NPASS Compound

Structure

NPC165383 OpenBabel07101718182D 26 28 0 0 1 0 0 0 0 0999 V2000 -4.1369 4.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1082 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8279 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6470 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0592 2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0592 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1369 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6470 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0880 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0592 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8970 -0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0880 1.3090 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 13 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 9 10 2 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 20 1 1 0 0 0 13 26 1 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 12 1 1 0 0 0 15 17 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 25 1 6 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 5 1 6 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.16
Volume:	365.729
LogP:	2.219
LogD:	1.118
LogS:	-3.071
# Rotatable Bonds:	3
TPSA:	82.2
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	5.43
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.618
MDCK Permeability:	5.317190880305134e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.465

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.868
Plasma Protein Binding (PPB):	82.60967254638672%
Volume Distribution (VD):	1.345
Pgp-substrate:	19.461044311523438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.374
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.33
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.677
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	13.432
Half-life (T1/2):	0.129

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.583
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.205
Rat Oral Acute Toxicity:	0.686
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.773
Carcinogencity:	0.288
Eye Corrosion:	0.99
Eye Irritation:	0.273
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC165383

Natural Product ID:	NPC165383
*Common Name:**	8Alpha-(2's,3's-Epoxy-2'-Methylbutyryloxy)-9-Oxo-Germacra-4E,1(10)E-Dien-6Beta,12-Olide
IUPAC Name:	[(3aS,4R,6Z,10E,11aS)-6,10-dimethyl-3-methylidene-2,5-dioxo-4,8,9,11a-tetrahydro-3aH-cyclodeca[b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate
Synonyms:
Standard InCHIKey:	QZRJGJCGCXCSOM-ZEKXQJKRSA-N
Standard InCHI:	InChI=1S/C20H24O6/c1-10-7-6-8-11(2)16(21)17(25-19(23)20(5)13(4)26-20)15-12(3)18(22)24-14(15)9-10/h8-9,13-15,17H,3,6-7H2,1-2,4-5H3/b10-9+,11-8-/t13-,14-,15-,17+,20-/m0/s1
SMILES:	C/C/1=C[C@@H]2OC(=O)C(=C)[C@@H]2[C@H](C(=O)/C(=CCC1)/C)OC(=O)[C@@]1(C)O[C@H]1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL205200
PubChem CID:	21577297
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:0001771] Germacranolides 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
NPO12991	Montanoa hibiscifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104492]
NPO12991	Montanoa hibiscifolia	Species	Asteraceae	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
Others	3

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	50.0	uM	PMID[500186]
NPT2	Others	Unspecified		Activity	=	50.0	uM	PMID[500187]
NPT2	Others	Unspecified		Activity	=	20.0	uM	PMID[500187]

☑ 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 NPC165383 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	247
0.1-0.2	1848
0.2-0.3	7195
0.3-0.4	14397
0.4-0.5	11063
0.5-0.6	5338
0.6-0.7	2011
0.7-0.8	520
0.8-0.85	67
0.85-0.9	6
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9419	High Similarity	NPC266957
0.9022	High Similarity	NPC17585
0.8737	High Similarity	NPC477512
0.8667	High Similarity	NPC475902
0.8646	High Similarity	NPC264477
0.8646	High Similarity	NPC477511
0.8646	High Similarity	NPC164598
0.8646	High Similarity	NPC474339
0.8542	High Similarity	NPC475949
0.8526	High Similarity	NPC471140
0.8495	Intermediate Similarity	NPC475302
0.8488	Intermediate Similarity	NPC270126
0.8478	Intermediate Similarity	NPC49342
0.8478	Intermediate Similarity	NPC251385
0.8444	Intermediate Similarity	NPC279859
0.8444	Intermediate Similarity	NPC38576
0.8421	Intermediate Similarity	NPC476275
0.8404	Intermediate Similarity	NPC471147
0.8387	Intermediate Similarity	NPC20713
0.8384	Intermediate Similarity	NPC471143
0.8384	Intermediate Similarity	NPC477510
0.8316	Intermediate Similarity	NPC475659
0.828	Intermediate Similarity	NPC329857
0.828	Intermediate Similarity	NPC469718
0.8265	Intermediate Similarity	NPC201718
0.8265	Intermediate Similarity	NPC476270
0.8261	Intermediate Similarity	NPC287089
0.8256	Intermediate Similarity	NPC171204
0.8256	Intermediate Similarity	NPC141789
0.8256	Intermediate Similarity	NPC476028
0.8247	Intermediate Similarity	NPC471144
0.8229	Intermediate Similarity	NPC473859
0.8218	Intermediate Similarity	NPC477513
0.8211	Intermediate Similarity	NPC473330
0.8211	Intermediate Similarity	NPC140543
0.8211	Intermediate Similarity	NPC473316
0.8182	Intermediate Similarity	NPC149371
0.8182	Intermediate Similarity	NPC281132
0.8182	Intermediate Similarity	NPC471148
0.8172	Intermediate Similarity	NPC151770
0.8172	Intermediate Similarity	NPC166919
0.8163	Intermediate Similarity	NPC288876
0.8132	Intermediate Similarity	NPC470755
0.8125	Intermediate Similarity	NPC474947
0.8111	Intermediate Similarity	NPC474703
0.809	Intermediate Similarity	NPC141810
0.8081	Intermediate Similarity	NPC46998
0.8081	Intermediate Similarity	NPC110443
0.8081	Intermediate Similarity	NPC47880
0.8081	Intermediate Similarity	NPC128733
0.8081	Intermediate Similarity	NPC133907
0.8081	Intermediate Similarity	NPC185141
0.8065	Intermediate Similarity	NPC469628
0.8065	Intermediate Similarity	NPC471047
0.8065	Intermediate Similarity	NPC469631
0.8065	Intermediate Similarity	NPC469653
0.8065	Intermediate Similarity	NPC475906
0.8061	Intermediate Similarity	NPC208233
0.8061	Intermediate Similarity	NPC54843
0.8043	Intermediate Similarity	NPC469910
0.8043	Intermediate Similarity	NPC50637
0.8041	Intermediate Similarity	NPC35498
0.8022	Intermediate Similarity	NPC158756
0.8021	Intermediate Similarity	NPC121825
0.8021	Intermediate Similarity	NPC476267
0.802	Intermediate Similarity	NPC474741
0.802	Intermediate Similarity	NPC472756
0.8	Intermediate Similarity	NPC475690
0.8	Intermediate Similarity	NPC173609
0.7957	Intermediate Similarity	NPC471739
0.7957	Intermediate Similarity	NPC231889
0.7938	Intermediate Similarity	NPC477922
0.7938	Intermediate Similarity	NPC471142
0.7935	Intermediate Similarity	NPC319795
0.7935	Intermediate Similarity	NPC50362
0.7935	Intermediate Similarity	NPC38468
0.7917	Intermediate Similarity	NPC295204
0.7917	Intermediate Similarity	NPC469692
0.7917	Intermediate Similarity	NPC288240
0.7917	Intermediate Similarity	NPC162205
0.7917	Intermediate Similarity	NPC469645
0.7917	Intermediate Similarity	NPC273579
0.7912	Intermediate Similarity	NPC40746
0.7912	Intermediate Similarity	NPC169575
0.7912	Intermediate Similarity	NPC475947
0.7907	Intermediate Similarity	NPC476355
0.79	Intermediate Similarity	NPC15993
0.7895	Intermediate Similarity	NPC473619
0.7895	Intermediate Similarity	NPC474232
0.7895	Intermediate Similarity	NPC475748
0.7889	Intermediate Similarity	NPC286229
0.7872	Intermediate Similarity	NPC475819
0.7872	Intermediate Similarity	NPC476805
0.7872	Intermediate Similarity	NPC476803
0.7865	Intermediate Similarity	NPC473981
0.7865	Intermediate Similarity	NPC473980
0.7865	Intermediate Similarity	NPC617
0.7857	Intermediate Similarity	NPC230800
0.7857	Intermediate Similarity	NPC279621
0.7857	Intermediate Similarity	NPC477921
0.7841	Intermediate Similarity	NPC97516
0.7841	Intermediate Similarity	NPC474760
0.7835	Intermediate Similarity	NPC57405
0.7835	Intermediate Similarity	NPC303942
0.7822	Intermediate Similarity	NPC320019
0.7822	Intermediate Similarity	NPC324017
0.7812	Intermediate Similarity	NPC473321
0.7791	Intermediate Similarity	NPC269206
0.7791	Intermediate Similarity	NPC58956
0.7791	Intermediate Similarity	NPC295633
0.7789	Intermediate Similarity	NPC475971
0.7753	Intermediate Similarity	NPC475699
0.7745	Intermediate Similarity	NPC475871
0.7745	Intermediate Similarity	NPC472755
0.7745	Intermediate Similarity	NPC475945
0.7745	Intermediate Similarity	NPC19239
0.7745	Intermediate Similarity	NPC474166
0.7745	Intermediate Similarity	NPC475873
0.7732	Intermediate Similarity	NPC125674
0.7732	Intermediate Similarity	NPC475838
0.7732	Intermediate Similarity	NPC228451
0.7727	Intermediate Similarity	NPC123360
0.7723	Intermediate Similarity	NPC472753
0.7723	Intermediate Similarity	NPC474742
0.7717	Intermediate Similarity	NPC59097
0.7717	Intermediate Similarity	NPC131669
0.7717	Intermediate Similarity	NPC473390
0.7708	Intermediate Similarity	NPC179394
0.7708	Intermediate Similarity	NPC144133
0.7708	Intermediate Similarity	NPC51653
0.7708	Intermediate Similarity	NPC312042
0.7701	Intermediate Similarity	NPC140287
0.77	Intermediate Similarity	NPC279561
0.77	Intermediate Similarity	NPC473326
0.7692	Intermediate Similarity	NPC281949
0.7692	Intermediate Similarity	NPC25684
0.7692	Intermediate Similarity	NPC301477
0.7692	Intermediate Similarity	NPC474716
0.7692	Intermediate Similarity	NPC24417
0.7674	Intermediate Similarity	NPC163003
0.7667	Intermediate Similarity	NPC98557
0.7667	Intermediate Similarity	NPC178277
0.7667	Intermediate Similarity	NPC471740
0.7667	Intermediate Similarity	NPC167881
0.766	Intermediate Similarity	NPC475461
0.766	Intermediate Similarity	NPC305475
0.766	Intermediate Similarity	NPC469483
0.7653	Intermediate Similarity	NPC469632
0.7653	Intermediate Similarity	NPC474247
0.7647	Intermediate Similarity	NPC472754
0.7647	Intermediate Similarity	NPC474747
0.7634	Intermediate Similarity	NPC96259
0.7634	Intermediate Similarity	NPC141193
0.7634	Intermediate Similarity	NPC476804
0.7624	Intermediate Similarity	NPC469551
0.7614	Intermediate Similarity	NPC155587
0.7609	Intermediate Similarity	NPC471326
0.7609	Intermediate Similarity	NPC221231
0.7609	Intermediate Similarity	NPC229825
0.7609	Intermediate Similarity	NPC85772
0.7596	Intermediate Similarity	NPC16313
0.7596	Intermediate Similarity	NPC9303
0.7596	Intermediate Similarity	NPC475802
0.7582	Intermediate Similarity	NPC223904
0.7579	Intermediate Similarity	NPC471738
0.7579	Intermediate Similarity	NPC72513
0.7579	Intermediate Similarity	NPC475703
0.7576	Intermediate Similarity	NPC14961
0.7576	Intermediate Similarity	NPC474490
0.7576	Intermediate Similarity	NPC471141
0.7576	Intermediate Similarity	NPC270013
0.757	Intermediate Similarity	NPC475495
0.7556	Intermediate Similarity	NPC93763
0.7556	Intermediate Similarity	NPC108816
0.7553	Intermediate Similarity	NPC255307
0.7551	Intermediate Similarity	NPC212486
0.7547	Intermediate Similarity	NPC38154
0.7528	Intermediate Similarity	NPC235906
0.7527	Intermediate Similarity	NPC318468
0.7527	Intermediate Similarity	NPC128429
0.7527	Intermediate Similarity	NPC475989
0.7527	Intermediate Similarity	NPC272814
0.7526	Intermediate Similarity	NPC62815
0.7526	Intermediate Similarity	NPC471818
0.7526	Intermediate Similarity	NPC475855
0.7524	Intermediate Similarity	NPC72813
0.7524	Intermediate Similarity	NPC475510
0.7524	Intermediate Similarity	NPC194620
0.7524	Intermediate Similarity	NPC474421
0.7524	Intermediate Similarity	NPC324327
0.7524	Intermediate Similarity	NPC475587
0.7524	Intermediate Similarity	NPC326994
0.75	Intermediate Similarity	NPC473522
0.75	Intermediate Similarity	NPC476315
0.75	Intermediate Similarity	NPC473715
0.75	Intermediate Similarity	NPC477093
0.75	Intermediate Similarity	NPC471325
0.75	Intermediate Similarity	NPC172998
0.75	Intermediate Similarity	NPC31645
0.75	Intermediate Similarity	NPC301596

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 NPC165383 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	2433
0.2-0.3	3971
0.3-0.4	1741
0.4-0.5	548
0.5-0.6	199
0.6-0.7	24
0.7-0.8	3
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
0.7935	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6698	Approved
0.7	Intermediate Similarity	NPD46	Approved
0.69	Remote Similarity	NPD1695	Approved
0.6875	Remote Similarity	NPD5209	Approved
0.6847	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD5785	Approved
0.6591	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4225	Approved
0.6505	Remote Similarity	NPD7838	Discovery
0.65	Remote Similarity	NPD5363	Approved
0.65	Remote Similarity	NPD1694	Approved
0.6496	Remote Similarity	NPD7115	Discovery
0.6476	Remote Similarity	NPD5282	Discontinued
0.6442	Remote Similarity	NPD7983	Approved
0.6364	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5786	Approved
0.6263	Remote Similarity	NPD5369	Approved
0.6239	Remote Similarity	NPD5696	Approved
0.6207	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD2204	Approved
0.62	Remote Similarity	NPD4269	Approved
0.62	Remote Similarity	NPD4270	Approved
0.6186	Remote Similarity	NPD4756	Discovery
0.6162	Remote Similarity	NPD4252	Approved
0.6139	Remote Similarity	NPD7154	Phase 3
0.6132	Remote Similarity	NPD5693	Phase 1
0.6121	Remote Similarity	NPD2067	Discontinued
0.6091	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6008	Approved
0.6048	Remote Similarity	NPD7642	Approved
0.604	Remote Similarity	NPD6435	Approved
0.6036	Remote Similarity	NPD6648	Approved
0.6017	Remote Similarity	NPD8297	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5697	Approved
0.5985	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5344	Discontinued
0.598	Remote Similarity	NPD6110	Phase 1
0.5963	Remote Similarity	NPD5695	Phase 3
0.5948	Remote Similarity	NPD6686	Approved
0.5948	Remote Similarity	NPD6899	Approved
0.5948	Remote Similarity	NPD6881	Approved
0.5935	Remote Similarity	NPD6319	Approved
0.5932	Remote Similarity	NPD6649	Approved
0.5932	Remote Similarity	NPD6650	Approved
0.5926	Remote Similarity	NPD5778	Approved
0.5926	Remote Similarity	NPD5779	Approved
0.5913	Remote Similarity	NPD5739	Approved
0.5913	Remote Similarity	NPD6402	Approved
0.5913	Remote Similarity	NPD6675	Approved
0.5913	Remote Similarity	NPD7128	Approved
0.5897	Remote Similarity	NPD6373	Approved
0.5897	Remote Similarity	NPD6013	Approved
0.5897	Remote Similarity	NPD6012	Approved
0.5897	Remote Similarity	NPD6014	Approved
0.5897	Remote Similarity	NPD6372	Approved
0.5887	Remote Similarity	NPD8517	Approved
0.5887	Remote Similarity	NPD8515	Approved
0.5887	Remote Similarity	NPD8516	Approved
0.5887	Remote Similarity	NPD8513	Phase 3
0.5882	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7492	Approved
0.5865	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5701	Approved
0.5856	Remote Similarity	NPD6084	Phase 2
0.5856	Remote Similarity	NPD6083	Phase 2
0.5847	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6883	Approved
0.5847	Remote Similarity	NPD7102	Approved
0.5847	Remote Similarity	NPD7290	Approved
0.5846	Remote Similarity	NPD7260	Phase 2
0.5842	Remote Similarity	NPD4820	Approved
0.5842	Remote Similarity	NPD4819	Approved
0.5842	Remote Similarity	NPD4821	Approved
0.5842	Remote Similarity	NPD5368	Approved
0.5842	Remote Similarity	NPD4822	Approved
0.5827	Remote Similarity	NPD6616	Approved
0.5825	Remote Similarity	NPD5362	Discontinued
0.5816	Remote Similarity	NPD8039	Approved
0.5812	Remote Similarity	NPD7320	Approved
0.5812	Remote Similarity	NPD6011	Approved
0.581	Remote Similarity	NPD4249	Approved
0.5806	Remote Similarity	NPD6054	Approved
0.5806	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4271	Approved
0.58	Remote Similarity	NPD4268	Approved
0.5798	Remote Similarity	NPD6869	Approved
0.5798	Remote Similarity	NPD8130	Phase 1
0.5798	Remote Similarity	NPD6847	Approved
0.5798	Remote Similarity	NPD6617	Approved
0.5794	Remote Similarity	NPD6080	Approved
0.5794	Remote Similarity	NPD6673	Approved
0.5794	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6101	Approved
0.5794	Remote Similarity	NPD6904	Approved
0.5794	Remote Similarity	NPD7829	Approved
0.5794	Remote Similarity	NPD5370	Suspended
0.5794	Remote Similarity	NPD7830	Approved
0.5781	Remote Similarity	NPD7078	Approved
0.5766	Remote Similarity	NPD7839	Suspended
0.5763	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.576	Remote Similarity	NPD6016	Approved
0.576	Remote Similarity	NPD6015	Approved
0.5755	Remote Similarity	NPD4250	Approved
0.5755	Remote Similarity	NPD4251	Approved
0.575	Remote Similarity	NPD6882	Approved
0.575	Remote Similarity	NPD6053	Discontinued
0.5741	Remote Similarity	NPD5692	Phase 3
0.5736	Remote Similarity	NPD7736	Approved
0.5714	Remote Similarity	NPD5988	Approved
0.5714	Remote Similarity	NPD6370	Approved
0.5688	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD5694	Approved
0.5688	Remote Similarity	NPD6411	Approved
0.5688	Remote Similarity	NPD6050	Approved
0.5682	Remote Similarity	NPD6845	Suspended
0.568	Remote Similarity	NPD6059	Approved
0.5678	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD5210	Approved
0.5676	Remote Similarity	NPD4629	Approved
0.5676	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5330	Approved
0.566	Remote Similarity	NPD7521	Approved
0.566	Remote Similarity	NPD7146	Approved
0.566	Remote Similarity	NPD7334	Approved
0.566	Remote Similarity	NPD6684	Approved
0.566	Remote Similarity	NPD6409	Approved
0.5659	Remote Similarity	NPD8074	Phase 3
0.5659	Remote Similarity	NPD8293	Discontinued
0.5644	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6399	Phase 3
0.5635	Remote Similarity	NPD8444	Approved
0.561	Remote Similarity	NPD6274	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