NPASS Compound

Structure

NPC470755 OpenBabel07101719132D 26 27 0 0 1 0 0 0 0 0999 V2000 2.8116 1.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3321 -3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8765 -1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4697 -0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6685 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1646 -4.3991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9077 -5.0682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9309 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0056 -5.6862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 0.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9254 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2135 -4.7081 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 1.0649 -2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -4.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8588 -4.7592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9454 -5.9953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 -4.3480 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 0.3217 -3.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 12 1 0 0 0 0 6 13 2 0 0 0 0 7 8 1 0 0 0 0 7 15 2 0 0 0 0 8 21 1 0 0 0 0 9 12 2 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 9 1 6 0 0 0 16 18 1 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 1 0 0 0 18 14 1 1 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	374.286
LogP:	0.34
LogD:	1.135
LogS:	-2.926
# Rotatable Bonds:	6
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.349
Synthetic Accessibility Score:	4.936
Fsp3:	0.55
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:	-4.764
MDCK Permeability:	5.808625428471714e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.908
20% Bioavailability (F20%):	0.554
30% Bioavailability (F30%):	0.593

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.253
Plasma Protein Binding (PPB):	72.33094024658203%
Volume Distribution (VD):	0.926
Pgp-substrate:	23.945764541625977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.069
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.136
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.17
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.451
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	5.623
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.285
Drug-inuced Liver Injury (DILI):	0.118
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.346
Maximum Recommended Daily Dose:	0.232
Skin Sensitization:	0.902
Carcinogencity:	0.105
Eye Corrosion:	0.013
Eye Irritation:	0.023
Respiratory Toxicity:	0.607

Download Data

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

Natural Product: NPC470755

Natural Product ID:	NPC470755
*Common Name:**	Eupatoriopicrin
IUPAC Name:	[(3aR,4R,6Z,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate
Synonyms:	Eupatoriopicrin; Eupatoriopicrine
Standard InCHIKey:	VWJYWGYJIDQUEG-UWRPYMCXSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-12-5-4-6-13(2)10-17(26-20(24)15(11-22)7-8-21)18-14(3)19(23)25-16(18)9-12/h6-7,9,16-18,21-22H,3-5,8,10-11H2,1-2H3/b12-9+,13-6-,15-7+/t16-,17-,18+/m1/s1
SMILES:	OC/C=C(/C(=O)O[C@@H]1C/C(=CCC/C(=C/[C@@H]2[C@@H]1C(=C)C(=O)O2)/C)/C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL221283
PubChem CID:	6917047
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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]

☑ 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
ED50	1
IC50	3
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2716	Individual Protein	UDP-N-acetylglucosamine 1-carboxyvinyltransferase	Escherichia coli K-12	IC50	=	32700.0	nM	PMID[524223]
NPT2717	Individual Protein	UDP-N-acetylglucosamine 1-carboxyvinyltransferase	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)	IC50	=	19800.0	nM	PMID[524223]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.3	umol/L	PMID[524224]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5700.0	nM	PMID[524225]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC80	=	13.4	uM	PMID[524225]

☑ 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 NPC470755 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	171
0.1-0.2	1197
0.2-0.3	5083
0.3-0.4	11642
0.4-0.5	13358
0.5-0.6	6649
0.6-0.7	3411
0.7-0.8	973
0.8-0.85	97
0.85-0.9	52
0.9-0.95	37
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC158756
0.9747	High Similarity	NPC169575
0.9747	High Similarity	NPC40746
0.9634	High Similarity	NPC475819
0.9634	High Similarity	NPC476805
0.963	High Similarity	NPC469910
0.95	High Similarity	NPC473390
0.95	High Similarity	NPC131669
0.9494	High Similarity	NPC24417
0.9398	High Similarity	NPC476803
0.939	High Similarity	NPC475461
0.939	High Similarity	NPC305475
0.9383	High Similarity	NPC476804
0.9375	High Similarity	NPC229825
0.9268	High Similarity	NPC255307
0.9259	High Similarity	NPC59097
0.9241	High Similarity	NPC167881
0.9241	High Similarity	NPC98557
0.9176	High Similarity	NPC474232
0.9146	High Similarity	NPC141193
0.9146	High Similarity	NPC96259
0.9146	High Similarity	NPC191476
0.9146	High Similarity	NPC114979
0.9114	High Similarity	NPC93763
0.9114	High Similarity	NPC196653
0.9114	High Similarity	NPC108816
0.9114	High Similarity	NPC471465
0.9024	High Similarity	NPC116543
0.9012	High Similarity	NPC52861
0.9	High Similarity	NPC270126
0.8987	High Similarity	NPC116177
0.8987	High Similarity	NPC320630
0.8987	High Similarity	NPC171204
0.8987	High Similarity	NPC7563
0.8987	High Similarity	NPC141789
0.8987	High Similarity	NPC476028
0.8977	High Similarity	NPC477922
0.8977	High Similarity	NPC471142
0.8953	High Similarity	NPC475855
0.8929	High Similarity	NPC150755
0.8889	High Similarity	NPC281132
0.8876	High Similarity	NPC230800
0.8876	High Similarity	NPC477921
0.8861	High Similarity	NPC68819
0.8851	High Similarity	NPC473321
0.875	High Similarity	NPC125674
0.875	High Similarity	NPC162205
0.875	High Similarity	NPC273579
0.875	High Similarity	NPC475838
0.875	High Similarity	NPC295204
0.875	High Similarity	NPC228451
0.875	High Similarity	NPC475302
0.875	High Similarity	NPC288240
0.8736	High Similarity	NPC469368
0.8736	High Similarity	NPC144133
0.8736	High Similarity	NPC179394
0.8736	High Similarity	NPC473619
0.8721	High Similarity	NPC473715
0.8652	High Similarity	NPC474247
0.8642	High Similarity	NPC267231
0.8608	High Similarity	NPC476355
0.8588	High Similarity	NPC261380
0.8588	High Similarity	NPC165162
0.8587	High Similarity	NPC288876
0.8539	High Similarity	NPC469645
0.8539	High Similarity	NPC469692
0.8519	High Similarity	NPC97516
0.8519	High Similarity	NPC474760
0.8488	Intermediate Similarity	NPC469483
0.8481	Intermediate Similarity	NPC58956
0.8481	Intermediate Similarity	NPC295633
0.8481	Intermediate Similarity	NPC269206
0.8478	Intermediate Similarity	NPC471144
0.8462	Intermediate Similarity	NPC473859
0.8462	Intermediate Similarity	NPC279621
0.8452	Intermediate Similarity	NPC85772
0.8444	Intermediate Similarity	NPC121825
0.8409	Intermediate Similarity	NPC474032
0.8395	Intermediate Similarity	NPC123360
0.8391	Intermediate Similarity	NPC266957
0.8375	Intermediate Similarity	NPC114727
0.8375	Intermediate Similarity	NPC48641
0.8375	Intermediate Similarity	NPC140287
0.8375	Intermediate Similarity	NPC476590
0.8372	Intermediate Similarity	NPC21469
0.8354	Intermediate Similarity	NPC163003
0.8352	Intermediate Similarity	NPC475659
0.8315	Intermediate Similarity	NPC129419
0.8313	Intermediate Similarity	NPC19841
0.8313	Intermediate Similarity	NPC89128
0.8295	Intermediate Similarity	NPC287089
0.828	Intermediate Similarity	NPC141191
0.8276	Intermediate Similarity	NPC261721
0.8242	Intermediate Similarity	NPC57405
0.8242	Intermediate Similarity	NPC303942
0.8235	Intermediate Similarity	NPC89555
0.8222	Intermediate Similarity	NPC111114
0.8222	Intermediate Similarity	NPC300312
0.8222	Intermediate Similarity	NPC261607
0.8202	Intermediate Similarity	NPC206001
0.8202	Intermediate Similarity	NPC218927
0.8202	Intermediate Similarity	NPC268298
0.8202	Intermediate Similarity	NPC295312
0.8191	Intermediate Similarity	NPC475949
0.8182	Intermediate Similarity	NPC160138
0.8182	Intermediate Similarity	NPC72513
0.8172	Intermediate Similarity	NPC169205
0.8172	Intermediate Similarity	NPC471462
0.8171	Intermediate Similarity	NPC235906
0.8152	Intermediate Similarity	NPC304886
0.8152	Intermediate Similarity	NPC471141
0.814	Intermediate Similarity	NPC250315
0.814	Intermediate Similarity	NPC475947
0.8132	Intermediate Similarity	NPC475912
0.8132	Intermediate Similarity	NPC165383
0.8118	Intermediate Similarity	NPC325031
0.8118	Intermediate Similarity	NPC141810
0.8118	Intermediate Similarity	NPC301477
0.8118	Intermediate Similarity	NPC281949
0.8118	Intermediate Similarity	NPC25684
0.8111	Intermediate Similarity	NPC71533
0.8111	Intermediate Similarity	NPC106510
0.8105	Intermediate Similarity	NPC474339
0.8105	Intermediate Similarity	NPC46998
0.8105	Intermediate Similarity	NPC133907
0.8105	Intermediate Similarity	NPC164598
0.8105	Intermediate Similarity	NPC185141
0.8105	Intermediate Similarity	NPC110443
0.8105	Intermediate Similarity	NPC128733
0.8095	Intermediate Similarity	NPC470244
0.8095	Intermediate Similarity	NPC470239
0.8095	Intermediate Similarity	NPC178277
0.809	Intermediate Similarity	NPC260343
0.809	Intermediate Similarity	NPC477302
0.809	Intermediate Similarity	NPC136879
0.8068	Intermediate Similarity	NPC50637
0.8065	Intermediate Similarity	NPC306041
0.8065	Intermediate Similarity	NPC185553
0.8049	Intermediate Similarity	NPC155587
0.8043	Intermediate Similarity	NPC474338
0.8043	Intermediate Similarity	NPC140543
0.8043	Intermediate Similarity	NPC469632
0.8043	Intermediate Similarity	NPC167219
0.8023	Intermediate Similarity	NPC310450
0.8023	Intermediate Similarity	NPC475046
0.8023	Intermediate Similarity	NPC474959
0.8023	Intermediate Similarity	NPC474252
0.8023	Intermediate Similarity	NPC11383
0.8021	Intermediate Similarity	NPC149371
0.8021	Intermediate Similarity	NPC471148
0.8	Intermediate Similarity	NPC67183
0.8	Intermediate Similarity	NPC166919
0.7957	Intermediate Similarity	NPC48803
0.7957	Intermediate Similarity	NPC36954
0.7957	Intermediate Similarity	NPC275960
0.7957	Intermediate Similarity	NPC193645
0.7957	Intermediate Similarity	NPC90121
0.7957	Intermediate Similarity	NPC14961
0.7957	Intermediate Similarity	NPC270013
0.7955	Intermediate Similarity	NPC125290
0.7931	Intermediate Similarity	NPC284472
0.7931	Intermediate Similarity	NPC286770
0.7931	Intermediate Similarity	NPC474703
0.7931	Intermediate Similarity	NPC229799
0.7931	Intermediate Similarity	NPC318468
0.7917	Intermediate Similarity	NPC469657
0.7917	Intermediate Similarity	NPC47880
0.7917	Intermediate Similarity	NPC244456
0.7912	Intermediate Similarity	NPC473455
0.7912	Intermediate Similarity	NPC473448
0.7907	Intermediate Similarity	NPC471325
0.7907	Intermediate Similarity	NPC470241
0.7901	Intermediate Similarity	NPC129665
0.7895	Intermediate Similarity	NPC187268
0.7895	Intermediate Similarity	NPC473326
0.7889	Intermediate Similarity	NPC202672
0.7882	Intermediate Similarity	NPC99651
0.7882	Intermediate Similarity	NPC617
0.7882	Intermediate Similarity	NPC475210
0.7879	Intermediate Similarity	NPC477513
0.7875	Intermediate Similarity	NPC476591
0.7875	Intermediate Similarity	NPC88877
0.7872	Intermediate Similarity	NPC17585
0.7872	Intermediate Similarity	NPC476315
0.7865	Intermediate Similarity	NPC315395
0.7865	Intermediate Similarity	NPC107787
0.7865	Intermediate Similarity	NPC316426
0.7857	Intermediate Similarity	NPC100487
0.7857	Intermediate Similarity	NPC187568
0.7857	Intermediate Similarity	NPC470240
0.7857	Intermediate Similarity	NPC476794
0.7857	Intermediate Similarity	NPC57744
0.7857	Intermediate Similarity	NPC41780
0.7849	Intermediate Similarity	NPC477131
0.7849	Intermediate Similarity	NPC81386
0.7849	Intermediate Similarity	NPC471147
0.7849	Intermediate Similarity	NPC476267
0.7849	Intermediate Similarity	NPC474035
0.7848	Intermediate Similarity	NPC194871
0.7841	Intermediate Similarity	NPC82297

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 NPC470755 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1770
0.2-0.3	3770
0.3-0.4	2338
0.4-0.5	706
0.5-0.6	334
0.6-0.7	46
0.7-0.8	22
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7957	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD5785	Approved
0.7753	Intermediate Similarity	NPD5363	Approved
0.7528	Intermediate Similarity	NPD7154	Phase 3
0.7527	Intermediate Similarity	NPD6698	Approved
0.7527	Intermediate Similarity	NPD46	Approved
0.7526	Intermediate Similarity	NPD4225	Approved
0.7416	Intermediate Similarity	NPD4269	Approved
0.7416	Intermediate Similarity	NPD4270	Approved
0.7386	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4252	Approved
0.7363	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6371	Approved
0.7283	Intermediate Similarity	NPD5786	Approved
0.7263	Intermediate Similarity	NPD7983	Approved
0.7159	Intermediate Similarity	NPD4268	Approved
0.7159	Intermediate Similarity	NPD4271	Approved
0.7143	Intermediate Similarity	NPD5362	Discontinued
0.7111	Intermediate Similarity	NPD5369	Approved
0.7097	Intermediate Similarity	NPD4249	Approved
0.7033	Intermediate Similarity	NPD5209	Approved
0.7021	Intermediate Similarity	NPD4251	Approved
0.7021	Intermediate Similarity	NPD4250	Approved
0.701	Intermediate Similarity	NPD5778	Approved
0.701	Intermediate Similarity	NPD5779	Approved
0.7	Intermediate Similarity	NPD4821	Approved
0.7	Intermediate Similarity	NPD4822	Approved
0.7	Intermediate Similarity	NPD4819	Approved
0.7	Intermediate Similarity	NPD4820	Approved
0.6989	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7838	Discovery
0.6875	Remote Similarity	NPD1695	Approved
0.6875	Remote Similarity	NPD5370	Suspended
0.6848	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6435	Approved
0.6832	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1694	Approved
0.68	Remote Similarity	NPD7839	Suspended
0.6778	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5282	Discontinued
0.6757	Remote Similarity	NPD7115	Discovery
0.6735	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD4756	Discovery
0.6636	Remote Similarity	NPD6686	Approved
0.663	Remote Similarity	NPD5368	Approved
0.6606	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5332	Approved
0.6596	Remote Similarity	NPD5331	Approved
0.6566	Remote Similarity	NPD7637	Suspended
0.6566	Remote Similarity	NPD6411	Approved
0.6559	Remote Similarity	NPD4790	Discontinued
0.6548	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7640	Approved
0.6442	Remote Similarity	NPD7639	Approved
0.6396	Remote Similarity	NPD6053	Discontinued
0.6381	Remote Similarity	NPD5344	Discontinued
0.6379	Remote Similarity	NPD8513	Phase 3
0.6379	Remote Similarity	NPD8517	Approved
0.6379	Remote Similarity	NPD8515	Approved
0.6379	Remote Similarity	NPD8516	Approved
0.6346	Remote Similarity	NPD7638	Approved
0.6337	Remote Similarity	NPD6399	Phase 3
0.6265	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8039	Approved
0.6207	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6648	Approved
0.6116	Remote Similarity	NPD8074	Phase 3
0.6111	Remote Similarity	NPD6647	Phase 2
0.6095	Remote Similarity	NPD6084	Phase 2
0.6095	Remote Similarity	NPD7902	Approved
0.6095	Remote Similarity	NPD6083	Phase 2
0.6091	Remote Similarity	NPD5697	Approved
0.6082	Remote Similarity	NPD6110	Phase 1
0.6061	Remote Similarity	NPD6422	Discontinued
0.6058	Remote Similarity	NPD5695	Phase 3
0.6047	Remote Similarity	NPD3197	Phase 1
0.6038	Remote Similarity	NPD5696	Approved
0.6036	Remote Similarity	NPD6899	Approved
0.6036	Remote Similarity	NPD6881	Approved
0.6018	Remote Similarity	NPD6650	Approved
0.6018	Remote Similarity	NPD2204	Approved
0.6018	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD4228	Discovery
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD7830	Approved
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD7642	Approved
0.5982	Remote Similarity	NPD6014	Approved
0.5982	Remote Similarity	NPD6372	Approved
0.5982	Remote Similarity	NPD6012	Approved
0.5982	Remote Similarity	NPD6013	Approved
0.5982	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6373	Approved
0.5962	Remote Similarity	NPD7748	Approved
0.5946	Remote Similarity	NPD5701	Approved
0.593	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7102	Approved
0.5929	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7290	Approved
0.5929	Remote Similarity	NPD6883	Approved
0.5922	Remote Similarity	NPD7515	Phase 2
0.5909	Remote Similarity	NPD7331	Phase 2
0.5909	Remote Similarity	NPD3704	Approved
0.59	Remote Similarity	NPD6409	Approved
0.59	Remote Similarity	NPD5330	Approved
0.59	Remote Similarity	NPD7334	Approved
0.59	Remote Similarity	NPD6684	Approved
0.59	Remote Similarity	NPD7521	Approved
0.59	Remote Similarity	NPD7146	Approved
0.59	Remote Similarity	NPD3618	Phase 1
0.5897	Remote Similarity	NPD7500	Approved
0.5895	Remote Similarity	NPD3732	Approved
0.5893	Remote Similarity	NPD7320	Approved
0.5893	Remote Similarity	NPD6011	Approved
0.5877	Remote Similarity	NPD8130	Phase 1
0.5877	Remote Similarity	NPD6847	Approved
0.5877	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6869	Approved
0.5877	Remote Similarity	NPD6617	Approved
0.5872	Remote Similarity	NPD7632	Discontinued
0.5872	Remote Similarity	NPD5211	Phase 2
0.5859	Remote Similarity	NPD3665	Phase 1
0.5859	Remote Similarity	NPD3666	Approved
0.5859	Remote Similarity	NPD3133	Approved
0.5849	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD6882	Approved
0.5826	Remote Similarity	NPD8297	Approved
0.5816	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD3667	Approved
0.5814	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD368	Approved
0.581	Remote Similarity	NPD7900	Approved
0.581	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD3172	Approved
0.5789	Remote Similarity	NPD6421	Discontinued
0.5789	Remote Similarity	NPD2067	Discontinued
0.5784	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD6672	Approved
0.5784	Remote Similarity	NPD5737	Approved
0.5784	Remote Similarity	NPD6903	Approved
0.5773	Remote Similarity	NPD4695	Discontinued
0.5772	Remote Similarity	NPD8273	Phase 1
0.5769	Remote Similarity	NPD5281	Approved
0.5769	Remote Similarity	NPD5284	Approved
0.5769	Remote Similarity	NPD5693	Phase 1
0.5766	Remote Similarity	NPD5141	Approved
0.576	Remote Similarity	NPD7319	Approved
0.5755	Remote Similarity	NPD4629	Approved
0.5755	Remote Similarity	NPD5210	Approved
0.575	Remote Similarity	NPD6927	Phase 3
0.575	Remote Similarity	NPD6319	Approved
0.5743	Remote Similarity	NPD5279	Phase 3
0.5743	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD3194	Approved
0.5732	Remote Similarity	NPD3195	Phase 2
0.5732	Remote Similarity	NPD3196	Approved
0.5732	Remote Similarity	NPD4266	Approved
0.5728	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD6008	Approved
0.5714	Remote Similarity	NPD7641	Discontinued
0.5702	Remote Similarity	NPD8444	Approved
0.5702	Remote Similarity	NPD6413	Approved
0.57	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4786	Approved
0.5691	Remote Similarity	NPD7492	Approved
0.5688	Remote Similarity	NPD4696	Approved
0.5688	Remote Similarity	NPD5285	Approved
0.5688	Remote Similarity	NPD5286	Approved
0.5678	Remote Similarity	NPD6274	Approved
0.5676	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD6412	Phase 2
0.5663	Remote Similarity	NPD342	Phase 1
0.5648	Remote Similarity	NPD4755	Approved
0.5645	Remote Similarity	NPD7507	Approved
0.5645	Remote Similarity	NPD6616	Approved
0.5645	Remote Similarity	NPD8451	Approved
0.5644	Remote Similarity	NPD1696	Phase 3
0.5641	Remote Similarity	NPD1376	Discontinued
0.563	Remote Similarity	NPD7505	Discontinued
0.562	Remote Similarity	NPD6054	Approved
0.5619	Remote Similarity	NPD6079	Approved
0.5619	Remote Similarity	NPD8034	Phase 2
0.5619	Remote Similarity	NPD8035	Phase 2
0.5618	Remote Similarity	NPD7341	Phase 2
0.5614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.56	Remote Similarity	NPD8448	Approved
0.56	Remote Similarity	NPD6695	Phase 3
0.56	Remote Similarity	NPD7078	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