NPASS Compound

Structure

NPC471462 OpenBabel07101719252D 30 32 0 0 1 0 0 0 0 0999 V2000 -4.1929 2.9981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0344 -2.4245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0957 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1929 6.4622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6456 1.8925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6929 3.8641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4718 0.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4718 -0.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1929 -1.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2080 1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1929 4.7301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2080 -1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7867 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6929 5.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6929 3.8641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1929 1.2660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8356 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3745 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1929 2.9981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3420 0.9397 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3420 -0.9397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1929 4.7301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3745 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1929 2.9981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6456 -1.8925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6929 5.5962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7867 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6929 2.1321 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 6 1 0 0 0 0 2 12 1 0 0 0 0 3 13 2 0 0 0 0 4 14 1 0 0 0 0 6 15 2 0 0 0 0 7 8 2 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 12 2 0 0 0 0 10 17 1 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 27 1 0 0 0 0 12 22 1 0 0 0 0 13 19 1 0 0 0 0 14 23 2 0 0 0 0 14 27 1 0 0 0 0 15 20 1 0 0 0 0 16 9 1 1 0 0 0 16 18 1 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 6 0 0 0 18 13 1 6 0 0 0 19 24 2 0 0 0 0 19 28 1 0 0 0 0 20 25 2 0 0 0 0 20 29 1 0 0 0 0 21 5 1 1 0 0 0 21 30 1 0 0 0 0 22 26 1 1 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.16
Volume:	415.265
LogP:	1.143
LogD:	0.899
LogS:	-2.797
# Rotatable Bonds:	6
TPSA:	108.36
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	6.141
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.831
MDCK Permeability:	1.6167041394510306e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.13
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107
Plasma Protein Binding (PPB):	60.11445236206055%
Volume Distribution (VD):	1.559
Pgp-substrate:	33.173770904541016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.23
CYP2C19-inhibitor:	0.613
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.648
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.875
CYP3A4-substrate:	0.806

ADMET: Excretion

Clearance (CL):	2.627
Half-life (T1/2):	0.842

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.432
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.775
Rat Oral Acute Toxicity:	0.737
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.737
Carcinogencity:	0.412
Eye Corrosion:	0.005
Eye Irritation:	0.057
Respiratory Toxicity:	0.451

Download Data

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

Natural Product: NPC471462

Natural Product ID:	NPC471462
*Common Name:**	Liatrin
IUPAC Name:	n.a.
Synonyms:	Liatrin
Standard InCHIKey:	PVBVYSOUXOHMEA-ACUBEUJWSA-N
Standard InCHI:	InChI=1S/C22H26O8/c1-6-15(11-27-14(4)23)20(25)29-17-10-21(5)7-8-22(26,30-21)12(2)9-16-18(17)13(3)19(24)28-16/h6-9,16-18,26H,3,10-11H2,1-2,4-5H3/b12-9-,15-6-/t16-,17-,18+,21+,22-/m1/s1
SMILES:	CC=C(COC(=O)C)C(=O)OC1CC2(C=CC(O2)(C(=CC3C1C(=C)C(=O)O3)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251236
PubChem CID:	5281476
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	=	5.41	n.a.	PMID[496072]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.62	ug ml-1	PMID[496072]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.93	umol/L	PMID[496073]

☑ 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 NPC471462 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	205
0.1-0.2	1272
0.2-0.3	4852
0.3-0.4	9025
0.4-0.5	14832
0.5-0.6	7590
0.6-0.7	3864
0.7-0.8	942
0.8-0.85	104
0.85-0.9	9
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9239	High Similarity	NPC474338
0.9	High Similarity	NPC160138
0.8854	High Similarity	NPC187268
0.871	High Similarity	NPC179394
0.871	High Similarity	NPC475855
0.871	High Similarity	NPC144133
0.8646	High Similarity	NPC230800
0.8571	High Similarity	NPC215364
0.8556	High Similarity	NPC250315
0.8542	High Similarity	NPC304886
0.8438	Intermediate Similarity	NPC474247
0.8421	Intermediate Similarity	NPC175842
0.8421	Intermediate Similarity	NPC32494
0.8404	Intermediate Similarity	NPC295312
0.84	Intermediate Similarity	NPC303653
0.84	Intermediate Similarity	NPC189609
0.84	Intermediate Similarity	NPC140591
0.84	Intermediate Similarity	NPC197835
0.84	Intermediate Similarity	NPC291500
0.8367	Intermediate Similarity	NPC471490
0.8351	Intermediate Similarity	NPC471141
0.8351	Intermediate Similarity	NPC471142
0.8333	Intermediate Similarity	NPC59646
0.8333	Intermediate Similarity	NPC125674
0.8333	Intermediate Similarity	NPC228451
0.8333	Intermediate Similarity	NPC475838
0.8298	Intermediate Similarity	NPC475819
0.8298	Intermediate Similarity	NPC476805
0.828	Intermediate Similarity	NPC162071
0.8265	Intermediate Similarity	NPC279621
0.8247	Intermediate Similarity	NPC477131
0.8247	Intermediate Similarity	NPC470521
0.8247	Intermediate Similarity	NPC140543
0.8229	Intermediate Similarity	NPC300312
0.8229	Intermediate Similarity	NPC261607
0.8229	Intermediate Similarity	NPC111114
0.8218	Intermediate Similarity	NPC149371
0.82	Intermediate Similarity	NPC288876
0.8182	Intermediate Similarity	NPC2666
0.8172	Intermediate Similarity	NPC470755
0.8163	Intermediate Similarity	NPC471492
0.8163	Intermediate Similarity	NPC36954
0.8144	Intermediate Similarity	NPC475912
0.8144	Intermediate Similarity	NPC476300
0.8132	Intermediate Similarity	NPC325031
0.8125	Intermediate Similarity	NPC3436
0.8125	Intermediate Similarity	NPC473448
0.8125	Intermediate Similarity	NPC80875
0.8119	Intermediate Similarity	NPC47880
0.81	Intermediate Similarity	NPC471144
0.8095	Intermediate Similarity	NPC38154
0.8085	Intermediate Similarity	NPC469483
0.8085	Intermediate Similarity	NPC305475
0.8085	Intermediate Similarity	NPC475461
0.8085	Intermediate Similarity	NPC284902
0.8081	Intermediate Similarity	NPC473333
0.8081	Intermediate Similarity	NPC301596
0.8081	Intermediate Similarity	NPC299396
0.8081	Intermediate Similarity	NPC476315
0.8065	Intermediate Similarity	NPC158756
0.8061	Intermediate Similarity	NPC323008
0.8061	Intermediate Similarity	NPC262133
0.8061	Intermediate Similarity	NPC198853
0.8061	Intermediate Similarity	NPC470013
0.8061	Intermediate Similarity	NPC470010
0.8061	Intermediate Similarity	NPC476267
0.8061	Intermediate Similarity	NPC167219
0.8058	Intermediate Similarity	NPC474917
0.8058	Intermediate Similarity	NPC100487
0.8041	Intermediate Similarity	NPC133698
0.8041	Intermediate Similarity	NPC470520
0.8021	Intermediate Similarity	NPC64913
0.8021	Intermediate Similarity	NPC225283
0.8021	Intermediate Similarity	NPC242877
0.8	Intermediate Similarity	NPC475960
0.8	Intermediate Similarity	NPC93763
0.8	Intermediate Similarity	NPC40812
0.8	Intermediate Similarity	NPC475703
0.8	Intermediate Similarity	NPC108816
0.8	Intermediate Similarity	NPC72513
0.8	Intermediate Similarity	NPC267231
0.798	Intermediate Similarity	NPC477922
0.798	Intermediate Similarity	NPC475659
0.798	Intermediate Similarity	NPC270013
0.798	Intermediate Similarity	NPC14961
0.798	Intermediate Similarity	NPC67584
0.7979	Intermediate Similarity	NPC255307
0.7961	Intermediate Similarity	NPC475945
0.7961	Intermediate Similarity	NPC475871
0.7959	Intermediate Similarity	NPC81419
0.7959	Intermediate Similarity	NPC179746
0.7957	Intermediate Similarity	NPC473390
0.7957	Intermediate Similarity	NPC169575
0.7957	Intermediate Similarity	NPC131669
0.7957	Intermediate Similarity	NPC40746
0.7957	Intermediate Similarity	NPC116543
0.7941	Intermediate Similarity	NPC474339
0.7941	Intermediate Similarity	NPC150923
0.7941	Intermediate Similarity	NPC474742
0.7941	Intermediate Similarity	NPC164598
0.7938	Intermediate Similarity	NPC474232
0.7938	Intermediate Similarity	NPC473904
0.7938	Intermediate Similarity	NPC51004
0.7938	Intermediate Similarity	NPC474323
0.7938	Intermediate Similarity	NPC206614
0.7938	Intermediate Similarity	NPC106510
0.7938	Intermediate Similarity	NPC71533
0.7921	Intermediate Similarity	NPC308567
0.7921	Intermediate Similarity	NPC255592
0.7921	Intermediate Similarity	NPC261377
0.7921	Intermediate Similarity	NPC141191
0.7921	Intermediate Similarity	NPC473326
0.7917	Intermediate Similarity	NPC476803
0.7917	Intermediate Similarity	NPC202672
0.7905	Intermediate Similarity	NPC26617
0.79	Intermediate Similarity	NPC477921
0.79	Intermediate Similarity	NPC473859
0.79	Intermediate Similarity	NPC213078
0.79	Intermediate Similarity	NPC172998
0.7895	Intermediate Similarity	NPC50637
0.7895	Intermediate Similarity	NPC469910
0.7885	Intermediate Similarity	NPC474741
0.7885	Intermediate Similarity	NPC203659
0.7879	Intermediate Similarity	NPC127019
0.7879	Intermediate Similarity	NPC474035
0.7879	Intermediate Similarity	NPC473316
0.7879	Intermediate Similarity	NPC81386
0.7879	Intermediate Similarity	NPC475832
0.7879	Intermediate Similarity	NPC473330
0.7879	Intermediate Similarity	NPC469632
0.7879	Intermediate Similarity	NPC475927
0.7872	Intermediate Similarity	NPC114979
0.7872	Intermediate Similarity	NPC191476
0.7872	Intermediate Similarity	NPC476804
0.7864	Intermediate Similarity	NPC86077
0.7864	Intermediate Similarity	NPC474747
0.7857	Intermediate Similarity	NPC473321
0.7857	Intermediate Similarity	NPC158061
0.7857	Intermediate Similarity	NPC12172
0.7857	Intermediate Similarity	NPC131209
0.7857	Intermediate Similarity	NPC30515
0.7857	Intermediate Similarity	NPC208886
0.7857	Intermediate Similarity	NPC475925
0.7857	Intermediate Similarity	NPC184463
0.7857	Intermediate Similarity	NPC184063
0.7849	Intermediate Similarity	NPC229825
0.7835	Intermediate Similarity	NPC166919
0.7835	Intermediate Similarity	NPC307411
0.7835	Intermediate Similarity	NPC205548
0.7835	Intermediate Similarity	NPC139418
0.7835	Intermediate Similarity	NPC473564
0.7822	Intermediate Similarity	NPC213947
0.7822	Intermediate Similarity	NPC161493
0.7822	Intermediate Similarity	NPC108475
0.7822	Intermediate Similarity	NPC169205
0.7822	Intermediate Similarity	NPC170143
0.781	Intermediate Similarity	NPC223450
0.78	Intermediate Similarity	NPC213698
0.78	Intermediate Similarity	NPC170120
0.78	Intermediate Similarity	NPC234339
0.78	Intermediate Similarity	NPC273197
0.78	Intermediate Similarity	NPC52044
0.7789	Intermediate Similarity	NPC261380
0.7789	Intermediate Similarity	NPC125290
0.7789	Intermediate Similarity	NPC165162
0.7788	Intermediate Similarity	NPC472755
0.7788	Intermediate Similarity	NPC110989
0.7778	Intermediate Similarity	NPC469645
0.7778	Intermediate Similarity	NPC212486
0.7778	Intermediate Similarity	NPC469692
0.7778	Intermediate Similarity	NPC135776
0.7778	Intermediate Similarity	NPC476049
0.7778	Intermediate Similarity	NPC123360
0.7767	Intermediate Similarity	NPC128733
0.7767	Intermediate Similarity	NPC185141
0.7767	Intermediate Similarity	NPC110443
0.7767	Intermediate Similarity	NPC133907
0.7767	Intermediate Similarity	NPC473332
0.7767	Intermediate Similarity	NPC46998
0.7766	Intermediate Similarity	NPC318468
0.7766	Intermediate Similarity	NPC475947
0.7755	Intermediate Similarity	NPC476004
0.7755	Intermediate Similarity	NPC475748
0.7755	Intermediate Similarity	NPC312042
0.7755	Intermediate Similarity	NPC19087
0.7755	Intermediate Similarity	NPC129419
0.7755	Intermediate Similarity	NPC473619
0.7755	Intermediate Similarity	NPC474761
0.7745	Intermediate Similarity	NPC208233
0.7745	Intermediate Similarity	NPC83895
0.7745	Intermediate Similarity	NPC279561
0.7745	Intermediate Similarity	NPC203627
0.7745	Intermediate Similarity	NPC221615
0.7745	Intermediate Similarity	NPC187761
0.7742	Intermediate Similarity	NPC24417
0.7742	Intermediate Similarity	NPC141810
0.7736	Intermediate Similarity	NPC477513
0.7732	Intermediate Similarity	NPC233551
0.7732	Intermediate Similarity	NPC280621
0.7732	Intermediate Similarity	NPC48338

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 NPC471462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1847
0.2-0.3	3710
0.3-0.4	2281
0.4-0.5	763
0.5-0.6	289
0.6-0.7	68
0.7-0.8	7
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7905	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD46	Approved
0.74	Intermediate Similarity	NPD6698	Approved
0.7364	Intermediate Similarity	NPD6371	Approved
0.7353	Intermediate Similarity	NPD5282	Discontinued
0.7327	Intermediate Similarity	NPD7983	Approved
0.73	Intermediate Similarity	NPD1695	Approved
0.7297	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7838	Discovery
0.7228	Intermediate Similarity	NPD5785	Approved
0.7182	Intermediate Similarity	NPD6686	Approved
0.7071	Intermediate Similarity	NPD5363	Approved
0.7071	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7839	Suspended
0.7	Intermediate Similarity	NPD4249	Approved
0.6931	Remote Similarity	NPD4251	Approved
0.6931	Remote Similarity	NPD4250	Approved
0.6923	Remote Similarity	NPD5779	Approved
0.6923	Remote Similarity	NPD5778	Approved
0.6916	Remote Similarity	NPD4225	Approved
0.6891	Remote Similarity	NPD8513	Phase 3
0.6891	Remote Similarity	NPD8516	Approved
0.6891	Remote Similarity	NPD8515	Approved
0.6891	Remote Similarity	NPD8517	Approved
0.6869	Remote Similarity	NPD7154	Phase 3
0.6768	Remote Similarity	NPD4270	Approved
0.6768	Remote Similarity	NPD4269	Approved
0.67	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6638	Remote Similarity	NPD6053	Discontinued
0.6636	Remote Similarity	NPD5344	Discontinued
0.6613	Remote Similarity	NPD8074	Phase 3
0.66	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1694	Approved
0.6566	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4819	Approved
0.6566	Remote Similarity	NPD4821	Approved
0.6566	Remote Similarity	NPD4820	Approved
0.6566	Remote Similarity	NPD4822	Approved
0.6566	Remote Similarity	NPD4252	Approved
0.6555	Remote Similarity	NPD7115	Discovery
0.6545	Remote Similarity	NPD6648	Approved
0.6508	Remote Similarity	NPD7319	Approved
0.6504	Remote Similarity	NPD7642	Approved
0.6471	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5209	Approved
0.6417	Remote Similarity	NPD7500	Approved
0.6412	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7507	Approved
0.6396	Remote Similarity	NPD7640	Approved
0.6396	Remote Similarity	NPD7639	Approved
0.6371	Remote Similarity	NPD7829	Approved
0.6371	Remote Similarity	NPD7830	Approved
0.6364	Remote Similarity	NPD4271	Approved
0.6364	Remote Similarity	NPD4268	Approved
0.6355	Remote Similarity	NPD7637	Suspended
0.6321	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6101	Approved
0.632	Remote Similarity	NPD7492	Approved
0.6306	Remote Similarity	NPD7638	Approved
0.6275	Remote Similarity	NPD6435	Approved
0.627	Remote Similarity	NPD8451	Approved
0.627	Remote Similarity	NPD6616	Approved
0.626	Remote Similarity	NPD6054	Approved
0.6239	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8448	Approved
0.622	Remote Similarity	NPD7078	Approved
0.6214	Remote Similarity	NPD5332	Approved
0.6214	Remote Similarity	NPD5331	Approved
0.621	Remote Similarity	NPD6016	Approved
0.621	Remote Similarity	NPD6015	Approved
0.6207	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6411	Approved
0.62	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8340	Approved
0.619	Remote Similarity	NPD8299	Approved
0.619	Remote Similarity	NPD8342	Approved
0.619	Remote Similarity	NPD8341	Approved
0.6176	Remote Similarity	NPD4790	Discontinued
0.6172	Remote Similarity	NPD7736	Approved
0.6168	Remote Similarity	NPD5370	Suspended
0.616	Remote Similarity	NPD5988	Approved
0.616	Remote Similarity	NPD6370	Approved
0.6142	Remote Similarity	NPD8273	Phase 1
0.6134	Remote Similarity	NPD2204	Approved
0.6129	Remote Similarity	NPD6319	Approved
0.6129	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6008	Approved
0.6098	Remote Similarity	NPD7641	Discontinued
0.6098	Remote Similarity	NPD7328	Approved
0.6098	Remote Similarity	NPD7327	Approved
0.6083	Remote Similarity	NPD6882	Approved
0.608	Remote Similarity	NPD8444	Approved
0.608	Remote Similarity	NPD8033	Approved
0.6078	Remote Similarity	NPD5368	Approved
0.6077	Remote Similarity	NPD8391	Approved
0.6077	Remote Similarity	NPD8390	Approved
0.6077	Remote Similarity	NPD8392	Approved
0.6055	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD8294	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.6	Remote Similarity	NPD8377	Approved
0.5969	Remote Similarity	NPD8293	Discontinued
0.5952	Remote Similarity	NPD8296	Approved
0.5952	Remote Similarity	NPD8335	Approved
0.5952	Remote Similarity	NPD7503	Approved
0.5952	Remote Similarity	NPD8380	Approved
0.5952	Remote Similarity	NPD8378	Approved
0.5952	Remote Similarity	NPD8379	Approved
0.5941	Remote Similarity	NPD4756	Discovery
0.5932	Remote Similarity	NPD5697	Approved
0.5932	Remote Similarity	NPD6412	Phase 2
0.5909	Remote Similarity	NPD7260	Phase 2
0.5906	Remote Similarity	NPD8080	Discontinued
0.59	Remote Similarity	NPD8039	Approved
0.5893	Remote Similarity	NPD5695	Phase 3
0.5887	Remote Similarity	NPD6009	Approved
0.5887	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD6899	Approved
0.5882	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD5696	Approved
0.5868	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7632	Discontinued
0.5859	Remote Similarity	NPD8328	Phase 3
0.5847	Remote Similarity	NPD4211	Phase 1
0.5833	Remote Similarity	NPD6372	Approved
0.5833	Remote Similarity	NPD6013	Approved
0.5833	Remote Similarity	NPD5956	Approved
0.5833	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD6014	Approved
0.5833	Remote Similarity	NPD6373	Approved
0.5833	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD8266	Approved
0.5827	Remote Similarity	NPD8268	Approved
0.5827	Remote Similarity	NPD8267	Approved
0.5827	Remote Similarity	NPD8269	Approved
0.582	Remote Similarity	NPD8297	Approved
0.5789	Remote Similarity	NPD7902	Approved
0.5789	Remote Similarity	NPD6083	Phase 2
0.5789	Remote Similarity	NPD6084	Phase 2
0.5785	Remote Similarity	NPD6421	Discontinued
0.5785	Remote Similarity	NPD6883	Approved
0.5785	Remote Similarity	NPD7290	Approved
0.5785	Remote Similarity	NPD7102	Approved
0.5772	Remote Similarity	NPD8133	Approved
0.5772	Remote Similarity	NPD4632	Approved
0.5766	Remote Similarity	NPD5281	Approved
0.5766	Remote Similarity	NPD5284	Approved
0.576	Remote Similarity	NPD7505	Discontinued
0.5755	Remote Similarity	NPD6110	Phase 1
0.575	Remote Similarity	NPD6011	Approved
0.575	Remote Similarity	NPD7320	Approved
0.5746	Remote Similarity	NPD6845	Suspended
0.5738	Remote Similarity	NPD6847	Approved
0.5738	Remote Similarity	NPD8130	Phase 1
0.5738	Remote Similarity	NPD6869	Approved
0.5738	Remote Similarity	NPD6617	Approved
0.5726	Remote Similarity	NPD5211	Phase 2
0.5714	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD6675	Approved
0.5714	Remote Similarity	NPD5739	Approved
0.5714	Remote Similarity	NPD6402	Approved
0.5703	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD5207	Approved
0.5667	Remote Similarity	NPD5701	Approved
0.5664	Remote Similarity	NPD7748	Approved
0.566	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD2067	Discontinued
0.5656	Remote Similarity	NPD4634	Approved
0.5636	Remote Similarity	NPD6903	Approved
0.5635	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.563	Remote Similarity	NPD5141	Approved
0.5625	Remote Similarity	NPD5693	Phase 1
0.562	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD5210	Approved
0.5614	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD4629	Approved
0.561	Remote Similarity	NPD1719	Phase 1
0.5607	Remote Similarity	NPD6695	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