NPASS Compound

Structure

NPC472492 OpenBabel07101719152D 22 25 0 0 1 0 0 0 0 0999 V2000 0.4238 2.3837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7472 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2472 -0.0000 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 -0.6236 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.4402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1866 1.5291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0672 0.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8977 1.5031 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6236 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1866 -0.0889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6236 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6236 0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4638 0.6021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8886 1.3689 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5201 0.4236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7988 1.7832 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 20 1 1 0 0 0 13 16 2 0 0 0 0 14 11 1 1 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 1 0 0 0 16 19 1 0 0 0 0 17 21 2 0 0 0 0 19 4 1 1 0 0 0 20 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	332.558
LogP:	4.165
LogD:	3.651
LogS:	-5.466
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.725
Synthetic Accessibility Score:	5.373
Fsp3:	0.85
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:	-4.851
MDCK Permeability:	2.285394111822825e-05
Pgp-inhibitor:	0.834
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.732

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	97.42891693115234%
Volume Distribution (VD):	0.994
Pgp-substrate:	2.9005115032196045%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.677
CYP2C19-inhibitor:	0.202
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.425
CYP2C9-substrate:	0.628
CYP2D6-inhibitor:	0.065
CYP2D6-substrate:	0.535
CYP3A4-inhibitor:	0.644
CYP3A4-substrate:	0.383

ADMET: Excretion

Clearance (CL):	4.255
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.717
Skin Sensitization:	0.602
Carcinogencity:	0.039
Eye Corrosion:	0.006
Eye Irritation:	0.246
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC472492

Natural Product ID:	NPC472492
*Common Name:**	ATPDASPSNNPCMV-JJLDTBFASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ATPDASPSNNPCMV-JJLDTBFASA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-12-17(21)14-11-20(12,22)10-13-6-7-15-18(2,3)8-5-9-19(15,4)16(13)14/h12,14-15,22H,5-11H2,1-4H3/t12-,14+,15-,19-,20-/m1/s1
SMILES:	CC1C(=O)C2CC1(CC3=C2C4(CCCC(C4CC3)(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426500
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO32442	jungermannia fauriana	Species	Jungermanniaceae	Eukaryota	n.a.	Guangxi Zhuang Autonomous Region, China	n.a.	PMID[25856683]

☑ 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	14

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[515632]
NPT2410	Cell Line	NCI-H1299	Homo sapiens	IC50	>	50000.0	nM	PMID[515632]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	50000.0	nM	PMID[515632]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[515632]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	50000.0	nM	PMID[515632]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	50000.0	nM	PMID[515632]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[515632]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[515632]

☑ 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 NPC472492 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	170
0.1-0.2	1580
0.2-0.3	8424
0.3-0.4	15229
0.4-0.5	7089
0.5-0.6	6560
0.6-0.7	2978
0.7-0.8	610
0.8-0.85	43
0.85-0.9	8
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC472494
0.9625	High Similarity	NPC472491
0.9506	High Similarity	NPC472493
0.9375	High Similarity	NPC472480
0.9146	High Similarity	NPC472488
0.9036	High Similarity	NPC472482
0.9036	High Similarity	NPC472484
0.9036	High Similarity	NPC472481
0.8929	High Similarity	NPC472483
0.8824	High Similarity	NPC472489
0.8765	High Similarity	NPC150506
0.869	High Similarity	NPC472479
0.8539	High Similarity	NPC472485
0.8488	Intermediate Similarity	NPC328313
0.8434	Intermediate Similarity	NPC193347
0.8391	Intermediate Similarity	NPC472477
0.8391	Intermediate Similarity	NPC472475
0.8295	Intermediate Similarity	NPC472476
0.8276	Intermediate Similarity	NPC471724
0.8235	Intermediate Similarity	NPC144258
0.8214	Intermediate Similarity	NPC260956
0.8182	Intermediate Similarity	NPC76879
0.8161	Intermediate Similarity	NPC138756
0.814	Intermediate Similarity	NPC474218
0.8118	Intermediate Similarity	NPC477373
0.8118	Intermediate Similarity	NPC477852
0.8101	Intermediate Similarity	NPC144627
0.8095	Intermediate Similarity	NPC201912
0.8095	Intermediate Similarity	NPC38350
0.8072	Intermediate Similarity	NPC215843
0.8068	Intermediate Similarity	NPC53911
0.8068	Intermediate Similarity	NPC471722
0.8046	Intermediate Similarity	NPC72133
0.8043	Intermediate Similarity	NPC95565
0.8023	Intermediate Similarity	NPC59453
0.8023	Intermediate Similarity	NPC82902
0.8023	Intermediate Similarity	NPC221758
0.8	Intermediate Similarity	NPC23434
0.8	Intermediate Similarity	NPC151519
0.8	Intermediate Similarity	NPC150383
0.7978	Intermediate Similarity	NPC472970
0.7978	Intermediate Similarity	NPC472971
0.7978	Intermediate Similarity	NPC54689
0.7952	Intermediate Similarity	NPC476808
0.7935	Intermediate Similarity	NPC473648
0.7935	Intermediate Similarity	NPC263347
0.7927	Intermediate Similarity	NPC92080
0.7912	Intermediate Similarity	NPC243866
0.7912	Intermediate Similarity	NPC25750
0.7907	Intermediate Similarity	NPC168188
0.7907	Intermediate Similarity	NPC83569
0.7907	Intermediate Similarity	NPC470015
0.7907	Intermediate Similarity	NPC69279
0.7889	Intermediate Similarity	NPC136801
0.7889	Intermediate Similarity	NPC69622
0.7882	Intermediate Similarity	NPC147066
0.7865	Intermediate Similarity	NPC242864
0.7865	Intermediate Similarity	NPC143767
0.7865	Intermediate Similarity	NPC131470
0.7857	Intermediate Similarity	NPC472490
0.7857	Intermediate Similarity	NPC477371
0.7841	Intermediate Similarity	NPC145879
0.7841	Intermediate Similarity	NPC89077
0.7841	Intermediate Similarity	NPC469994
0.7841	Intermediate Similarity	NPC20688
0.7841	Intermediate Similarity	NPC474778
0.7841	Intermediate Similarity	NPC474732
0.7841	Intermediate Similarity	NPC28252
0.7841	Intermediate Similarity	NPC474733
0.7841	Intermediate Similarity	NPC55309
0.7841	Intermediate Similarity	NPC118648
0.7841	Intermediate Similarity	NPC51014
0.7841	Intermediate Similarity	NPC31564
0.7841	Intermediate Similarity	NPC222613
0.7841	Intermediate Similarity	NPC475022
0.7841	Intermediate Similarity	NPC94755
0.7816	Intermediate Similarity	NPC473246
0.7816	Intermediate Similarity	NPC58841
0.7816	Intermediate Similarity	NPC329043
0.7816	Intermediate Similarity	NPC161423
0.7816	Intermediate Similarity	NPC227064
0.7816	Intermediate Similarity	NPC209882
0.7816	Intermediate Similarity	NPC321187
0.7791	Intermediate Similarity	NPC133391
0.7791	Intermediate Similarity	NPC469325
0.7791	Intermediate Similarity	NPC110780
0.7789	Intermediate Similarity	NPC110149
0.7778	Intermediate Similarity	NPC326627
0.7778	Intermediate Similarity	NPC32830
0.7778	Intermediate Similarity	NPC86319
0.7778	Intermediate Similarity	NPC2983
0.7778	Intermediate Similarity	NPC119416
0.7778	Intermediate Similarity	NPC474245
0.7778	Intermediate Similarity	NPC310010
0.7778	Intermediate Similarity	NPC275740
0.7778	Intermediate Similarity	NPC477943
0.7766	Intermediate Similarity	NPC472689
0.7766	Intermediate Similarity	NPC472690
0.7766	Intermediate Similarity	NPC477267
0.7766	Intermediate Similarity	NPC477268
0.7765	Intermediate Similarity	NPC469637
0.7765	Intermediate Similarity	NPC476809
0.7753	Intermediate Similarity	NPC159046
0.7753	Intermediate Similarity	NPC136548
0.7753	Intermediate Similarity	NPC317590
0.7753	Intermediate Similarity	NPC233836
0.7753	Intermediate Similarity	NPC99909
0.7753	Intermediate Similarity	NPC187376
0.7753	Intermediate Similarity	NPC475740
0.7753	Intermediate Similarity	NPC58063
0.7753	Intermediate Similarity	NPC96496
0.7753	Intermediate Similarity	NPC165895
0.7742	Intermediate Similarity	NPC241156
0.7742	Intermediate Similarity	NPC469599
0.7742	Intermediate Similarity	NPC45324
0.7742	Intermediate Similarity	NPC127063
0.7742	Intermediate Similarity	NPC69548
0.7742	Intermediate Similarity	NPC48330
0.7742	Intermediate Similarity	NPC162001
0.7742	Intermediate Similarity	NPC184848
0.7742	Intermediate Similarity	NPC200702
0.7742	Intermediate Similarity	NPC222845
0.7738	Intermediate Similarity	NPC207772
0.7738	Intermediate Similarity	NPC30321
0.7727	Intermediate Similarity	NPC102292
0.7727	Intermediate Similarity	NPC123319
0.7727	Intermediate Similarity	NPC473038
0.7727	Intermediate Similarity	NPC94531
0.7727	Intermediate Similarity	NPC469948
0.7727	Intermediate Similarity	NPC474083
0.7727	Intermediate Similarity	NPC197823
0.7727	Intermediate Similarity	NPC311702
0.7717	Intermediate Similarity	NPC66429
0.7717	Intermediate Similarity	NPC470376
0.7717	Intermediate Similarity	NPC474807
0.7717	Intermediate Similarity	NPC233118
0.7717	Intermediate Similarity	NPC472942
0.7717	Intermediate Similarity	NPC152897
0.7717	Intermediate Similarity	NPC134826
0.7717	Intermediate Similarity	NPC470375
0.7717	Intermediate Similarity	NPC206810
0.7717	Intermediate Similarity	NPC250575
0.7708	Intermediate Similarity	NPC473514
0.7701	Intermediate Similarity	NPC476082
0.7701	Intermediate Similarity	NPC278648
0.7692	Intermediate Similarity	NPC191684
0.7692	Intermediate Similarity	NPC171441
0.7692	Intermediate Similarity	NPC183283
0.7692	Intermediate Similarity	NPC478258
0.7692	Intermediate Similarity	NPC478257
0.7692	Intermediate Similarity	NPC469400
0.7692	Intermediate Similarity	NPC320026
0.7684	Intermediate Similarity	NPC186810
0.7674	Intermediate Similarity	NPC14151
0.7674	Intermediate Similarity	NPC477372
0.7667	Intermediate Similarity	NPC328539
0.7667	Intermediate Similarity	NPC193360
0.7667	Intermediate Similarity	NPC44181
0.7667	Intermediate Similarity	NPC474677
0.7667	Intermediate Similarity	NPC320665
0.766	Intermediate Similarity	NPC120708
0.766	Intermediate Similarity	NPC49371
0.766	Intermediate Similarity	NPC155676
0.766	Intermediate Similarity	NPC125622
0.766	Intermediate Similarity	NPC173272
0.764	Intermediate Similarity	NPC212843
0.764	Intermediate Similarity	NPC155011
0.7634	Intermediate Similarity	NPC166906
0.7634	Intermediate Similarity	NPC111015
0.7629	Intermediate Similarity	NPC473424
0.7619	Intermediate Similarity	NPC257666
0.7619	Intermediate Similarity	NPC266193
0.7614	Intermediate Similarity	NPC85774
0.7614	Intermediate Similarity	NPC214043
0.7614	Intermediate Similarity	NPC237712
0.7609	Intermediate Similarity	NPC63748
0.7609	Intermediate Similarity	NPC233116
0.7609	Intermediate Similarity	NPC154101
0.7609	Intermediate Similarity	NPC297265
0.7609	Intermediate Similarity	NPC26888
0.7609	Intermediate Similarity	NPC73457
0.7609	Intermediate Similarity	NPC475806
0.7604	Intermediate Similarity	NPC316964
0.7604	Intermediate Similarity	NPC154072
0.7586	Intermediate Similarity	NPC73882
0.7586	Intermediate Similarity	NPC46881
0.7586	Intermediate Similarity	NPC320514
0.7582	Intermediate Similarity	NPC215029
0.7582	Intermediate Similarity	NPC474570
0.7582	Intermediate Similarity	NPC84271
0.7582	Intermediate Similarity	NPC77168
0.7582	Intermediate Similarity	NPC268406
0.7582	Intermediate Similarity	NPC102414
0.7582	Intermediate Similarity	NPC476733
0.7582	Intermediate Similarity	NPC31985
0.7582	Intermediate Similarity	NPC309603
0.7582	Intermediate Similarity	NPC474889
0.7582	Intermediate Similarity	NPC473999
0.7582	Intermediate Similarity	NPC186688
0.7582	Intermediate Similarity	NPC122116

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 NPC472492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	2114
0.2-0.3	4438
0.3-0.4	1650
0.4-0.5	394
0.5-0.6	146
0.6-0.7	167
0.7-0.8	64
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8765	High Similarity	NPD4692	Approved
0.8765	High Similarity	NPD4139	Approved
0.8471	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD4221	Approved
0.8434	Intermediate Similarity	NPD4223	Phase 3
0.8256	Intermediate Similarity	NPD5690	Phase 2
0.8256	Intermediate Similarity	NPD4694	Approved
0.8256	Intermediate Similarity	NPD5280	Approved
0.8235	Intermediate Similarity	NPD4197	Approved
0.814	Intermediate Similarity	NPD5329	Approved
0.8046	Intermediate Similarity	NPD5205	Approved
0.8046	Intermediate Similarity	NPD4688	Approved
0.8046	Intermediate Similarity	NPD4690	Approved
0.8046	Intermediate Similarity	NPD4689	Approved
0.8046	Intermediate Similarity	NPD4693	Phase 3
0.8046	Intermediate Similarity	NPD4138	Approved
0.8023	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD3667	Approved
0.8	Intermediate Similarity	NPD5284	Approved
0.8	Intermediate Similarity	NPD5281	Approved
0.7952	Intermediate Similarity	NPD3617	Approved
0.7912	Intermediate Similarity	NPD4202	Approved
0.7841	Intermediate Similarity	NPD3618	Phase 1
0.7816	Intermediate Similarity	NPD3133	Approved
0.7816	Intermediate Similarity	NPD3666	Approved
0.7816	Intermediate Similarity	NPD3665	Phase 1
0.7778	Intermediate Similarity	NPD4753	Phase 2
0.7765	Intermediate Similarity	NPD4748	Discontinued
0.7717	Intermediate Similarity	NPD5133	Approved
0.7692	Intermediate Similarity	NPD4096	Approved
0.7667	Intermediate Similarity	NPD4518	Approved
0.7647	Intermediate Similarity	NPD4195	Approved
0.7582	Intermediate Similarity	NPD5328	Approved
0.7579	Intermediate Similarity	NPD4755	Approved
0.7553	Intermediate Similarity	NPD5210	Approved
0.7553	Intermediate Similarity	NPD5695	Phase 3
0.7553	Intermediate Similarity	NPD4629	Approved
0.7527	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4788	Approved
0.75	Intermediate Similarity	NPD5207	Approved
0.75	Intermediate Similarity	NPD5360	Phase 3
0.747	Intermediate Similarity	NPD4784	Approved
0.747	Intermediate Similarity	NPD4785	Approved
0.7444	Intermediate Similarity	NPD5279	Phase 3
0.7444	Intermediate Similarity	NPD6098	Approved
0.7439	Intermediate Similarity	NPD4243	Approved
0.7423	Intermediate Similarity	NPD4700	Approved
0.7423	Intermediate Similarity	NPD4696	Approved
0.7423	Intermediate Similarity	NPD5285	Approved
0.7423	Intermediate Similarity	NPD5286	Approved
0.7419	Intermediate Similarity	NPD6079	Approved
0.7416	Intermediate Similarity	NPD3668	Phase 3
0.7347	Intermediate Similarity	NPD5223	Approved
0.732	Intermediate Similarity	NPD5696	Approved
0.7312	Intermediate Similarity	NPD5692	Phase 3
0.7294	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4697	Phase 3
0.7283	Intermediate Similarity	NPD5208	Approved
0.7273	Intermediate Similarity	NPD5211	Phase 2
0.7273	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD5224	Approved
0.7273	Intermediate Similarity	NPD5225	Approved
0.7273	Intermediate Similarity	NPD4633	Approved
0.7263	Intermediate Similarity	NPD6001	Approved
0.7234	Intermediate Similarity	NPD6050	Approved
0.7234	Intermediate Similarity	NPD5694	Approved
0.7229	Intermediate Similarity	NPD4758	Discontinued
0.7216	Intermediate Similarity	NPD6083	Phase 2
0.7216	Intermediate Similarity	NPD6084	Phase 2
0.7204	Intermediate Similarity	NPD6080	Approved
0.7204	Intermediate Similarity	NPD6904	Approved
0.7204	Intermediate Similarity	NPD6673	Approved
0.72	Intermediate Similarity	NPD5174	Approved
0.72	Intermediate Similarity	NPD4754	Approved
0.72	Intermediate Similarity	NPD5175	Approved
0.7188	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5275	Approved
0.7176	Intermediate Similarity	NPD4190	Phase 3
0.7159	Intermediate Similarity	NPD4695	Discontinued
0.7129	Intermediate Similarity	NPD5141	Approved
0.7115	Intermediate Similarity	NPD4634	Approved
0.7113	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5222	Approved
0.7113	Intermediate Similarity	NPD5221	Approved
0.7108	Intermediate Similarity	NPD4747	Approved
0.71	Intermediate Similarity	NPD5091	Approved
0.7065	Intermediate Similarity	NPD4623	Approved
0.7065	Intermediate Similarity	NPD6409	Approved
0.7065	Intermediate Similarity	NPD4519	Discontinued
0.7065	Intermediate Similarity	NPD6684	Approved
0.7065	Intermediate Similarity	NPD7146	Approved
0.7065	Intermediate Similarity	NPD5330	Approved
0.7065	Intermediate Similarity	NPD7521	Approved
0.7065	Intermediate Similarity	NPD7334	Approved
0.7059	Intermediate Similarity	NPD4768	Approved
0.7059	Intermediate Similarity	NPD6675	Approved
0.7059	Intermediate Similarity	NPD7128	Approved
0.7059	Intermediate Similarity	NPD6402	Approved
0.7059	Intermediate Similarity	NPD4767	Approved
0.7059	Intermediate Similarity	NPD5733	Approved
0.7059	Intermediate Similarity	NPD5739	Approved
0.7059	Intermediate Similarity	NPD4687	Approved
0.7053	Intermediate Similarity	NPD5693	Phase 1
0.7041	Intermediate Similarity	NPD5173	Approved
0.7024	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5276	Approved
0.7024	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6373	Approved
0.7019	Intermediate Similarity	NPD6372	Approved
0.701	Intermediate Similarity	NPD5654	Approved
0.699	Remote Similarity	NPD5697	Approved
0.699	Remote Similarity	NPD5701	Approved
0.6988	Remote Similarity	NPD4137	Phase 3
0.6988	Remote Similarity	NPD3698	Phase 2
0.6988	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7339	Approved
0.6977	Remote Similarity	NPD6942	Approved
0.6957	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4729	Approved
0.6923	Remote Similarity	NPD5128	Approved
0.6923	Remote Similarity	NPD6881	Approved
0.6923	Remote Similarity	NPD4730	Approved
0.6923	Remote Similarity	NPD6899	Approved
0.6923	Remote Similarity	NPD7320	Approved
0.6923	Remote Similarity	NPD6011	Approved
0.6915	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6903	Approved
0.6914	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4245	Approved
0.6905	Remote Similarity	NPD4244	Approved
0.6905	Remote Similarity	NPD4691	Approved
0.6893	Remote Similarity	NPD6008	Approved
0.6887	Remote Similarity	NPD6650	Approved
0.6887	Remote Similarity	NPD6649	Approved
0.6869	Remote Similarity	NPD5959	Approved
0.6867	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6013	Approved
0.6857	Remote Similarity	NPD6012	Approved
0.6857	Remote Similarity	NPD6014	Approved
0.6842	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4224	Phase 2
0.6809	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5250	Approved
0.6792	Remote Similarity	NPD5169	Approved
0.6792	Remote Similarity	NPD5251	Approved
0.6792	Remote Similarity	NPD6883	Approved
0.6792	Remote Similarity	NPD7102	Approved
0.6792	Remote Similarity	NPD5135	Approved
0.6792	Remote Similarity	NPD5248	Approved
0.6792	Remote Similarity	NPD5249	Phase 3
0.6792	Remote Similarity	NPD7290	Approved
0.6792	Remote Similarity	NPD5247	Approved
0.6782	Remote Similarity	NPD3702	Approved
0.6778	Remote Similarity	NPD7525	Registered
0.6742	Remote Similarity	NPD5364	Discontinued
0.6737	Remote Similarity	NPD5737	Approved
0.6737	Remote Similarity	NPD6672	Approved
0.6729	Remote Similarity	NPD6869	Approved
0.6729	Remote Similarity	NPD6847	Approved
0.6729	Remote Similarity	NPD5216	Approved
0.6729	Remote Similarity	NPD5217	Approved
0.6729	Remote Similarity	NPD6617	Approved
0.6729	Remote Similarity	NPD8130	Phase 1
0.6729	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5127	Approved
0.6729	Remote Similarity	NPD5215	Approved
0.6727	Remote Similarity	NPD7115	Discovery
0.6707	Remote Similarity	NPD7341	Phase 2
0.6706	Remote Similarity	NPD4789	Approved
0.6703	Remote Similarity	NPD5369	Approved
0.6701	Remote Similarity	NPD7515	Phase 2
0.6701	Remote Similarity	NPD8035	Phase 2
0.6701	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD4058	Approved
0.6632	Remote Similarity	NPD3573	Approved
0.6628	Remote Similarity	NPD6081	Approved
0.6606	Remote Similarity	NPD4632	Approved
0.6591	Remote Similarity	NPD3703	Phase 2
0.6566	Remote Similarity	NPD7748	Approved
0.6549	Remote Similarity	NPD6054	Approved
0.6549	Remote Similarity	NPD6059	Approved
0.6549	Remote Similarity	NPD6319	Approved
0.6545	Remote Similarity	NPD5167	Approved
0.6538	Remote Similarity	NPD6052	Approved
0.6535	Remote Similarity	NPD7902	Approved
0.6531	Remote Similarity	NPD6411	Approved
0.6517	Remote Similarity	NPD6117	Approved
0.6491	Remote Similarity	NPD6016	Approved
0.6491	Remote Similarity	NPD6015	Approved
0.6486	Remote Similarity	NPD6274	Approved
0.6477	Remote Similarity	NPD6924	Approved
0.6477	Remote Similarity	NPD6926	Approved
0.6452	Remote Similarity	NPD4269	Approved
0.6452	Remote Similarity	NPD4270	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data