NPASS Compound

Structure

NPC473316 OpenBabel07101718302D 27 30 0 0 1 0 0 0 0 0999 V2000 6.5276 -0.0792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7028 -1.7460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1097 -3.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5608 2.2789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1717 -1.0643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2472 1.2666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8159 -0.4838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4067 1.2666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1340 -0.9632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3269 -2.5332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8159 0.4838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3269 1.5656 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2472 -1.2666 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7782 -1.9482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3269 -1.5656 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4067 -1.2666 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8380 -0.4838 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4067 -2.8322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9752 0.1095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8380 0.4838 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3469 -2.7310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1077 -3.7524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8741 -0.8528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2307 0.6504 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8159 -2.0494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8380 -2.0494 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 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 20 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 6 1 6 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 6 0 0 0 14 21 2 0 0 0 0 14 25 1 0 0 0 0 15 10 1 1 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 6 0 0 0 17 20 1 1 0 0 0 17 27 1 0 0 0 0 18 22 2 0 0 0 0 18 26 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 4 1 1 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.14
Volume:	365.963
LogP:	2.698
LogD:	1.542
LogS:	-3.592
# Rotatable Bonds:	3
TPSA:	98.5
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.481
Synthetic Accessibility Score:	6.122
Fsp3:	0.5
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:	-5.097
MDCK Permeability:	2.534275881771464e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.293
20% Bioavailability (F20%):	0.847
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.242
Plasma Protein Binding (PPB):	82.95719146728516%
Volume Distribution (VD):	0.724
Pgp-substrate:	17.069786071777344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.405
CYP2C19-substrate:	0.325
CYP2C9-inhibitor:	0.806
CYP2C9-substrate:	0.098
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.238
CYP3A4-inhibitor:	0.509
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	9.487
Half-life (T1/2):	0.68

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.628
Drug-inuced Liver Injury (DILI):	0.744
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.718
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.544
Carcinogencity:	0.139
Eye Corrosion:	0.062
Eye Irritation:	0.039
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC473316

Natural Product ID:	NPC473316
*Common Name:**	Elephantin
IUPAC Name:	n.a.
Synonyms:	Elephantin
Standard InCHIKey:	HSTUUCOYVIWGLJ-DXUAHVLSSA-N
Standard InCHI:	InChI=1S/C20H22O7/c1-9(2)5-14(21)25-13-7-11-6-12(24-19(11)23)8-20(4)17(27-20)16-15(13)10(3)18(22)26-16/h5-6,12-13,15-17H,3,7-8H2,1-2,4H3/t12-,13-,15+,16-,17+,20+/m0/s1
SMILES:	CC(=CC(=O)O[C@H]1CC2=C[C@H](OC2=O)C[C@@]2([C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)O2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399907
PubChem CID:	442205
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids 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	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	pED50	=	5.49	n.a.	PMID[451945]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.16	ug ml-1	PMID[451945]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.22	umol/L	PMID[451946]

☑ 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 NPC473316 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	252
0.1-0.2	1531
0.2-0.3	5620
0.3-0.4	11772
0.4-0.5	13007
0.5-0.6	6515
0.6-0.7	2863
0.7-0.8	966
0.8-0.85	95
0.85-0.9	42
0.9-0.95	28
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473330
0.9551	High Similarity	NPC140543
0.954	High Similarity	NPC151770
0.954	High Similarity	NPC166919
0.9432	High Similarity	NPC312042
0.9348	High Similarity	NPC279561
0.9348	High Similarity	NPC473326
0.9348	High Similarity	NPC208233
0.9341	High Similarity	NPC35498
0.9333	High Similarity	NPC476267
0.931	High Similarity	NPC231889
0.931	High Similarity	NPC475703
0.9213	High Similarity	NPC475748
0.9195	High Similarity	NPC50637
0.9121	High Similarity	NPC471147
0.908	High Similarity	NPC319795
0.908	High Similarity	NPC38468
0.908	High Similarity	NPC50362
0.9043	High Similarity	NPC288876
0.9022	High Similarity	NPC475659
0.9	High Similarity	NPC49342
0.9	High Similarity	NPC251385
0.8947	High Similarity	NPC264477
0.8947	High Similarity	NPC477511
0.8925	High Similarity	NPC279621
0.8925	High Similarity	NPC473859
0.8925	High Similarity	NPC17585
0.8913	High Similarity	NPC57405
0.8913	High Similarity	NPC303942
0.8851	High Similarity	NPC272814
0.8817	High Similarity	NPC270013
0.8817	High Similarity	NPC14961
0.8804	High Similarity	NPC125674
0.8804	High Similarity	NPC212486
0.8804	High Similarity	NPC475838
0.8804	High Similarity	NPC228451
0.8764	High Similarity	NPC284902
0.8723	High Similarity	NPC476315
0.871	High Similarity	NPC474247
0.871	High Similarity	NPC474035
0.871	High Similarity	NPC81386
0.8673	High Similarity	NPC477510
0.8673	High Similarity	NPC471143
0.8667	High Similarity	NPC5130
0.8646	High Similarity	NPC477512
0.8632	High Similarity	NPC471140
0.8621	High Similarity	NPC141810
0.8617	High Similarity	NPC471141
0.8602	High Similarity	NPC81419
0.8602	High Similarity	NPC475912
0.8602	High Similarity	NPC179746
0.8602	High Similarity	NPC476300
0.8587	High Similarity	NPC80875
0.8587	High Similarity	NPC473619
0.8587	High Similarity	NPC62815
0.8587	High Similarity	NPC51004
0.8557	High Similarity	NPC474339
0.8557	High Similarity	NPC164598
0.8542	High Similarity	NPC474213
0.8526	High Similarity	NPC230800
0.85	High Similarity	NPC477513
0.8495	Intermediate Similarity	NPC473321
0.8495	Intermediate Similarity	NPC20713
0.8495	Intermediate Similarity	NPC208886
0.8495	Intermediate Similarity	NPC30515
0.8495	Intermediate Similarity	NPC12172
0.8495	Intermediate Similarity	NPC184463
0.8478	Intermediate Similarity	NPC307411
0.8478	Intermediate Similarity	NPC295312
0.8478	Intermediate Similarity	NPC474032
0.8469	Intermediate Similarity	NPC149371
0.8444	Intermediate Similarity	NPC215364
0.8444	Intermediate Similarity	NPC474547
0.8421	Intermediate Similarity	NPC471142
0.8421	Intermediate Similarity	NPC36954
0.8409	Intermediate Similarity	NPC207188
0.8404	Intermediate Similarity	NPC162205
0.8404	Intermediate Similarity	NPC295204
0.8404	Intermediate Similarity	NPC273579
0.8404	Intermediate Similarity	NPC288240
0.84	Intermediate Similarity	NPC223450
0.84	Intermediate Similarity	NPC243998
0.8391	Intermediate Similarity	NPC617
0.8387	Intermediate Similarity	NPC144133
0.8387	Intermediate Similarity	NPC469718
0.8387	Intermediate Similarity	NPC179394
0.8387	Intermediate Similarity	NPC329857
0.8387	Intermediate Similarity	NPC475855
0.837	Intermediate Similarity	NPC202672
0.8367	Intermediate Similarity	NPC476270
0.8367	Intermediate Similarity	NPC47880
0.8367	Intermediate Similarity	NPC201718
0.8352	Intermediate Similarity	NPC204048
0.8351	Intermediate Similarity	NPC471144
0.8333	Intermediate Similarity	NPC138647
0.8333	Intermediate Similarity	NPC470238
0.83	Intermediate Similarity	NPC474741
0.8283	Intermediate Similarity	NPC471148
0.8265	Intermediate Similarity	NPC475949
0.8261	Intermediate Similarity	NPC160138
0.8261	Intermediate Similarity	NPC266957
0.8229	Intermediate Similarity	NPC474947
0.8229	Intermediate Similarity	NPC477922
0.8222	Intermediate Similarity	NPC170286
0.8222	Intermediate Similarity	NPC474472
0.8222	Intermediate Similarity	NPC170377
0.8222	Intermediate Similarity	NPC257358
0.8222	Intermediate Similarity	NPC475947
0.8211	Intermediate Similarity	NPC165383
0.8191	Intermediate Similarity	NPC476004
0.8191	Intermediate Similarity	NPC474761
0.8182	Intermediate Similarity	NPC270126
0.8182	Intermediate Similarity	NPC473332
0.8172	Intermediate Similarity	NPC473715
0.8172	Intermediate Similarity	NPC475902
0.8163	Intermediate Similarity	NPC187268
0.8161	Intermediate Similarity	NPC171204
0.8161	Intermediate Similarity	NPC476028
0.8161	Intermediate Similarity	NPC141789
0.8152	Intermediate Similarity	NPC475461
0.8152	Intermediate Similarity	NPC305475
0.8144	Intermediate Similarity	NPC299396
0.8144	Intermediate Similarity	NPC172998
0.8144	Intermediate Similarity	NPC301596
0.8144	Intermediate Similarity	NPC477921
0.8144	Intermediate Similarity	NPC476275
0.8125	Intermediate Similarity	NPC477131
0.8125	Intermediate Similarity	NPC474338
0.8119	Intermediate Similarity	NPC100487
0.8111	Intermediate Similarity	NPC173609
0.8105	Intermediate Similarity	NPC70251
0.8105	Intermediate Similarity	NPC475881
0.809	Intermediate Similarity	NPC474739
0.809	Intermediate Similarity	NPC281132
0.809	Intermediate Similarity	NPC474510
0.8085	Intermediate Similarity	NPC4986
0.8065	Intermediate Similarity	NPC186148
0.8046	Intermediate Similarity	NPC123360
0.8046	Intermediate Similarity	NPC235906
0.8043	Intermediate Similarity	NPC255307
0.8043	Intermediate Similarity	NPC304509
0.8043	Intermediate Similarity	NPC47958
0.8043	Intermediate Similarity	NPC149725
0.8043	Intermediate Similarity	NPC197903
0.8043	Intermediate Similarity	NPC99395
0.8041	Intermediate Similarity	NPC234339
0.8041	Intermediate Similarity	NPC304886
0.8041	Intermediate Similarity	NPC224689
0.8041	Intermediate Similarity	NPC273197
0.8039	Intermediate Similarity	NPC54737
0.8021	Intermediate Similarity	NPC135776
0.802	Intermediate Similarity	NPC475871
0.802	Intermediate Similarity	NPC475945
0.8	Intermediate Similarity	NPC25684
0.8	Intermediate Similarity	NPC474742
0.8	Intermediate Similarity	NPC15993
0.8	Intermediate Similarity	NPC301477
0.8	Intermediate Similarity	NPC281949
0.7981	Intermediate Similarity	NPC38154
0.7979	Intermediate Similarity	NPC58219
0.7979	Intermediate Similarity	NPC469628
0.7979	Intermediate Similarity	NPC475906
0.7979	Intermediate Similarity	NPC469653
0.7979	Intermediate Similarity	NPC281516
0.7979	Intermediate Similarity	NPC471047
0.7979	Intermediate Similarity	NPC469631
0.7979	Intermediate Similarity	NPC224652
0.7979	Intermediate Similarity	NPC177629
0.7957	Intermediate Similarity	NPC150755
0.7957	Intermediate Similarity	NPC122502
0.7957	Intermediate Similarity	NPC64153
0.7957	Intermediate Similarity	NPC112685
0.7957	Intermediate Similarity	NPC107787
0.7941	Intermediate Similarity	NPC203659
0.7935	Intermediate Similarity	NPC114979
0.7935	Intermediate Similarity	NPC115786
0.7935	Intermediate Similarity	NPC191476
0.7921	Intermediate Similarity	NPC320019
0.7921	Intermediate Similarity	NPC324017
0.7921	Intermediate Similarity	NPC86077
0.7921	Intermediate Similarity	NPC474747
0.7917	Intermediate Similarity	NPC158061
0.7917	Intermediate Similarity	NPC133698
0.7917	Intermediate Similarity	NPC470379
0.7917	Intermediate Similarity	NPC470373
0.7905	Intermediate Similarity	NPC253906
0.7895	Intermediate Similarity	NPC92974
0.7895	Intermediate Similarity	NPC477011
0.7895	Intermediate Similarity	NPC475971
0.7889	Intermediate Similarity	NPC474981
0.7879	Intermediate Similarity	NPC471462
0.7857	Intermediate Similarity	NPC67584
0.7857	Intermediate Similarity	NPC107476
0.7849	Intermediate Similarity	NPC21469
0.7849	Intermediate Similarity	NPC78089
0.7849	Intermediate Similarity	NPC235792
0.7843	Intermediate Similarity	NPC474166
0.7843	Intermediate Similarity	NPC19239
0.7843	Intermediate Similarity	NPC110989
0.7835	Intermediate Similarity	NPC475657

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 NPC473316 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	2136
0.2-0.3	3913
0.3-0.4	1976
0.4-0.5	611
0.5-0.6	232
0.6-0.7	44
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.908	High Similarity	NPD1733	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD1695	Approved
0.7812	Intermediate Similarity	NPD46	Approved
0.7812	Intermediate Similarity	NPD6698	Approved
0.7619	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7838	Discovery
0.7327	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6371	Approved
0.7037	Intermediate Similarity	NPD6008	Approved
0.703	Intermediate Similarity	NPD7983	Approved
0.6979	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6686	Approved
0.6897	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6648	Approved
0.6822	Remote Similarity	NPD5344	Discontinued
0.6814	Remote Similarity	NPD6053	Discontinued
0.6792	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1694	Approved
0.6731	Remote Similarity	NPD5282	Discontinued
0.6726	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4225	Approved
0.6535	Remote Similarity	NPD4249	Approved
0.6476	Remote Similarity	NPD5778	Approved
0.6476	Remote Similarity	NPD5779	Approved
0.6471	Remote Similarity	NPD4250	Approved
0.6471	Remote Similarity	NPD4251	Approved
0.6465	Remote Similarity	NPD5209	Approved
0.6442	Remote Similarity	NPD5785	Approved
0.6441	Remote Similarity	NPD7115	Discovery
0.6423	Remote Similarity	NPD7507	Approved
0.64	Remote Similarity	NPD7154	Phase 3
0.6393	Remote Similarity	NPD7642	Approved
0.6364	Remote Similarity	NPD8513	Phase 3
0.6364	Remote Similarity	NPD8516	Approved
0.6364	Remote Similarity	NPD8517	Approved
0.6364	Remote Similarity	NPD8515	Approved
0.63	Remote Similarity	NPD6435	Approved
0.6275	Remote Similarity	NPD5363	Approved
0.6275	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7319	Approved
0.626	Remote Similarity	NPD7829	Approved
0.626	Remote Similarity	NPD7830	Approved
0.6238	Remote Similarity	NPD5362	Discontinued
0.6214	Remote Similarity	NPD5786	Approved
0.6182	Remote Similarity	NPD7638	Approved
0.6147	Remote Similarity	NPD7839	Suspended
0.6126	Remote Similarity	NPD7640	Approved
0.6126	Remote Similarity	NPD7639	Approved
0.6111	Remote Similarity	NPD8074	Phase 3
0.61	Remote Similarity	NPD4819	Approved
0.61	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5368	Approved
0.61	Remote Similarity	NPD4822	Approved
0.61	Remote Similarity	NPD4820	Approved
0.61	Remote Similarity	NPD4821	Approved
0.6082	Remote Similarity	NPD8039	Approved
0.608	Remote Similarity	NPD7492	Approved
0.6068	Remote Similarity	NPD2067	Discontinued
0.6061	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.605	Remote Similarity	NPD4632	Approved
0.6047	Remote Similarity	NPD7260	Phase 2
0.604	Remote Similarity	NPD5369	Approved
0.6038	Remote Similarity	NPD6101	Approved
0.6038	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6616	Approved
0.6017	Remote Similarity	NPD2204	Approved
0.6016	Remote Similarity	NPD6319	Approved
0.6016	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD6845	Suspended
0.5984	Remote Similarity	NPD7641	Discontinued
0.5984	Remote Similarity	NPD7078	Approved
0.598	Remote Similarity	NPD4270	Approved
0.598	Remote Similarity	NPD4269	Approved
0.5968	Remote Similarity	NPD6015	Approved
0.5968	Remote Similarity	NPD6016	Approved
0.5966	Remote Similarity	NPD8297	Approved
0.5948	Remote Similarity	NPD5697	Approved
0.5943	Remote Similarity	NPD6903	Approved
0.5938	Remote Similarity	NPD7736	Approved
0.5926	Remote Similarity	NPD6411	Approved
0.5926	Remote Similarity	NPD5693	Phase 1
0.592	Remote Similarity	NPD5988	Approved
0.592	Remote Similarity	NPD6370	Approved
0.5906	Remote Similarity	NPD8273	Phase 1
0.5906	Remote Similarity	NPD8451	Approved
0.5905	Remote Similarity	NPD5330	Approved
0.5905	Remote Similarity	NPD7521	Approved
0.5905	Remote Similarity	NPD6684	Approved
0.5905	Remote Similarity	NPD6409	Approved
0.5905	Remote Similarity	NPD7146	Approved
0.5905	Remote Similarity	NPD7334	Approved
0.5902	Remote Similarity	NPD6009	Approved
0.59	Remote Similarity	NPD4271	Approved
0.59	Remote Similarity	NPD4268	Approved
0.5897	Remote Similarity	NPD6899	Approved
0.5897	Remote Similarity	NPD7320	Approved
0.5897	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6881	Approved
0.5887	Remote Similarity	NPD6059	Approved
0.5882	Remote Similarity	NPD6649	Approved
0.5882	Remote Similarity	NPD6650	Approved
0.5873	Remote Similarity	NPD7604	Phase 2
0.5872	Remote Similarity	NPD6399	Phase 3
0.5865	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7128	Approved
0.5862	Remote Similarity	NPD6402	Approved
0.5862	Remote Similarity	NPD6675	Approved
0.5862	Remote Similarity	NPD5739	Approved
0.5859	Remote Similarity	NPD8293	Discontinued
0.5859	Remote Similarity	NPD8448	Approved
0.5854	Remote Similarity	NPD7328	Approved
0.5854	Remote Similarity	NPD7327	Approved
0.5849	Remote Similarity	NPD3573	Approved
0.5847	Remote Similarity	NPD6012	Approved
0.5847	Remote Similarity	NPD6372	Approved
0.5847	Remote Similarity	NPD6014	Approved
0.5847	Remote Similarity	NPD6013	Approved
0.5847	Remote Similarity	NPD6373	Approved
0.584	Remote Similarity	NPD5983	Phase 2
0.584	Remote Similarity	NPD8033	Approved
0.5833	Remote Similarity	NPD5207	Approved
0.5818	Remote Similarity	NPD7900	Approved
0.5818	Remote Similarity	NPD6001	Approved
0.5818	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6412	Phase 2
0.5812	Remote Similarity	NPD5701	Approved
0.5806	Remote Similarity	NPD7516	Approved
0.5798	Remote Similarity	NPD7290	Approved
0.5798	Remote Similarity	NPD6883	Approved
0.5798	Remote Similarity	NPD7102	Approved
0.5794	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5737	Approved
0.5794	Remote Similarity	NPD6672	Approved
0.5784	Remote Similarity	NPD4252	Approved
0.5769	Remote Similarity	NPD5332	Approved
0.5769	Remote Similarity	NPD6110	Phase 1
0.5769	Remote Similarity	NPD5331	Approved
0.5766	Remote Similarity	NPD5695	Phase 3
0.5763	Remote Similarity	NPD6011	Approved
0.576	Remote Similarity	NPD8377	Approved
0.576	Remote Similarity	NPD8294	Approved
0.5755	Remote Similarity	NPD6422	Discontinued
0.5752	Remote Similarity	NPD5696	Approved
0.575	Remote Similarity	NPD6869	Approved
0.575	Remote Similarity	NPD8130	Phase 1
0.575	Remote Similarity	NPD6847	Approved
0.575	Remote Similarity	NPD6617	Approved
0.5745	Remote Similarity	NPD7331	Phase 2
0.5743	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD4790	Discontinued
0.5725	Remote Similarity	NPD8392	Approved
0.5725	Remote Similarity	NPD8390	Approved
0.5725	Remote Similarity	NPD8391	Approved
0.5714	Remote Similarity	NPD8444	Approved
0.5714	Remote Similarity	NPD8378	Approved
0.5714	Remote Similarity	NPD8380	Approved
0.5714	Remote Similarity	NPD8296	Approved
0.5714	Remote Similarity	NPD8379	Approved
0.5714	Remote Similarity	NPD8335	Approved
0.5703	Remote Similarity	NPD8341	Approved
0.5703	Remote Similarity	NPD8340	Approved
0.5703	Remote Similarity	NPD8299	Approved
0.5703	Remote Similarity	NPD8342	Approved
0.5702	Remote Similarity	NPD6882	Approved
0.5688	Remote Similarity	NPD3168	Discontinued
0.5673	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD8080	Discontinued
0.5664	Remote Similarity	NPD6084	Phase 2
0.5664	Remote Similarity	NPD6083	Phase 2
0.5664	Remote Similarity	NPD7902	Approved
0.5659	Remote Similarity	NPD6336	Discontinued
0.5645	Remote Similarity	NPD7500	Approved
0.5645	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD4756	Discovery
0.5638	Remote Similarity	NPD7341	Phase 2
0.5636	Remote Similarity	NPD7637	Suspended
0.5625	Remote Similarity	NPD8328	Phase 3
0.562	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD5211	Phase 2
0.5603	Remote Similarity	NPD7632	Discontinued

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