NPASS Compound

Structure

CID17432 OpenBabel06191715342D 43 46 0 0 1 0 0 0 0 0999 V2000 0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -6.5000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 0.0000 -5.0000 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 4.3301 -0.5000 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 0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 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 4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 39 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 8 9 1 0 0 0 0 8 12 2 0 0 0 0 9 15 1 0 0 0 0 10 30 1 0 0 0 0 11 31 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 18 1 0 0 0 0 15 25 2 0 0 0 0 16 10 1 6 0 0 0 16 19 1 0 0 0 0 16 40 1 0 0 0 0 17 11 1 1 0 0 0 17 20 1 0 0 0 0 17 41 1 0 0 0 0 18 26 2 0 0 0 0 18 27 1 0 0 0 0 19 21 1 0 0 0 0 19 32 1 1 0 0 0 20 22 1 0 0 0 0 20 33 1 6 0 0 0 21 23 1 0 0 0 0 21 34 1 6 0 0 0 22 24 1 0 0 0 0 22 35 1 1 0 0 0 23 28 1 0 0 0 0 23 36 1 1 0 0 0 24 29 1 0 0 0 0 24 37 1 6 0 0 0 25 42 1 0 0 0 0 26 43 1 0 0 0 0 27 38 2 0 0 0 0 27 39 1 0 0 0 0 28 40 1 0 0 0 0 28 42 1 6 0 0 0 29 41 1 0 0 0 0 29 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.23
Volume:	580.522
LogP:	1.111
LogD:	0.216
LogS:	-2.614
# Rotatable Bonds:	10
TPSA:	225.06
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.119
Synthetic Accessibility Score:	4.766
Fsp3:	0.552
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.353
MDCK Permeability:	5.704517388949171e-05
Pgp-inhibitor:	0.144
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.92
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	63.59034729003906%
Volume Distribution (VD):	0.534
Pgp-substrate:	11.763940811157227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.238
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.011

ADMET: Excretion

Clearance (CL):	1.417
Half-life (T1/2):	0.607

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.812
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.127
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC17432

Natural Product ID:	NPC17432
*Common Name:**	2-Carbomethoxy-3-Prenyl-1,4-Naphthohydroquinone-1,4-Di-O-Beta-Glucoside
IUPAC Name:	methyl 3-(3-methylbut-2-enyl)-1,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]naphthalene-2-carboxylate
Synonyms:
Standard InCHIKey:	OZDABLANSWPSGY-GIQZDESDSA-N
Standard InCHI:	InChI=1S/C29H38O14/c1-12(2)8-9-15-18(27(38)39-3)26(43-29-24(37)22(35)20(33)17(11-31)41-29)14-7-5-4-6-13(14)25(15)42-28-23(36)21(34)19(32)16(10-30)40-28/h4-8,16-17,19-24,28-37H,9-11H2,1-3H3/t16-,17-,19-,20-,21+,22+,23-,24-,28+,29+/m1/s1
SMILES:	CC(=CCc1c(c(c2ccccc2c1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510252
PubChem CID:	10031663
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO12604	Phakellia dendyi	Species	Bubaridae	Eukaryota	n.a.	Byron Strait, Papua New Guinea	2003	PMID[18327911]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176404]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12604	Phakellia dendyi	Species	Bubaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1540	Scopolia tangutica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6819	Cardopatium corymbosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3034	Lonchocarpus yucatanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7081	Sidastrum tehuacanum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3220	Aberia caffra	n.a.	n.a.	n.a.	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
Others	4

Activity Type	# Activity
CELL-LINE	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	91.3	%	PMID[555672]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	86.9	%	PMID[555672]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	81.2	%	PMID[555672]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	90.3	%	PMID[555672]

☑ 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 NPC17432 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	374
0.1-0.2	1451
0.2-0.3	3113
0.3-0.4	7258
0.4-0.5	10131
0.5-0.6	6431
0.6-0.7	6829
0.7-0.8	6473
0.8-0.85	506
0.85-0.9	122
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC246274
0.9217	High Similarity	NPC245059
0.9217	High Similarity	NPC84494
0.9193	High Similarity	NPC178281
0.9162	High Similarity	NPC470452
0.9162	High Similarity	NPC470453
0.9162	High Similarity	NPC164047
0.9162	High Similarity	NPC470448
0.9152	High Similarity	NPC470454
0.9152	High Similarity	NPC199533
0.9146	High Similarity	NPC315619
0.9112	High Similarity	NPC241847
0.9096	High Similarity	NPC102053
0.908	High Similarity	NPC63470
0.9068	High Similarity	NPC146837
0.9068	High Similarity	NPC216752
0.9068	High Similarity	NPC278329
0.9036	High Similarity	NPC63105
0.8988	High Similarity	NPC58538
0.8982	High Similarity	NPC198893
0.8982	High Similarity	NPC314489
0.8982	High Similarity	NPC232818
0.8976	High Similarity	NPC203751
0.8957	High Similarity	NPC99216
0.8951	High Similarity	NPC101116
0.8951	High Similarity	NPC212099
0.8944	High Similarity	NPC328093
0.8938	High Similarity	NPC177742
0.8935	High Similarity	NPC475161
0.8935	High Similarity	NPC477860
0.8922	High Similarity	NPC186800
0.8922	High Similarity	NPC470667
0.8869	High Similarity	NPC92403
0.8869	High Similarity	NPC66820
0.8869	High Similarity	NPC170018
0.8869	High Similarity	NPC76112
0.8869	High Similarity	NPC289876
0.8868	High Similarity	NPC185103
0.8862	High Similarity	NPC213052
0.8862	High Similarity	NPC85368
0.8855	High Similarity	NPC298778
0.8855	High Similarity	NPC241874
0.883	High Similarity	NPC224557
0.883	High Similarity	NPC292706
0.881	High Similarity	NPC307754
0.881	High Similarity	NPC223735
0.881	High Similarity	NPC68381
0.8802	High Similarity	NPC471921
0.8802	High Similarity	NPC20114
0.8802	High Similarity	NPC114550
0.8802	High Similarity	NPC129930
0.8802	High Similarity	NPC474075
0.8802	High Similarity	NPC471920
0.8802	High Similarity	NPC471922
0.8802	High Similarity	NPC292712
0.8802	High Similarity	NPC312006
0.8795	High Similarity	NPC259905
0.8795	High Similarity	NPC473202
0.8788	High Similarity	NPC178851
0.8765	High Similarity	NPC161609
0.8765	High Similarity	NPC275690
0.8757	High Similarity	NPC475246
0.8757	High Similarity	NPC46958
0.875	High Similarity	NPC260604
0.875	High Similarity	NPC299435
0.875	High Similarity	NPC230439
0.875	High Similarity	NPC92153
0.875	High Similarity	NPC279281
0.875	High Similarity	NPC299761
0.8743	High Similarity	NPC52598
0.8735	High Similarity	NPC298847
0.8735	High Similarity	NPC249977
0.872	High Similarity	NPC61594
0.872	High Similarity	NPC56735
0.8713	High Similarity	NPC197357
0.8713	High Similarity	NPC85316
0.8706	High Similarity	NPC35266
0.8704	High Similarity	NPC208651
0.8704	High Similarity	NPC206641
0.8698	High Similarity	NPC474345
0.8698	High Similarity	NPC3718
0.869	High Similarity	NPC76128
0.869	High Similarity	NPC111536
0.869	High Similarity	NPC30432
0.869	High Similarity	NPC5029
0.869	High Similarity	NPC271385
0.8688	High Similarity	NPC215811
0.8686	High Similarity	NPC48474
0.8671	High Similarity	NPC87583
0.8667	High Similarity	NPC147596
0.8663	High Similarity	NPC476203
0.8662	High Similarity	NPC211565
0.8659	High Similarity	NPC132737
0.8655	High Similarity	NPC114257
0.8655	High Similarity	NPC299149
0.8655	High Similarity	NPC277710
0.8655	High Similarity	NPC153578
0.865	High Similarity	NPC53139
0.8644	High Similarity	NPC314687
0.8642	High Similarity	NPC148323
0.8642	High Similarity	NPC283480
0.8639	High Similarity	NPC199357
0.8634	High Similarity	NPC470331
0.8631	High Similarity	NPC313304
0.8631	High Similarity	NPC199079
0.8631	High Similarity	NPC210808
0.8629	High Similarity	NPC314672
0.8614	High Similarity	NPC7752
0.8613	High Similarity	NPC114120
0.8613	High Similarity	NPC167045
0.8608	High Similarity	NPC92054
0.8608	High Similarity	NPC83975
0.8608	High Similarity	NPC140722
0.8608	High Similarity	NPC4958
0.8606	High Similarity	NPC473961
0.8606	High Similarity	NPC22324
0.8588	High Similarity	NPC146803
0.858	High Similarity	NPC192219
0.858	High Similarity	NPC472386
0.858	High Similarity	NPC174599
0.858	High Similarity	NPC137871
0.858	High Similarity	NPC288152
0.858	High Similarity	NPC82190
0.858	High Similarity	NPC9002
0.858	High Similarity	NPC257011
0.858	High Similarity	NPC183441
0.858	High Similarity	NPC3449
0.8571	High Similarity	NPC191653
0.8571	High Similarity	NPC183536
0.8571	High Similarity	NPC222455
0.8571	High Similarity	NPC34965
0.8563	High Similarity	NPC229817
0.8563	High Similarity	NPC475352
0.8563	High Similarity	NPC473686
0.8563	High Similarity	NPC475220
0.8563	High Similarity	NPC221140
0.8563	High Similarity	NPC70441
0.8563	High Similarity	NPC178173
0.8562	High Similarity	NPC93619
0.8555	High Similarity	NPC475662
0.8555	High Similarity	NPC293227
0.8555	High Similarity	NPC473717
0.8555	High Similarity	NPC473631
0.8554	High Similarity	NPC127415
0.8545	High Similarity	NPC217950
0.8544	High Similarity	NPC60389
0.8538	High Similarity	NPC312630
0.8538	High Similarity	NPC324220
0.8538	High Similarity	NPC475233
0.8537	High Similarity	NPC57072
0.8537	High Similarity	NPC231475
0.8537	High Similarity	NPC186113
0.8529	High Similarity	NPC472054
0.8529	High Similarity	NPC184624
0.8521	High Similarity	NPC477571
0.8521	High Similarity	NPC477572
0.8521	High Similarity	NPC251144
0.8521	High Similarity	NPC241387
0.8521	High Similarity	NPC477573
0.8521	High Similarity	NPC293004
0.8519	High Similarity	NPC477691
0.8519	High Similarity	NPC205172
0.8519	High Similarity	NPC209393
0.8514	High Similarity	NPC105591
0.8514	High Similarity	NPC286301
0.8514	High Similarity	NPC313063
0.8512	High Similarity	NPC475453
0.8512	High Similarity	NPC473531
0.8503	High Similarity	NPC478026
0.85	High Similarity	NPC131405
0.8494	Intermediate Similarity	NPC97637
0.8494	Intermediate Similarity	NPC187934
0.8491	Intermediate Similarity	NPC472339
0.8488	Intermediate Similarity	NPC477683
0.8488	Intermediate Similarity	NPC477682
0.8485	Intermediate Similarity	NPC470358
0.848	Intermediate Similarity	NPC193377
0.8476	Intermediate Similarity	NPC474441
0.8476	Intermediate Similarity	NPC476026
0.8476	Intermediate Similarity	NPC474398
0.8476	Intermediate Similarity	NPC474401
0.8475	Intermediate Similarity	NPC264302
0.8471	Intermediate Similarity	NPC473697
0.8471	Intermediate Similarity	NPC475155
0.8466	Intermediate Similarity	NPC205721
0.8462	Intermediate Similarity	NPC472381
0.8462	Intermediate Similarity	NPC472383
0.8457	Intermediate Similarity	NPC477690
0.8457	Intermediate Similarity	NPC281272
0.8452	Intermediate Similarity	NPC471923
0.8448	Intermediate Similarity	NPC473883
0.8443	Intermediate Similarity	NPC477689
0.8443	Intermediate Similarity	NPC124155
0.8443	Intermediate Similarity	NPC257566
0.8439	Intermediate Similarity	NPC212290
0.8436	Intermediate Similarity	NPC470195
0.8436	Intermediate Similarity	NPC470196
0.8436	Intermediate Similarity	NPC470197
0.8436	Intermediate Similarity	NPC282474
0.8436	Intermediate Similarity	NPC470198

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 NPC17432 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	886
0.2-0.3	1612
0.3-0.4	2662
0.4-0.5	2103
0.5-0.6	1062
0.6-0.7	365
0.7-0.8	127
0.8-0.85	14
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8869	High Similarity	NPD8313	Approved
0.8869	High Similarity	NPD8312	Approved
0.8621	High Similarity	NPD7879	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6559	Discontinued
0.8293	Intermediate Similarity	NPD8455	Phase 2
0.8269	Intermediate Similarity	NPD2346	Discontinued
0.8246	Intermediate Similarity	NPD5844	Phase 1
0.8246	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7783	Phase 2
0.8198	Intermediate Similarity	NPD7074	Phase 3
0.8192	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7819	Suspended
0.8161	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8152	Intermediate Similarity	NPD7435	Discontinued
0.8144	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD7054	Approved
0.8133	Intermediate Similarity	NPD5402	Approved
0.8092	Intermediate Similarity	NPD7472	Approved
0.8049	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD6823	Phase 2
0.8	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7989	Intermediate Similarity	NPD6777	Approved
0.7989	Intermediate Similarity	NPD6781	Approved
0.7989	Intermediate Similarity	NPD6776	Approved
0.7989	Intermediate Similarity	NPD6782	Approved
0.7989	Intermediate Similarity	NPD6778	Approved
0.7989	Intermediate Similarity	NPD6780	Approved
0.7989	Intermediate Similarity	NPD6779	Approved
0.7964	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD7698	Approved
0.7957	Intermediate Similarity	NPD7696	Phase 3
0.7957	Intermediate Similarity	NPD7697	Approved
0.7955	Intermediate Similarity	NPD7808	Phase 3
0.7953	Intermediate Similarity	NPD6232	Discontinued
0.7943	Intermediate Similarity	NPD6797	Phase 2
0.7929	Intermediate Similarity	NPD7075	Discontinued
0.7919	Intermediate Similarity	NPD7473	Discontinued
0.7895	Intermediate Similarity	NPD7874	Approved
0.7895	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7884	Intermediate Similarity	NPD7701	Phase 2
0.788	Intermediate Similarity	NPD7699	Phase 2
0.788	Intermediate Similarity	NPD7700	Phase 2
0.7874	Intermediate Similarity	NPD3818	Discontinued
0.7874	Intermediate Similarity	NPD7228	Approved
0.7842	Intermediate Similarity	NPD8151	Discontinued
0.7836	Intermediate Similarity	NPD5494	Approved
0.7819	Intermediate Similarity	NPD7870	Phase 2
0.7819	Intermediate Similarity	NPD7871	Phase 2
0.7814	Intermediate Similarity	NPD6534	Approved
0.7814	Intermediate Similarity	NPD6535	Approved
0.7784	Intermediate Similarity	NPD4380	Phase 2
0.7778	Intermediate Similarity	NPD8150	Discontinued
0.776	Intermediate Similarity	NPD6212	Phase 3
0.776	Intermediate Similarity	NPD6213	Phase 3
0.776	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2935	Discontinued
0.7746	Intermediate Similarity	NPD3787	Discontinued
0.7716	Intermediate Similarity	NPD6674	Discontinued
0.7711	Intermediate Similarity	NPD5403	Approved
0.7697	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2533	Approved
0.7697	Intermediate Similarity	NPD5401	Approved
0.7697	Intermediate Similarity	NPD2534	Approved
0.7697	Intermediate Similarity	NPD2532	Approved
0.7697	Intermediate Similarity	NPD7240	Approved
0.7692	Intermediate Similarity	NPD6801	Discontinued
0.7692	Intermediate Similarity	NPD37	Approved
0.767	Intermediate Similarity	NPD3751	Discontinued
0.7669	Intermediate Similarity	NPD4628	Phase 3
0.7668	Intermediate Similarity	NPD7801	Approved
0.7661	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4966	Approved
0.7661	Intermediate Similarity	NPD7768	Phase 2
0.7661	Intermediate Similarity	NPD4967	Phase 2
0.7661	Intermediate Similarity	NPD4965	Approved
0.7657	Intermediate Similarity	NPD6166	Phase 2
0.7657	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2313	Discontinued
0.7643	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7411	Suspended
0.7632	Intermediate Similarity	NPD8319	Approved
0.7632	Intermediate Similarity	NPD8320	Phase 1
0.7602	Intermediate Similarity	NPD3817	Phase 2
0.7602	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD1934	Approved
0.7574	Intermediate Similarity	NPD6599	Discontinued
0.7572	Intermediate Similarity	NPD6234	Discontinued
0.7544	Intermediate Similarity	NPD1465	Phase 2
0.7544	Intermediate Similarity	NPD2801	Approved
0.7516	Intermediate Similarity	NPD6832	Phase 2
0.7515	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7199	Phase 2
0.7469	Intermediate Similarity	NPD2799	Discontinued
0.7458	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6799	Approved
0.7423	Intermediate Similarity	NPD5406	Approved
0.7423	Intermediate Similarity	NPD5408	Approved
0.7423	Intermediate Similarity	NPD5404	Approved
0.7423	Intermediate Similarity	NPD1551	Phase 2
0.7423	Intermediate Similarity	NPD5405	Approved
0.7421	Intermediate Similarity	NPD7985	Registered
0.7403	Intermediate Similarity	NPD7685	Pre-registration
0.7391	Intermediate Similarity	NPD8434	Phase 2
0.7384	Intermediate Similarity	NPD6844	Discontinued
0.7381	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7266	Discontinued
0.7368	Intermediate Similarity	NPD8285	Discontinued
0.7353	Intermediate Similarity	NPD1653	Approved
0.7349	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3750	Approved
0.7349	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6273	Approved
0.7317	Intermediate Similarity	NPD2438	Suspended
0.7314	Intermediate Similarity	NPD3749	Approved
0.7303	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7930	Approved
0.7284	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD447	Suspended
0.7278	Intermediate Similarity	NPD7177	Discontinued
0.7278	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5763	Approved
0.7273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5762	Approved
0.7256	Intermediate Similarity	NPD3748	Approved
0.7247	Intermediate Similarity	NPD5711	Approved
0.7247	Intermediate Similarity	NPD5710	Approved
0.7246	Intermediate Similarity	NPD7003	Approved
0.7246	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7999	Approved
0.7231	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1549	Phase 2
0.7229	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2796	Approved
0.7195	Intermediate Similarity	NPD7097	Phase 1
0.7191	Intermediate Similarity	NPD8127	Discontinued
0.7179	Intermediate Similarity	NPD1611	Approved
0.7179	Intermediate Similarity	NPD1091	Approved
0.7178	Intermediate Similarity	NPD6355	Discontinued
0.717	Intermediate Similarity	NPD2798	Approved
0.716	Intermediate Similarity	NPD6233	Phase 2
0.7159	Intermediate Similarity	NPD3882	Suspended
0.7152	Intermediate Similarity	NPD1283	Approved
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7152	Intermediate Similarity	NPD4308	Phase 3
0.7151	Intermediate Similarity	NPD7229	Phase 3
0.715	Intermediate Similarity	NPD8059	Phase 3
0.715	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1511	Approved
0.7117	Intermediate Similarity	NPD4060	Phase 1
0.7117	Intermediate Similarity	NPD2979	Phase 3
0.7107	Intermediate Similarity	NPD7584	Approved
0.7107	Intermediate Similarity	NPD1203	Approved
0.7107	Intermediate Similarity	NPD2797	Approved
0.7099	Intermediate Similarity	NPD411	Approved
0.7099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6798	Discontinued
0.7098	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD920	Approved
0.707	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6004	Phase 3
0.7066	Intermediate Similarity	NPD6005	Phase 3
0.7066	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6002	Phase 3
0.7051	Intermediate Similarity	NPD5125	Phase 3
0.7051	Intermediate Similarity	NPD5126	Approved
0.7041	Intermediate Similarity	NPD7680	Approved
0.7035	Intermediate Similarity	NPD1512	Approved
0.7029	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD9717	Approved
0.7025	Intermediate Similarity	NPD1608	Approved
0.702	Intermediate Similarity	NPD7583	Approved
0.7018	Intermediate Similarity	NPD7390	Discontinued
0.7012	Intermediate Similarity	NPD4307	Phase 2
0.7006	Intermediate Similarity	NPD6100	Approved
0.7006	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD1247	Approved
0.6995	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7799	Discontinued
0.6994	Remote Similarity	NPD3268	Approved
0.6985	Remote Similarity	NPD7585	Approved
0.6983	Remote Similarity	NPD919	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