NPASS Compound

Structure

NPC184065 OpenBabel07101718282D 27 29 0 0 1 0 0 0 0 0999 V2000 -3.6950 -0.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4469 -1.9943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0224 1.7708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0224 1.7708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6901 0.7237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0447 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0447 0.6032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5224 -0.3016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1358 0.3335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4718 -0.6722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3261 1.1106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7531 0.2873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5185 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9277 -0.2772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4718 1.2753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8748 1.3612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8748 -0.7580 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.6032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4714 1.2468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3261 -0.5074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5224 0.9048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3762 -3.3558 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7325 2.3510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0821 2.0387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3288 -1.2632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7325 -1.7478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 15 2 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 23 2 0 0 0 0 13 27 1 0 0 0 0 14 9 1 1 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 24 1 6 0 0 0 17 20 1 0 0 0 0 17 27 1 1 0 0 0 18 21 1 0 0 0 0 18 22 1 6 0 0 0 19 25 2 0 0 0 0 20 22 1 0 0 0 0 20 26 2 0 0 0 0 22 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.21
Volume:	394.168
LogP:	2.759
LogD:	1.134
LogS:	-2.78
# Rotatable Bonds:	2
TPSA:	77.51
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.517
Synthetic Accessibility Score:	5.761
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.885
MDCK Permeability:	1.9523786249919794e-05
Pgp-inhibitor:	0.902
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.266
Plasma Protein Binding (PPB):	81.6236343383789%
Volume Distribution (VD):	0.654
Pgp-substrate:	30.100744247436523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.376
CYP2C19-inhibitor:	0.235
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.443
CYP2C9-substrate:	0.495
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.731
CYP3A4-substrate:	0.427

ADMET: Excretion

Clearance (CL):	4.944
Half-life (T1/2):	0.735

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.7
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.682
Maximum Recommended Daily Dose:	0.858
Skin Sensitization:	0.364
Carcinogencity:	0.242
Eye Corrosion:	0.872
Eye Irritation:	0.702
Respiratory Toxicity:	0.682

Download Data

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

Natural Product: NPC184065

Natural Product ID:	NPC184065
*Common Name:**	WJAMERXGFWVGIW-NVQRBQOGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WJAMERXGFWVGIW-NVQRBQOGSA-N
Standard InCHI:	InChI=1S/C22H30O5/c1-12-14-9-15(19(12)25)16(24)11-18-21(3,4)7-6-8-22(18,5)20(26)17(10-14)27-13(2)23/h9,14,16-18,24H,1,6-8,10-11H2,2-5H3/t14-,16+,17-,18+,22+/m0/s1
SMILES:	C=C1[C@H]2C=C([C@@H](C[C@@H]3C(C)(C)CCC[C@@]3(C)C(=O)[C@H](C2)OC(=O)C)O)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461699
PubChem CID:	3010861
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0003677] Alpha-acyloxy carbonyl compounds [CHEMONTID:0003420] Alpha-acyloxy ketones

*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
NPO9759	Croton kongensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828479]
NPO9759	Croton kongensis	Species	Euphorbiaceae	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	4
MIC	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	0.9	ug.mL-1	PMID[454381]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.2	ug.mL-1	PMID[454381]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.1	ug.mL-1	PMID[454381]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	6.25	ug.mL-1	PMID[454381]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	1.0	ug.mL-1	PMID[454381]

☑ 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 NPC184065 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	189
0.1-0.2	1156
0.2-0.3	4874
0.3-0.4	9314
0.4-0.5	13227
0.5-0.6	7017
0.6-0.7	5577
0.7-0.8	1309
0.8-0.85	30
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.913	High Similarity	NPC148463
0.9053	High Similarity	NPC306856
0.8404	Intermediate Similarity	NPC51486
0.837	Intermediate Similarity	NPC202394
0.8333	Intermediate Similarity	NPC53685
0.8316	Intermediate Similarity	NPC472814
0.8316	Intermediate Similarity	NPC177037
0.8265	Intermediate Similarity	NPC474343
0.8229	Intermediate Similarity	NPC115021
0.82	Intermediate Similarity	NPC472643
0.8182	Intermediate Similarity	NPC222011
0.8172	Intermediate Similarity	NPC194417
0.8163	Intermediate Similarity	NPC242848
0.8144	Intermediate Similarity	NPC469632
0.8125	Intermediate Similarity	NPC219874
0.8105	Intermediate Similarity	NPC5509
0.81	Intermediate Similarity	NPC117685
0.81	Intermediate Similarity	NPC472644
0.81	Intermediate Similarity	NPC476274
0.81	Intermediate Similarity	NPC174314
0.8081	Intermediate Similarity	NPC69385
0.8081	Intermediate Similarity	NPC475709
0.8065	Intermediate Similarity	NPC261380
0.8061	Intermediate Similarity	NPC209355
0.8041	Intermediate Similarity	NPC109414
0.8037	Intermediate Similarity	NPC472926
0.8037	Intermediate Similarity	NPC472929
0.8021	Intermediate Similarity	NPC471818
0.802	Intermediate Similarity	NPC476223
0.802	Intermediate Similarity	NPC224720
0.802	Intermediate Similarity	NPC476240
0.802	Intermediate Similarity	NPC472924
0.8	Intermediate Similarity	NPC316598
0.8	Intermediate Similarity	NPC141191
0.8	Intermediate Similarity	NPC474854
0.7981	Intermediate Similarity	NPC472925
0.798	Intermediate Similarity	NPC185553
0.7979	Intermediate Similarity	NPC261721
0.7959	Intermediate Similarity	NPC476596
0.7921	Intermediate Similarity	NPC471041
0.7921	Intermediate Similarity	NPC477521
0.79	Intermediate Similarity	NPC169205
0.79	Intermediate Similarity	NPC53844
0.79	Intermediate Similarity	NPC208094
0.7895	Intermediate Similarity	NPC471738
0.7895	Intermediate Similarity	NPC312561
0.7885	Intermediate Similarity	NPC123726
0.7885	Intermediate Similarity	NPC1679
0.7885	Intermediate Similarity	NPC284365
0.7872	Intermediate Similarity	NPC65661
0.7872	Intermediate Similarity	NPC86316
0.7872	Intermediate Similarity	NPC106416
0.7872	Intermediate Similarity	NPC474853
0.7872	Intermediate Similarity	NPC179006
0.7864	Intermediate Similarity	NPC472755
0.7857	Intermediate Similarity	NPC476598
0.7857	Intermediate Similarity	NPC139692
0.7857	Intermediate Similarity	NPC476597
0.7857	Intermediate Similarity	NPC475302
0.7857	Intermediate Similarity	NPC476416
0.7843	Intermediate Similarity	NPC81530
0.7843	Intermediate Similarity	NPC475099
0.7835	Intermediate Similarity	NPC281942
0.7835	Intermediate Similarity	NPC232426
0.7835	Intermediate Similarity	NPC77337
0.7835	Intermediate Similarity	NPC230332
0.783	Intermediate Similarity	NPC475941
0.783	Intermediate Similarity	NPC474901
0.7822	Intermediate Similarity	NPC23364
0.7822	Intermediate Similarity	NPC197386
0.7822	Intermediate Similarity	NPC471717
0.7818	Intermediate Similarity	NPC472927
0.7812	Intermediate Similarity	NPC472870
0.7812	Intermediate Similarity	NPC104560
0.7812	Intermediate Similarity	NPC53454
0.781	Intermediate Similarity	NPC475294
0.78	Intermediate Similarity	NPC29152
0.78	Intermediate Similarity	NPC134072
0.78	Intermediate Similarity	NPC328371
0.78	Intermediate Similarity	NPC234993
0.78	Intermediate Similarity	NPC471039
0.7789	Intermediate Similarity	NPC198761
0.7778	Intermediate Similarity	NPC184870
0.7778	Intermediate Similarity	NPC121825
0.7778	Intermediate Similarity	NPC471040
0.7767	Intermediate Similarity	NPC118405
0.7767	Intermediate Similarity	NPC308726
0.7767	Intermediate Similarity	NPC119601
0.7767	Intermediate Similarity	NPC136289
0.7766	Intermediate Similarity	NPC149869
0.7766	Intermediate Similarity	NPC474359
0.7755	Intermediate Similarity	NPC261607
0.7755	Intermediate Similarity	NPC300312
0.7755	Intermediate Similarity	NPC172101
0.7755	Intermediate Similarity	NPC477783
0.7755	Intermediate Similarity	NPC111114
0.7755	Intermediate Similarity	NPC141831
0.7745	Intermediate Similarity	NPC472972
0.7745	Intermediate Similarity	NPC474012
0.7745	Intermediate Similarity	NPC476299
0.7745	Intermediate Similarity	NPC287833
0.7742	Intermediate Similarity	NPC85772
0.7736	Intermediate Similarity	NPC220155
0.7736	Intermediate Similarity	NPC476479
0.7732	Intermediate Similarity	NPC52198
0.7732	Intermediate Similarity	NPC123912
0.7732	Intermediate Similarity	NPC174342
0.7732	Intermediate Similarity	NPC117405
0.7723	Intermediate Similarity	NPC156546
0.7723	Intermediate Similarity	NPC253826
0.7717	Intermediate Similarity	NPC45495
0.7714	Intermediate Similarity	NPC472645
0.77	Intermediate Similarity	NPC470978
0.77	Intermediate Similarity	NPC295347
0.77	Intermediate Similarity	NPC48803
0.77	Intermediate Similarity	NPC474490
0.77	Intermediate Similarity	NPC174948
0.77	Intermediate Similarity	NPC470974
0.77	Intermediate Similarity	NPC173875
0.77	Intermediate Similarity	NPC193645
0.77	Intermediate Similarity	NPC318282
0.77	Intermediate Similarity	NPC90121
0.77	Intermediate Similarity	NPC476174
0.77	Intermediate Similarity	NPC275960
0.77	Intermediate Similarity	NPC134067
0.77	Intermediate Similarity	NPC469995
0.7692	Intermediate Similarity	NPC475994
0.7692	Intermediate Similarity	NPC95899
0.7692	Intermediate Similarity	NPC62336
0.7692	Intermediate Similarity	NPC72151
0.7692	Intermediate Similarity	NPC192006
0.7692	Intermediate Similarity	NPC131366
0.7692	Intermediate Similarity	NPC198240
0.7685	Intermediate Similarity	NPC472928
0.7684	Intermediate Similarity	NPC52628
0.7684	Intermediate Similarity	NPC189311
0.7684	Intermediate Similarity	NPC79573
0.7684	Intermediate Similarity	NPC125290
0.7679	Intermediate Similarity	NPC472933
0.7677	Intermediate Similarity	NPC271652
0.7677	Intermediate Similarity	NPC469692
0.7677	Intermediate Similarity	NPC469645
0.767	Intermediate Similarity	NPC471412
0.767	Intermediate Similarity	NPC46998
0.767	Intermediate Similarity	NPC282524
0.767	Intermediate Similarity	NPC163372
0.767	Intermediate Similarity	NPC185141
0.767	Intermediate Similarity	NPC128733
0.767	Intermediate Similarity	NPC472753
0.767	Intermediate Similarity	NPC110443
0.767	Intermediate Similarity	NPC302537
0.767	Intermediate Similarity	NPC133907
0.766	Intermediate Similarity	NPC222358
0.7658	Intermediate Similarity	NPC472934
0.7653	Intermediate Similarity	NPC477147
0.7653	Intermediate Similarity	NPC469368
0.7653	Intermediate Similarity	NPC232202
0.7653	Intermediate Similarity	NPC145666
0.7653	Intermediate Similarity	NPC477782
0.7653	Intermediate Similarity	NPC477149
0.7653	Intermediate Similarity	NPC472866
0.7647	Intermediate Similarity	NPC54843
0.7647	Intermediate Similarity	NPC478056
0.7642	Intermediate Similarity	NPC44063
0.7642	Intermediate Similarity	NPC91034
0.7634	Intermediate Similarity	NPC90055
0.7629	Intermediate Similarity	NPC471047
0.7629	Intermediate Similarity	NPC475906
0.7629	Intermediate Similarity	NPC476805
0.7629	Intermediate Similarity	NPC469653
0.7629	Intermediate Similarity	NPC469631
0.7629	Intermediate Similarity	NPC72397
0.7629	Intermediate Similarity	NPC469628
0.7624	Intermediate Similarity	NPC472941
0.7624	Intermediate Similarity	NPC456
0.7624	Intermediate Similarity	NPC202833
0.7624	Intermediate Similarity	NPC476797
0.7624	Intermediate Similarity	NPC250757
0.7624	Intermediate Similarity	NPC301534
0.7619	Intermediate Similarity	NPC13385
0.7619	Intermediate Similarity	NPC118911
0.7619	Intermediate Similarity	NPC235889
0.7615	Intermediate Similarity	NPC264634
0.7615	Intermediate Similarity	NPC475970
0.7609	Intermediate Similarity	NPC7232
0.7609	Intermediate Similarity	NPC308038
0.7604	Intermediate Similarity	NPC229717
0.7604	Intermediate Similarity	NPC475461
0.7604	Intermediate Similarity	NPC220478
0.7604	Intermediate Similarity	NPC472869
0.7604	Intermediate Similarity	NPC305475
0.7604	Intermediate Similarity	NPC322159
0.76	Intermediate Similarity	NPC90453
0.76	Intermediate Similarity	NPC476415
0.76	Intermediate Similarity	NPC167219
0.7596	Intermediate Similarity	NPC320447
0.7596	Intermediate Similarity	NPC472754
0.7593	Intermediate Similarity	NPC29133
0.7593	Intermediate Similarity	NPC153036
0.7593	Intermediate Similarity	NPC5103

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 NPC184065 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1611
0.2-0.3	3734
0.3-0.4	2354
0.4-0.5	805
0.5-0.6	260
0.6-0.7	174
0.7-0.8	45
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
0.77	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD5697	Approved
0.757	Intermediate Similarity	NPD6881	Approved
0.757	Intermediate Similarity	NPD6899	Approved
0.757	Intermediate Similarity	NPD6011	Approved
0.7553	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD6083	Phase 2
0.7549	Intermediate Similarity	NPD6084	Phase 2
0.7547	Intermediate Similarity	NPD5739	Approved
0.7547	Intermediate Similarity	NPD6675	Approved
0.7547	Intermediate Similarity	NPD6402	Approved
0.7547	Intermediate Similarity	NPD7128	Approved
0.7525	Intermediate Similarity	NPD5695	Phase 3
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD5701	Approved
0.7476	Intermediate Similarity	NPD4225	Approved
0.7475	Intermediate Similarity	NPD5785	Approved
0.7449	Intermediate Similarity	NPD5737	Approved
0.7449	Intermediate Similarity	NPD6672	Approved
0.7431	Intermediate Similarity	NPD6883	Approved
0.7431	Intermediate Similarity	NPD7290	Approved
0.7431	Intermediate Similarity	NPD7102	Approved
0.7407	Intermediate Similarity	NPD7320	Approved
0.7364	Intermediate Similarity	NPD6649	Approved
0.7364	Intermediate Similarity	NPD8130	Phase 1
0.7364	Intermediate Similarity	NPD6617	Approved
0.7364	Intermediate Similarity	NPD6650	Approved
0.7364	Intermediate Similarity	NPD6869	Approved
0.7364	Intermediate Similarity	NPD6847	Approved
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD6372	Approved
0.7327	Intermediate Similarity	NPD5779	Approved
0.7327	Intermediate Similarity	NPD5778	Approved
0.732	Intermediate Similarity	NPD5363	Approved
0.7308	Intermediate Similarity	NPD5696	Approved
0.7297	Intermediate Similarity	NPD6882	Approved
0.7297	Intermediate Similarity	NPD8297	Approved
0.7282	Intermediate Similarity	NPD5222	Approved
0.7282	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5221	Approved
0.7264	Intermediate Similarity	NPD5211	Phase 2
0.7245	Intermediate Similarity	NPD5279	Phase 3
0.7245	Intermediate Similarity	NPD5786	Approved
0.7228	Intermediate Similarity	NPD6411	Approved
0.7212	Intermediate Similarity	NPD5173	Approved
0.7207	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4695	Discontinued
0.7155	Intermediate Similarity	NPD6319	Approved
0.713	Intermediate Similarity	NPD5141	Approved
0.7128	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4697	Phase 3
0.7105	Intermediate Similarity	NPD6274	Approved
0.7105	Intermediate Similarity	NPD6868	Approved
0.7087	Intermediate Similarity	NPD5282	Discontinued
0.7087	Intermediate Similarity	NPD7748	Approved
0.7075	Intermediate Similarity	NPD7639	Approved
0.7075	Intermediate Similarity	NPD5286	Approved
0.7075	Intermediate Similarity	NPD4696	Approved
0.7075	Intermediate Similarity	NPD5285	Approved
0.7075	Intermediate Similarity	NPD7640	Approved
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD7521	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7059	Intermediate Similarity	NPD5693	Phase 1
0.7059	Intermediate Similarity	NPD6079	Approved
0.7059	Intermediate Similarity	NPD7515	Phase 2
0.7048	Intermediate Similarity	NPD4755	Approved
0.7043	Intermediate Similarity	NPD7115	Discovery
0.7043	Intermediate Similarity	NPD6317	Approved
0.7041	Intermediate Similarity	NPD3133	Approved
0.7041	Intermediate Similarity	NPD3666	Approved
0.7041	Intermediate Similarity	NPD3665	Phase 1
0.703	Intermediate Similarity	NPD6673	Approved
0.703	Intermediate Similarity	NPD6101	Approved
0.703	Intermediate Similarity	NPD6904	Approved
0.703	Intermediate Similarity	NPD4753	Phase 2
0.703	Intermediate Similarity	NPD6080	Approved
0.703	Intermediate Similarity	NPD5328	Approved
0.703	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4269	Approved
0.701	Intermediate Similarity	NPD5209	Approved
0.701	Intermediate Similarity	NPD4270	Approved
0.7009	Intermediate Similarity	NPD5223	Approved
0.699	Remote Similarity	NPD6399	Phase 3
0.6983	Remote Similarity	NPD6313	Approved
0.6983	Remote Similarity	NPD6314	Approved
0.6983	Remote Similarity	NPD6335	Approved
0.6981	Remote Similarity	NPD7638	Approved
0.697	Remote Similarity	NPD1694	Approved
0.697	Remote Similarity	NPD1696	Phase 3
0.6964	Remote Similarity	NPD6371	Approved
0.6961	Remote Similarity	NPD5692	Phase 3
0.6944	Remote Similarity	NPD5226	Approved
0.6944	Remote Similarity	NPD5225	Approved
0.6944	Remote Similarity	NPD4633	Approved
0.6944	Remote Similarity	NPD5224	Approved
0.6939	Remote Similarity	NPD5362	Discontinued
0.6939	Remote Similarity	NPD7154	Phase 3
0.6937	Remote Similarity	NPD6686	Approved
0.6931	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6903	Approved
0.693	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD7101	Approved
0.6923	Remote Similarity	NPD7100	Approved
0.6917	Remote Similarity	NPD7492	Approved
0.6916	Remote Similarity	NPD4700	Approved
0.69	Remote Similarity	NPD3618	Phase 1
0.69	Remote Similarity	NPD4519	Discontinued
0.69	Remote Similarity	NPD4623	Approved
0.6897	Remote Similarity	NPD6009	Approved
0.6893	Remote Similarity	NPD6050	Approved
0.6893	Remote Similarity	NPD7637	Suspended
0.6893	Remote Similarity	NPD5694	Approved
0.6887	Remote Similarity	NPD7902	Approved
0.6881	Remote Similarity	NPD5175	Approved
0.6881	Remote Similarity	NPD5174	Approved
0.6864	Remote Similarity	NPD6054	Approved
0.686	Remote Similarity	NPD6616	Approved
0.6857	Remote Similarity	NPD5210	Approved
0.6857	Remote Similarity	NPD4629	Approved
0.6842	Remote Similarity	NPD4756	Discovery
0.6837	Remote Similarity	NPD6435	Approved
0.6837	Remote Similarity	NPD3667	Approved
0.6832	Remote Similarity	NPD3573	Approved
0.6814	Remote Similarity	NPD4634	Approved
0.6807	Remote Similarity	NPD6016	Approved
0.6807	Remote Similarity	NPD5983	Phase 2
0.6807	Remote Similarity	NPD6015	Approved
0.6804	Remote Similarity	NPD4252	Approved
0.6803	Remote Similarity	NPD7078	Approved
0.675	Remote Similarity	NPD5988	Approved
0.675	Remote Similarity	NPD6370	Approved
0.6748	Remote Similarity	NPD7736	Approved
0.6735	Remote Similarity	NPD5369	Approved
0.6733	Remote Similarity	NPD5690	Phase 2
0.6733	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6098	Approved
0.6731	Remote Similarity	NPD7983	Approved
0.6727	Remote Similarity	NPD4754	Approved
0.6723	Remote Similarity	NPD6059	Approved
0.67	Remote Similarity	NPD4786	Approved
0.67	Remote Similarity	NPD4197	Approved
0.6699	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7604	Phase 2
0.6694	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6637	Remote Similarity	NPD5128	Approved
0.6637	Remote Similarity	NPD5168	Approved
0.6637	Remote Similarity	NPD4730	Approved
0.6637	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD7839	Suspended
0.6634	Remote Similarity	NPD5329	Approved
0.6633	Remote Similarity	NPD5368	Approved
0.6607	Remote Similarity	NPD4768	Approved
0.6607	Remote Similarity	NPD4767	Approved
0.6604	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7900	Approved
0.6598	Remote Similarity	NPD3617	Approved
0.6585	Remote Similarity	NPD6336	Discontinued
0.6571	Remote Similarity	NPD5281	Approved
0.6571	Remote Similarity	NPD5284	Approved
0.6569	Remote Similarity	NPD4694	Approved
0.6569	Remote Similarity	NPD5280	Approved
0.6542	Remote Similarity	NPD5654	Approved
0.6522	Remote Similarity	NPD5247	Approved
0.6522	Remote Similarity	NPD5135	Approved
0.6522	Remote Similarity	NPD5249	Phase 3
0.6522	Remote Similarity	NPD5169	Approved
0.6522	Remote Similarity	NPD5251	Approved
0.6522	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5250	Approved
0.6522	Remote Similarity	NPD5248	Approved
0.6509	Remote Similarity	NPD4202	Approved
0.65	Remote Similarity	NPD4221	Approved
0.65	Remote Similarity	NPD4223	Phase 3
0.6491	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7632	Discontinued
0.6476	Remote Similarity	NPD6698	Approved
0.6476	Remote Similarity	NPD46	Approved
0.6466	Remote Similarity	NPD5215	Approved
0.6466	Remote Similarity	NPD5127	Approved
0.6466	Remote Similarity	NPD5216	Approved
0.6466	Remote Similarity	NPD5217	Approved
0.6465	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6008	Approved
0.6442	Remote Similarity	NPD5208	Approved
0.6436	Remote Similarity	NPD6110	Phase 1
0.6429	Remote Similarity	NPD6647	Phase 2
0.6422	Remote Similarity	NPD5959	Approved
0.6415	Remote Similarity	NPD4810	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