NPASS Compound

Structure

NPC44004 OpenBabel07101719142D 26 30 0 0 1 0 0 0 0 0999 V2000 -3.7399 1.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1099 -2.8011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7015 -0.1623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1782 0.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7872 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9695 0.8377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4451 1.0151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2922 -2.2255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4563 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1034 -0.6623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8736 1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2772 -1.2256 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9563 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3216 -0.9309 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3458 -2.5487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8355 -0.6623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8355 0.3377 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0076 1.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0511 -3.5043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7015 -1.1623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8355 1.3377 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 -4.9695 -1.1623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7460 -1.7486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 9 2 0 0 0 0 4 8 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 18 1 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 10 1 0 0 0 0 9 16 1 0 0 0 0 10 5 1 6 0 0 0 10 14 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 1 0 0 0 12 19 1 6 0 0 0 12 20 1 0 0 0 0 13 9 1 6 0 0 0 13 15 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 6 0 0 0 15 26 1 1 0 0 0 16 21 2 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 17 25 1 0 0 0 0 18 3 1 6 0 0 0 18 23 1 0 0 0 0 19 7 1 6 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.14
Volume:	345.384
LogP:	1.2
LogD:	1.485
LogS:	-3.547
# Rotatable Bonds:	3
TPSA:	97.89
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.331
Synthetic Accessibility Score:	5.697
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.298
MDCK Permeability:	7.367337093455717e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.442
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.645
Plasma Protein Binding (PPB):	50.15611267089844%
Volume Distribution (VD):	0.907
Pgp-substrate:	50.777400970458984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.568
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.231
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	9.531
Half-life (T1/2):	0.477

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.533
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.524
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.466
Carcinogencity:	0.9
Eye Corrosion:	0.028
Eye Irritation:	0.073
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC44004

Natural Product ID:	NPC44004
*Common Name:**	Repin
IUPAC Name:	[(3aR,4S,6aR,8S,9R,9aS,9bS)-8-hydroxy-3,6-dimethylidene-2-oxospiro[3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-9,2'-oxirane]-4-yl] (2S)-2-methyloxirane-2-carboxylate
Synonyms:	Repin
Standard InCHIKey:	HQZJODBJOBTCPI-BQPPTCRNSA-N
Standard InCHI:	InChI=1S/C19H22O7/c1-8-4-11(25-17(22)18(3)6-23-18)13-9(2)16(21)26-15(13)14-10(8)5-12(20)19(14)7-24-19/h10-15,20H,1-2,4-7H2,3H3/t10-,11-,12-,13+,14-,15-,18-,19+/m0/s1
SMILES:	C=C1C[C@@H]([C@H]2C(=C)C(=O)O[C@@H]2[C@@H]2[C@H]1C[C@@H]([C@@]12CO1)O)OC(=O)[C@]1(C)CO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485807
PubChem CID:	14466529
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO30807	Acroptilon repens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2348202]
NPO30807	Acroptilon repens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30807	Acroptilon repens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	8
Others	1

Activity Type	# Activity
Cell Line	6
CELL-LINE	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT309	Cell Line	1A9	Homo sapiens	IC50	=	300.0	nM	PMID[527255]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	800.0	nM	PMID[527255]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1100.0	nM	PMID[527255]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1400.0	nM	PMID[527255]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2500.0	nM	PMID[527255]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	2500.0	nM	PMID[527255]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	9240.0	nM	PMID[527253]
NPT2	Others	Unspecified		Inhibition	=	50.0	%	PMID[527254]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	800.0	nM	PMID[527255]

☑ 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 NPC44004 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	322
0.1-0.2	2379
0.2-0.3	7565
0.3-0.4	15337
0.4-0.5	9213
0.5-0.6	5705
0.6-0.7	1752
0.7-0.8	369
0.8-0.85	39
0.85-0.9	13
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9184	High Similarity	NPC45125
0.9082	High Similarity	NPC474313
0.89	High Similarity	NPC471381
0.89	High Similarity	NPC186861
0.8878	High Similarity	NPC472873
0.8762	High Similarity	NPC139838
0.8762	High Similarity	NPC59489
0.87	High Similarity	NPC471150
0.87	High Similarity	NPC311904
0.8673	High Similarity	NPC475788
0.8654	High Similarity	NPC54737
0.8571	High Similarity	NPC155215
0.8571	High Similarity	NPC184063
0.8557	High Similarity	NPC215556
0.85	High Similarity	NPC163228
0.8491	Intermediate Similarity	NPC68248
0.8485	Intermediate Similarity	NPC258216
0.8469	Intermediate Similarity	NPC19087
0.8469	Intermediate Similarity	NPC216284
0.8454	Intermediate Similarity	NPC79549
0.8416	Intermediate Similarity	NPC476009
0.8367	Intermediate Similarity	NPC472872
0.8367	Intermediate Similarity	NPC38392
0.8365	Intermediate Similarity	NPC471148
0.8333	Intermediate Similarity	NPC181151
0.8318	Intermediate Similarity	NPC117604
0.8317	Intermediate Similarity	NPC476053
0.8317	Intermediate Similarity	NPC475900
0.8283	Intermediate Similarity	NPC54065
0.8283	Intermediate Similarity	NPC297474
0.8265	Intermediate Similarity	NPC207114
0.8265	Intermediate Similarity	NPC217983
0.8235	Intermediate Similarity	NPC142529
0.8235	Intermediate Similarity	NPC91771
0.8224	Intermediate Similarity	NPC26617
0.8218	Intermediate Similarity	NPC473331
0.82	Intermediate Similarity	NPC171360
0.82	Intermediate Similarity	NPC293001
0.82	Intermediate Similarity	NPC35959
0.82	Intermediate Similarity	NPC63193
0.82	Intermediate Similarity	NPC133888
0.82	Intermediate Similarity	NPC57304
0.82	Intermediate Similarity	NPC29821
0.8182	Intermediate Similarity	NPC155935
0.8144	Intermediate Similarity	NPC284534
0.8144	Intermediate Similarity	NPC204105
0.8144	Intermediate Similarity	NPC300082
0.8142	Intermediate Similarity	NPC475401
0.8131	Intermediate Similarity	NPC243998
0.8119	Intermediate Similarity	NPC473263
0.8119	Intermediate Similarity	NPC473234
0.8119	Intermediate Similarity	NPC308656
0.8119	Intermediate Similarity	NPC472874
0.8119	Intermediate Similarity	NPC60386
0.8119	Intermediate Similarity	NPC473273
0.8113	Intermediate Similarity	NPC473148
0.81	Intermediate Similarity	NPC35809
0.8095	Intermediate Similarity	NPC150923
0.807	Intermediate Similarity	NPC477092
0.8061	Intermediate Similarity	NPC304558
0.8061	Intermediate Similarity	NPC187661
0.8056	Intermediate Similarity	NPC477513
0.8053	Intermediate Similarity	NPC475305
0.8037	Intermediate Similarity	NPC474741
0.8036	Intermediate Similarity	NPC121816
0.802	Intermediate Similarity	NPC475881
0.802	Intermediate Similarity	NPC70251
0.8019	Intermediate Similarity	NPC474747
0.8	Intermediate Similarity	NPC70865
0.7981	Intermediate Similarity	NPC161493
0.798	Intermediate Similarity	NPC270270
0.7965	Intermediate Similarity	NPC255450
0.7965	Intermediate Similarity	NPC170692
0.7963	Intermediate Similarity	NPC223450
0.7963	Intermediate Similarity	NPC474101
0.7961	Intermediate Similarity	NPC67584
0.7961	Intermediate Similarity	NPC52044
0.7961	Intermediate Similarity	NPC213698
0.7946	Intermediate Similarity	NPC273242
0.7944	Intermediate Similarity	NPC475945
0.7944	Intermediate Similarity	NPC475871
0.7941	Intermediate Similarity	NPC153590
0.7941	Intermediate Similarity	NPC200237
0.7938	Intermediate Similarity	NPC245665
0.7938	Intermediate Similarity	NPC111409
0.7925	Intermediate Similarity	NPC474339
0.7925	Intermediate Similarity	NPC164598
0.7925	Intermediate Similarity	NPC201718
0.7925	Intermediate Similarity	NPC471767
0.7925	Intermediate Similarity	NPC171759
0.7921	Intermediate Similarity	NPC246173
0.7909	Intermediate Similarity	NPC115352
0.7905	Intermediate Similarity	NPC49833
0.7905	Intermediate Similarity	NPC249171
0.7905	Intermediate Similarity	NPC221615
0.79	Intermediate Similarity	NPC178875
0.7885	Intermediate Similarity	NPC76862
0.7885	Intermediate Similarity	NPC39859
0.7885	Intermediate Similarity	NPC470883
0.7885	Intermediate Similarity	NPC24956
0.7885	Intermediate Similarity	NPC213078
0.7885	Intermediate Similarity	NPC158416
0.7885	Intermediate Similarity	NPC18019
0.7879	Intermediate Similarity	NPC56593
0.7879	Intermediate Similarity	NPC470242
0.7864	Intermediate Similarity	NPC127019
0.7864	Intermediate Similarity	NPC198853
0.7864	Intermediate Similarity	NPC190294
0.7857	Intermediate Similarity	NPC194859
0.7857	Intermediate Similarity	NPC224386
0.7857	Intermediate Similarity	NPC475924
0.7857	Intermediate Similarity	NPC475851
0.785	Intermediate Similarity	NPC250594
0.785	Intermediate Similarity	NPC86077
0.7843	Intermediate Similarity	NPC286341
0.7843	Intermediate Similarity	NPC133698
0.7843	Intermediate Similarity	NPC469627
0.7843	Intermediate Similarity	NPC131209
0.7843	Intermediate Similarity	NPC475925
0.7843	Intermediate Similarity	NPC191339
0.7835	Intermediate Similarity	NPC246076
0.7822	Intermediate Similarity	NPC173926
0.781	Intermediate Similarity	NPC471140
0.781	Intermediate Similarity	NPC236580
0.781	Intermediate Similarity	NPC304445
0.781	Intermediate Similarity	NPC108475
0.781	Intermediate Similarity	NPC170143
0.781	Intermediate Similarity	NPC213947
0.78	Intermediate Similarity	NPC24728
0.78	Intermediate Similarity	NPC190753
0.78	Intermediate Similarity	NPC186148
0.78	Intermediate Similarity	NPC201658
0.78	Intermediate Similarity	NPC118601
0.7788	Intermediate Similarity	NPC170120
0.7778	Intermediate Similarity	NPC124881
0.7768	Intermediate Similarity	NPC475495
0.7767	Intermediate Similarity	NPC212486
0.7757	Intermediate Similarity	NPC474742
0.7757	Intermediate Similarity	NPC476270
0.7755	Intermediate Similarity	NPC128246
0.7745	Intermediate Similarity	NPC65359
0.7745	Intermediate Similarity	NPC206614
0.7745	Intermediate Similarity	NPC474323
0.7736	Intermediate Similarity	NPC474213
0.7723	Intermediate Similarity	NPC58219
0.7723	Intermediate Similarity	NPC53158
0.7723	Intermediate Similarity	NPC471149
0.7723	Intermediate Similarity	NPC224652
0.7723	Intermediate Similarity	NPC177629
0.7706	Intermediate Similarity	NPC100487
0.77	Intermediate Similarity	NPC309757
0.77	Intermediate Similarity	NPC236692
0.7699	Intermediate Similarity	NPC477093
0.7699	Intermediate Similarity	NPC475277
0.7699	Intermediate Similarity	NPC473522
0.7692	Intermediate Similarity	NPC262133
0.7692	Intermediate Similarity	NPC470010
0.7692	Intermediate Similarity	NPC323008
0.7692	Intermediate Similarity	NPC470013
0.7692	Intermediate Similarity	NPC477131
0.7685	Intermediate Similarity	NPC80144
0.7679	Intermediate Similarity	NPC193741
0.7679	Intermediate Similarity	NPC257240
0.7664	Intermediate Similarity	NPC475949
0.7658	Intermediate Similarity	NPC110701
0.7647	Intermediate Similarity	NPC12872
0.7647	Intermediate Similarity	NPC168679
0.7647	Intermediate Similarity	NPC474951
0.7647	Intermediate Similarity	NPC92974
0.7647	Intermediate Similarity	NPC4986
0.7647	Intermediate Similarity	NPC283409
0.7642	Intermediate Similarity	NPC261372
0.7642	Intermediate Similarity	NPC328562
0.7642	Intermediate Similarity	NPC323421
0.7642	Intermediate Similarity	NPC58267
0.7642	Intermediate Similarity	NPC263674
0.7629	Intermediate Similarity	NPC156658
0.7629	Intermediate Similarity	NPC258965
0.7623	Intermediate Similarity	NPC13071
0.7619	Intermediate Similarity	NPC270013
0.7619	Intermediate Similarity	NPC14961
0.7619	Intermediate Similarity	NPC224689
0.7615	Intermediate Similarity	NPC475873
0.76	Intermediate Similarity	NPC47958
0.76	Intermediate Similarity	NPC149725
0.76	Intermediate Similarity	NPC304509
0.7593	Intermediate Similarity	NPC477511
0.7593	Intermediate Similarity	NPC67296
0.7593	Intermediate Similarity	NPC264477
0.7589	Intermediate Similarity	NPC477102
0.7586	Intermediate Similarity	NPC471146
0.7573	Intermediate Similarity	NPC301969
0.7573	Intermediate Similarity	NPC37607
0.7568	Intermediate Similarity	NPC474421
0.7568	Intermediate Similarity	NPC324327
0.7568	Intermediate Similarity	NPC72813
0.7568	Intermediate Similarity	NPC326994
0.7568	Intermediate Similarity	NPC194620
0.7551	Intermediate Similarity	NPC126248
0.7549	Intermediate Similarity	NPC91248

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 NPC44004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	2997
0.2-0.3	3725
0.3-0.4	1398
0.4-0.5	422
0.5-0.6	178
0.6-0.7	31
0.7-0.8	4
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
0.8224	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6371	Approved
0.7647	Intermediate Similarity	NPD1695	Approved
0.6972	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6698	Approved
0.6916	Remote Similarity	NPD46	Approved
0.6829	Remote Similarity	NPD6319	Approved
0.6762	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7492	Approved
0.6694	Remote Similarity	NPD6054	Approved
0.6693	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6641	Remote Similarity	NPD7078	Approved
0.664	Remote Similarity	NPD6015	Approved
0.664	Remote Similarity	NPD6016	Approved
0.6638	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5785	Approved
0.6606	Remote Similarity	NPD7838	Discovery
0.6589	Remote Similarity	NPD7736	Approved
0.6587	Remote Similarity	NPD6370	Approved
0.6587	Remote Similarity	NPD5988	Approved
0.6585	Remote Similarity	NPD7115	Discovery
0.6577	Remote Similarity	NPD5282	Discontinued
0.656	Remote Similarity	NPD6059	Approved
0.6542	Remote Similarity	NPD4249	Approved
0.6538	Remote Similarity	NPD5369	Approved
0.6522	Remote Similarity	NPD5344	Discontinued
0.6522	Remote Similarity	NPD1700	Approved
0.6512	Remote Similarity	NPD8293	Discontinued
0.6481	Remote Similarity	NPD4250	Approved
0.6481	Remote Similarity	NPD4251	Approved
0.6449	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5363	Approved
0.6446	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5362	Discontinued
0.6396	Remote Similarity	NPD7983	Approved
0.6348	Remote Similarity	NPD4225	Approved
0.6341	Remote Similarity	NPD4632	Approved
0.6333	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4270	Approved
0.6321	Remote Similarity	NPD4269	Approved
0.6303	Remote Similarity	NPD6008	Approved
0.6288	Remote Similarity	NPD7319	Approved
0.6261	Remote Similarity	NPD6083	Phase 2
0.6261	Remote Similarity	NPD6084	Phase 2
0.626	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD5697	Approved
0.6241	Remote Similarity	NPD5956	Approved
0.6239	Remote Similarity	NPD5786	Approved
0.623	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.623	Remote Similarity	NPD4634	Approved
0.6228	Remote Similarity	NPD5695	Phase 3
0.621	Remote Similarity	NPD8133	Approved
0.6207	Remote Similarity	NPD5696	Approved
0.6198	Remote Similarity	NPD6881	Approved
0.6198	Remote Similarity	NPD7320	Approved
0.6198	Remote Similarity	NPD6686	Approved
0.6198	Remote Similarity	NPD6899	Approved
0.619	Remote Similarity	NPD6009	Approved
0.6183	Remote Similarity	NPD7507	Approved
0.6179	Remote Similarity	NPD6650	Approved
0.6179	Remote Similarity	NPD6649	Approved
0.6168	Remote Similarity	NPD6435	Approved
0.6167	Remote Similarity	NPD7128	Approved
0.6167	Remote Similarity	NPD6675	Approved
0.6167	Remote Similarity	NPD5739	Approved
0.6167	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD7604	Phase 2
0.6154	Remote Similarity	NPD6648	Approved
0.6148	Remote Similarity	NPD6373	Approved
0.6148	Remote Similarity	NPD6012	Approved
0.6148	Remote Similarity	NPD6372	Approved
0.6148	Remote Similarity	NPD6013	Approved
0.6148	Remote Similarity	NPD6014	Approved
0.6132	Remote Similarity	NPD4822	Approved
0.6132	Remote Similarity	NPD4820	Approved
0.6132	Remote Similarity	NPD4252	Approved
0.6132	Remote Similarity	NPD4819	Approved
0.6132	Remote Similarity	NPD4821	Approved
0.6132	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD5983	Phase 2
0.6116	Remote Similarity	NPD5701	Approved
0.6098	Remote Similarity	NPD7290	Approved
0.6098	Remote Similarity	NPD7102	Approved
0.6098	Remote Similarity	NPD6883	Approved
0.609	Remote Similarity	NPD6033	Approved
0.6066	Remote Similarity	NPD6011	Approved
0.6048	Remote Similarity	NPD6847	Approved
0.6048	Remote Similarity	NPD6617	Approved
0.6048	Remote Similarity	NPD6869	Approved
0.6048	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD8517	Approved
0.6	Remote Similarity	NPD8513	Phase 3
0.5984	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6412	Phase 2
0.5981	Remote Similarity	NPD5368	Approved
0.5971	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5693	Phase 1
0.5963	Remote Similarity	NPD7154	Phase 3
0.5963	Remote Similarity	NPD5331	Approved
0.5963	Remote Similarity	NPD5332	Approved
0.5943	Remote Similarity	NPD4268	Approved
0.5943	Remote Similarity	NPD4271	Approved
0.594	Remote Similarity	NPD6336	Discontinued
0.594	Remote Similarity	NPD8273	Phase 1
0.5932	Remote Similarity	NPD7638	Approved
0.5932	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4790	Discontinued
0.5913	Remote Similarity	NPD5778	Approved
0.5913	Remote Similarity	NPD5779	Approved
0.5891	Remote Similarity	NPD7328	Approved
0.5891	Remote Similarity	NPD7327	Approved
0.5882	Remote Similarity	NPD7640	Approved
0.5882	Remote Similarity	NPD7639	Approved
0.5878	Remote Similarity	NPD8033	Approved
0.5859	Remote Similarity	NPD6274	Approved
0.5846	Remote Similarity	NPD4522	Approved
0.5846	Remote Similarity	NPD7516	Approved
0.5826	Remote Similarity	NPD7637	Suspended
0.5812	Remote Similarity	NPD5210	Approved
0.5812	Remote Similarity	NPD4629	Approved
0.5802	Remote Similarity	NPD8377	Approved
0.5802	Remote Similarity	NPD8294	Approved
0.5794	Remote Similarity	NPD2204	Approved
0.5794	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD4802	Phase 2
0.5794	Remote Similarity	NPD4238	Approved
0.5789	Remote Similarity	NPD4753	Phase 2
0.5789	Remote Similarity	NPD7642	Approved
0.5785	Remote Similarity	NPD5211	Phase 2
0.5778	Remote Similarity	NPD8074	Phase 3
0.5776	Remote Similarity	NPD6399	Phase 3
0.5763	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD8267	Approved
0.5758	Remote Similarity	NPD8378	Approved
0.5758	Remote Similarity	NPD8266	Approved
0.5758	Remote Similarity	NPD8380	Approved
0.5758	Remote Similarity	NPD8296	Approved
0.5758	Remote Similarity	NPD8379	Approved
0.5758	Remote Similarity	NPD7503	Approved
0.5758	Remote Similarity	NPD8335	Approved
0.5758	Remote Similarity	NPD6921	Approved
0.5758	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD8268	Approved
0.5758	Remote Similarity	NPD8269	Approved
0.575	Remote Similarity	NPD5285	Approved
0.575	Remote Similarity	NPD4696	Approved
0.575	Remote Similarity	NPD5286	Approved
0.5727	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD7101	Approved
0.5725	Remote Similarity	NPD7100	Approved
0.5714	Remote Similarity	NPD4755	Approved
0.5692	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD6317	Approved
0.5691	Remote Similarity	NPD5141	Approved
0.569	Remote Similarity	NPD8034	Phase 2
0.569	Remote Similarity	NPD8035	Phase 2
0.5683	Remote Similarity	NPD6845	Suspended
0.5678	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD4788	Approved
0.5672	Remote Similarity	NPD8328	Phase 3
0.5672	Remote Similarity	NPD7829	Approved
0.5672	Remote Similarity	NPD7830	Approved
0.5656	Remote Similarity	NPD4633	Approved
0.5656	Remote Similarity	NPD5226	Approved
0.5656	Remote Similarity	NPD5224	Approved
0.5656	Remote Similarity	NPD5225	Approved
0.5652	Remote Similarity	NPD6673	Approved
0.5652	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6080	Approved
0.5652	Remote Similarity	NPD6101	Approved
0.5652	Remote Similarity	NPD6904	Approved
0.5649	Remote Similarity	NPD6314	Approved
0.5649	Remote Similarity	NPD6335	Approved
0.5649	Remote Similarity	NPD6313	Approved
0.5648	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.562	Remote Similarity	NPD4700	Approved
0.5614	Remote Similarity	NPD7524	Approved
0.5612	Remote Similarity	NPD7260	Phase 2
0.561	Remote Similarity	NPD5175	Approved
0.561	Remote Similarity	NPD5174	Approved
0.5603	Remote Similarity	NPD5692	Phase 3

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