPD9717	Approved
0.7153	Intermediate Similarity	NPD3018	Phase 2
0.7143	Intermediate Similarity	NPD7212	Phase 2
0.7143	Intermediate Similarity	NPD4140	Approved
0.7143	Intermediate Similarity	NPD7213	Phase 3
0.7143	Intermediate Similarity	NPD1240	Approved
0.7143	Intermediate Similarity	NPD1511	Approved
0.7134	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6032	Approved
0.7133	Intermediate Similarity	NPD2438	Suspended
0.7133	Intermediate Similarity	NPD6099	Approved
0.7133	Intermediate Similarity	NPD6100	Approved
0.7126	Intermediate Similarity	NPD7472	Approved
0.7126	Intermediate Similarity	NPD7074	Phase 3
0.7125	Intermediate Similarity	NPD4288	Approved
0.7125	Intermediate Similarity	NPD5353	Approved
0.7124	Intermediate Similarity	NPD3887	Approved
0.7123	Intermediate Similarity	NPD7985	Registered
0.7122	Intermediate Similarity	NPD5585	Approved
0.7121	Intermediate Similarity	NPD290	Approved
0.7117	Intermediate Similarity	NPD7199	Phase 2
0.7117	Intermediate Similarity	NPD6959	Discontinued
0.7117	Intermediate Similarity	NPD8127	Discontinued
0.7107	Intermediate Similarity	NPD4433	Discontinued
0.7101	Intermediate Similarity	NPD7644	Approved
0.7101	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5536	Phase 2
0.7099	Intermediate Similarity	NPD6234	Discontinued
0.7097	Intermediate Similarity	NPD7447	Phase 1
0.7097	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD447	Suspended
0.7091	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2346	Discontinued
0.7086	Intermediate Similarity	NPD7266	Discontinued
0.7083	Intermediate Similarity	NPD6797	Phase 2
0.7081	Intermediate Similarity	NPD3882	Suspended
0.708	Intermediate Similarity	NPD6671	Approved
0.7075	Intermediate Similarity	NPD4062	Phase 3
0.7071	Intermediate Similarity	NPD17	Approved
0.7051	Intermediate Similarity	NPD1512	Approved
0.7048	Intermediate Similarity	NPD7473	Discontinued
0.7047	Intermediate Similarity	NPD1607	Approved
0.7042	Intermediate Similarity	NPD2981	Phase 2
0.7041	Intermediate Similarity	NPD7251	Discontinued
0.7039	Intermediate Similarity	NPD2897	Discontinued
0.703	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2979	Phase 3
0.7025	Intermediate Similarity	NPD3226	Approved
0.702	Intermediate Similarity	NPD4477	Approved
0.702	Intermediate Similarity	NPD4476	Approved
0.7014	Intermediate Similarity	NPD1203	Approved
0.7007	Intermediate Similarity	NPD1699	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