NPASS Compound

Structure

CID253906 OpenBabel06191716052D 24 28 0 0 1 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 2 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 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -3.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1651 -1.7500 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 10 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 18 1 0 0 0 0 8 12 1 0 0 0 0 8 13 2 0 0 0 0 9 11 2 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 21 2 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 6 0 0 0 15 18 1 0 0 0 0 15 19 1 6 0 0 0 16 20 1 1 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 19 7 1 1 0 0 0 20 9 1 1 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.17
Volume:	336.309
LogP:	3.44
LogD:	3.395
LogS:	-4.773
# Rotatable Bonds:	1
TPSA:	55.9
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.548
Synthetic Accessibility Score:	6.112
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.938
MDCK Permeability:	2.575734288257081e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.934
30% Bioavailability (F30%):	0.223

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.899
Plasma Protein Binding (PPB):	92.64292907714844%
Volume Distribution (VD):	2.367
Pgp-substrate:	8.93615436553955%

ADMET: Metabolism

CYP1A2-inhibitor:	0.175
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.66
CYP2C19-substrate:	0.867
CYP2C9-inhibitor:	0.594
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.201
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.56
CYP3A4-substrate:	0.742

ADMET: Excretion

Clearance (CL):	9.426
Half-life (T1/2):	0.24

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.549
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.238
Rat Oral Acute Toxicity:	0.788
Maximum Recommended Daily Dose:	0.478
Skin Sensitization:	0.168
Carcinogencity:	0.902
Eye Corrosion:	0.051
Eye Irritation:	0.052
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC253906

Natural Product ID:	NPC253906
*Common Name:**	CMURQFGSNXTIKZ-IEYYFSCXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CMURQFGSNXTIKZ-IEYYFSCXSA-N
Standard InCHI:	InChI=1S/C20H24O4/c1-10(2)11-9-20-13(8-12(11)21)19-7-5-6-18(3,4)15(19)14(16(20)24-20)23-17(19)22/h8-10,14-16H,5-7H2,1-4H3/t14-,15-,16-,19-,20+/m0/s1
SMILES:	CC(C)C1=C[C@@]23C(=CC1=O)[C@@]14CCCC(C)(C)[C@@H]1[C@@H]([C@@H]2O3)OC4=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651061
PubChem CID:	50900415
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17461599]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	stem	n.a.	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	Stem bark	Lu Mountain, Jiangxi Province, China	2004-AUG	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26697686]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1700.0	nM	PMID[454364]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[454364]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[454364]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[454364]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[454364]

☑ 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 NPC253906 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	272
0.1-0.2	1532
0.2-0.3	4425
0.3-0.4	7172
0.4-0.5	13089
0.5-0.6	7045
0.6-0.7	6358
0.7-0.8	2448
0.8-0.85	296
0.85-0.9	53
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9515	High Similarity	NPC469370
0.951	High Similarity	NPC180744
0.9151	High Similarity	NPC474846
0.9151	High Similarity	NPC469655
0.9151	High Similarity	NPC469656
0.9065	High Similarity	NPC222834
0.8942	High Similarity	NPC477127
0.8909	High Similarity	NPC469684
0.8846	High Similarity	NPC254202
0.875	High Similarity	NPC475520
0.8739	High Similarity	NPC98249
0.8739	High Similarity	NPC58662
0.8739	High Similarity	NPC13713
0.8739	High Similarity	NPC53396
0.8725	High Similarity	NPC474921
0.8716	High Similarity	NPC472002
0.8716	High Similarity	NPC269530
0.8684	High Similarity	NPC170538
0.8661	High Similarity	NPC473720
0.8661	High Similarity	NPC284707
0.8649	High Similarity	NPC477509
0.8636	High Similarity	NPC33360
0.8636	High Similarity	NPC470120
0.8621	High Similarity	NPC473635
0.8621	High Similarity	NPC293112
0.8614	High Similarity	NPC66581
0.8609	High Similarity	NPC11895
0.8598	High Similarity	NPC133422
0.8596	High Similarity	NPC204731
0.8544	High Similarity	NPC84335
0.8544	High Similarity	NPC38530
0.8534	High Similarity	NPC24651
0.8534	High Similarity	NPC172154
0.8534	High Similarity	NPC81736
0.8529	High Similarity	NPC56369
0.8519	High Similarity	NPC275539
0.8519	High Similarity	NPC189075
0.8505	High Similarity	NPC102352
0.8482	Intermediate Similarity	NPC179626
0.8482	Intermediate Similarity	NPC270478
0.8468	Intermediate Similarity	NPC471204
0.8468	Intermediate Similarity	NPC477126
0.8468	Intermediate Similarity	NPC25909
0.8468	Intermediate Similarity	NPC49451
0.8448	Intermediate Similarity	NPC469789
0.844	Intermediate Similarity	NPC112457
0.8435	Intermediate Similarity	NPC310511
0.8426	Intermediate Similarity	NPC144854
0.8426	Intermediate Similarity	NPC3316
0.8426	Intermediate Similarity	NPC230541
0.8426	Intermediate Similarity	NPC110496
0.8421	Intermediate Similarity	NPC476529
0.8421	Intermediate Similarity	NPC475775
0.8416	Intermediate Similarity	NPC49420
0.8407	Intermediate Similarity	NPC473590
0.8407	Intermediate Similarity	NPC473968
0.8407	Intermediate Similarity	NPC478204
0.8393	Intermediate Similarity	NPC473798
0.8393	Intermediate Similarity	NPC117712
0.8393	Intermediate Similarity	NPC90472
0.8381	Intermediate Similarity	NPC47024
0.8378	Intermediate Similarity	NPC474516
0.8378	Intermediate Similarity	NPC265391
0.8376	Intermediate Similarity	NPC8369
0.8364	Intermediate Similarity	NPC472215
0.8364	Intermediate Similarity	NPC5103
0.8364	Intermediate Similarity	NPC472214
0.8362	Intermediate Similarity	NPC312833
0.8349	Intermediate Similarity	NPC154608
0.8349	Intermediate Similarity	NPC192813
0.8349	Intermediate Similarity	NPC277017
0.8348	Intermediate Similarity	NPC109607
0.8348	Intermediate Similarity	NPC143755
0.8348	Intermediate Similarity	NPC4548
0.8348	Intermediate Similarity	NPC107338
0.8333	Intermediate Similarity	NPC470979
0.8333	Intermediate Similarity	NPC240509
0.8333	Intermediate Similarity	NPC108581
0.8333	Intermediate Similarity	NPC470975
0.8333	Intermediate Similarity	NPC478205
0.8333	Intermediate Similarity	NPC478206
0.8333	Intermediate Similarity	NPC469607
0.8333	Intermediate Similarity	NPC103088
0.8319	Intermediate Similarity	NPC234858
0.8319	Intermediate Similarity	NPC251236
0.8319	Intermediate Similarity	NPC207217
0.8319	Intermediate Similarity	NPC40632
0.8319	Intermediate Similarity	NPC96312
0.8319	Intermediate Similarity	NPC328374
0.8319	Intermediate Similarity	NPC154363
0.8319	Intermediate Similarity	NPC471127
0.8317	Intermediate Similarity	NPC152467
0.8317	Intermediate Similarity	NPC475776
0.8305	Intermediate Similarity	NPC198209
0.8304	Intermediate Similarity	NPC475966
0.8302	Intermediate Similarity	NPC475958
0.8291	Intermediate Similarity	NPC265557
0.8291	Intermediate Similarity	NPC18945
0.8291	Intermediate Similarity	NPC105926
0.8291	Intermediate Similarity	NPC91693
0.8291	Intermediate Similarity	NPC67251
0.8288	Intermediate Similarity	NPC304180
0.8288	Intermediate Similarity	NPC179798
0.8288	Intermediate Similarity	NPC474229
0.8288	Intermediate Similarity	NPC188738
0.8286	Intermediate Similarity	NPC216478
0.8276	Intermediate Similarity	NPC477046
0.8276	Intermediate Similarity	NPC67569
0.8276	Intermediate Similarity	NPC102822
0.8273	Intermediate Similarity	NPC299590
0.8273	Intermediate Similarity	NPC474242
0.8273	Intermediate Similarity	NPC471934
0.8273	Intermediate Similarity	NPC141350
0.8261	Intermediate Similarity	NPC475041
0.8261	Intermediate Similarity	NPC472667
0.8257	Intermediate Similarity	NPC67321
0.8257	Intermediate Similarity	NPC471601
0.8257	Intermediate Similarity	NPC187435
0.8257	Intermediate Similarity	NPC474716
0.8252	Intermediate Similarity	NPC474841
0.8252	Intermediate Similarity	NPC471446
0.8252	Intermediate Similarity	NPC473434
0.8246	Intermediate Similarity	NPC122033
0.8246	Intermediate Similarity	NPC284068
0.8246	Intermediate Similarity	NPC470854
0.8246	Intermediate Similarity	NPC474654
0.8246	Intermediate Similarity	NPC287343
0.8246	Intermediate Similarity	NPC10721
0.8246	Intermediate Similarity	NPC97908
0.8241	Intermediate Similarity	NPC146731
0.8241	Intermediate Similarity	NPC65523
0.8235	Intermediate Similarity	NPC42399
0.8235	Intermediate Similarity	NPC287423
0.8235	Intermediate Similarity	NPC473944
0.8224	Intermediate Similarity	NPC476081
0.8224	Intermediate Similarity	NPC162973
0.822	Intermediate Similarity	NPC476729
0.822	Intermediate Similarity	NPC470922
0.8214	Intermediate Similarity	NPC194951
0.8214	Intermediate Similarity	NPC12046
0.8208	Intermediate Similarity	NPC473219
0.8208	Intermediate Similarity	NPC470761
0.8208	Intermediate Similarity	NPC471413
0.8205	Intermediate Similarity	NPC23786
0.8205	Intermediate Similarity	NPC470265
0.8198	Intermediate Similarity	NPC474567
0.819	Intermediate Similarity	NPC268530
0.819	Intermediate Similarity	NPC154491
0.819	Intermediate Similarity	NPC251226
0.8182	Intermediate Similarity	NPC472439
0.8182	Intermediate Similarity	NPC469916
0.8174	Intermediate Similarity	NPC159928
0.8174	Intermediate Similarity	NPC17772
0.8174	Intermediate Similarity	NPC124676
0.8174	Intermediate Similarity	NPC146280
0.8174	Intermediate Similarity	NPC251310
0.8167	Intermediate Similarity	NPC473620
0.8158	Intermediate Similarity	NPC470793
0.8158	Intermediate Similarity	NPC243981
0.8158	Intermediate Similarity	NPC474734
0.8158	Intermediate Similarity	NPC471816
0.8155	Intermediate Similarity	NPC475657
0.8151	Intermediate Similarity	NPC225049
0.8148	Intermediate Similarity	NPC61442
0.8142	Intermediate Similarity	NPC56448
0.8142	Intermediate Similarity	NPC478212
0.8142	Intermediate Similarity	NPC472757
0.8142	Intermediate Similarity	NPC469496
0.8142	Intermediate Similarity	NPC159333
0.8142	Intermediate Similarity	NPC51978
0.8142	Intermediate Similarity	NPC157441
0.8142	Intermediate Similarity	NPC469463
0.8142	Intermediate Similarity	NPC317210
0.8142	Intermediate Similarity	NPC469454
0.8136	Intermediate Similarity	NPC473979
0.8136	Intermediate Similarity	NPC120724
0.8131	Intermediate Similarity	NPC471412
0.8125	Intermediate Similarity	NPC470960
0.8125	Intermediate Similarity	NPC247031
0.8125	Intermediate Similarity	NPC470246
0.8125	Intermediate Similarity	NPC97939
0.8125	Intermediate Similarity	NPC201992
0.8125	Intermediate Similarity	NPC132790
0.8125	Intermediate Similarity	NPC100329
0.812	Intermediate Similarity	NPC159456
0.812	Intermediate Similarity	NPC470779
0.812	Intermediate Similarity	NPC4021
0.8113	Intermediate Similarity	NPC107806
0.8113	Intermediate Similarity	NPC264378
0.8113	Intermediate Similarity	NPC176845
0.8113	Intermediate Similarity	NPC72647
0.8108	Intermediate Similarity	NPC474243
0.8108	Intermediate Similarity	NPC478210
0.8108	Intermediate Similarity	NPC143706
0.8108	Intermediate Similarity	NPC472534
0.8103	Intermediate Similarity	NPC473636
0.8103	Intermediate Similarity	NPC469380
0.8103	Intermediate Similarity	NPC476960
0.8103	Intermediate Similarity	NPC470186
0.8103	Intermediate Similarity	NPC236918

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 NPC253906 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	1712
0.2-0.3	3738
0.3-0.4	2194
0.4-0.5	778
0.5-0.6	246
0.6-0.7	154
0.7-0.8	86
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8598	High Similarity	NPD5954	Clinical (unspecified phase)
0.8505	High Similarity	NPD6008	Approved
0.8364	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7115	Discovery
0.7647	Intermediate Similarity	NPD1694	Approved
0.7615	Intermediate Similarity	NPD4225	Approved
0.7544	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD3573	Approved
0.7476	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5697	Approved
0.7455	Intermediate Similarity	NPD7638	Approved
0.7438	Intermediate Similarity	NPD6319	Approved
0.7436	Intermediate Similarity	NPD8297	Approved
0.7407	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7900	Approved
0.7391	Intermediate Similarity	NPD6686	Approved
0.7391	Intermediate Similarity	NPD6899	Approved
0.7391	Intermediate Similarity	NPD6881	Approved
0.7387	Intermediate Similarity	NPD7640	Approved
0.7387	Intermediate Similarity	NPD6648	Approved
0.7387	Intermediate Similarity	NPD7639	Approved
0.7368	Intermediate Similarity	NPD5739	Approved
0.7368	Intermediate Similarity	NPD6402	Approved
0.7368	Intermediate Similarity	NPD7128	Approved
0.7368	Intermediate Similarity	NPD6675	Approved
0.7353	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6649	Approved
0.735	Intermediate Similarity	NPD6650	Approved
0.7339	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7492	Approved
0.7333	Intermediate Similarity	NPD6009	Approved
0.7328	Intermediate Similarity	NPD6014	Approved
0.7328	Intermediate Similarity	NPD6373	Approved
0.7328	Intermediate Similarity	NPD6013	Approved
0.7328	Intermediate Similarity	NPD6372	Approved
0.7328	Intermediate Similarity	NPD6012	Approved
0.7321	Intermediate Similarity	NPD5344	Discontinued
0.7304	Intermediate Similarity	NPD5701	Approved
0.7295	Intermediate Similarity	NPD6054	Approved
0.728	Intermediate Similarity	NPD7507	Approved
0.728	Intermediate Similarity	NPD6616	Approved
0.7265	Intermediate Similarity	NPD7290	Approved
0.7265	Intermediate Similarity	NPD7102	Approved
0.7265	Intermediate Similarity	NPD6883	Approved
0.7258	Intermediate Similarity	NPD7604	Phase 2
0.7244	Intermediate Similarity	NPD7319	Approved
0.7241	Intermediate Similarity	NPD7320	Approved
0.7241	Intermediate Similarity	NPD6011	Approved
0.7236	Intermediate Similarity	NPD6016	Approved
0.7236	Intermediate Similarity	NPD5983	Phase 2
0.7236	Intermediate Similarity	NPD6015	Approved
0.7222	Intermediate Similarity	NPD7078	Approved
0.7207	Intermediate Similarity	NPD7902	Approved
0.7203	Intermediate Similarity	NPD6617	Approved
0.7203	Intermediate Similarity	NPD8130	Phase 1
0.7203	Intermediate Similarity	NPD6869	Approved
0.7203	Intermediate Similarity	NPD6847	Approved
0.7177	Intermediate Similarity	NPD6370	Approved
0.7177	Intermediate Similarity	NPD5988	Approved
0.7165	Intermediate Similarity	NPD7736	Approved
0.7156	Intermediate Similarity	NPD6399	Phase 3
0.7154	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.7105	Intermediate Similarity	NPD5211	Phase 2
0.7091	Intermediate Similarity	NPD6001	Approved
0.7091	Intermediate Similarity	NPD7748	Approved
0.7087	Intermediate Similarity	NPD8293	Discontinued
0.708	Intermediate Similarity	NPD5285	Approved
0.708	Intermediate Similarity	NPD5286	Approved
0.708	Intermediate Similarity	NPD4696	Approved
0.7075	Intermediate Similarity	NPD6409	Approved
0.7075	Intermediate Similarity	NPD6684	Approved
0.7075	Intermediate Similarity	NPD5330	Approved
0.7075	Intermediate Similarity	NPD7334	Approved
0.7075	Intermediate Similarity	NPD7521	Approved
0.7075	Intermediate Similarity	NPD7146	Approved
0.7064	Intermediate Similarity	NPD5693	Phase 1
0.7054	Intermediate Similarity	NPD4755	Approved
0.7037	Intermediate Similarity	NPD1695	Approved
0.7008	Intermediate Similarity	NPD6336	Discontinued
0.7	Intermediate Similarity	NPD6053	Discontinued
0.6984	Remote Similarity	NPD8328	Phase 3
0.6983	Remote Similarity	NPD5141	Approved
0.6975	Remote Similarity	NPD6371	Approved
0.6975	Remote Similarity	NPD4634	Approved
0.6972	Remote Similarity	NPD6698	Approved
0.6972	Remote Similarity	NPD46	Approved
0.6967	Remote Similarity	NPD6274	Approved
0.6957	Remote Similarity	NPD5225	Approved
0.6957	Remote Similarity	NPD5226	Approved
0.6957	Remote Similarity	NPD5224	Approved
0.6957	Remote Similarity	NPD4633	Approved
0.6944	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6672	Approved
0.6944	Remote Similarity	NPD5737	Approved
0.6944	Remote Similarity	NPD6903	Approved
0.6935	Remote Similarity	NPD7516	Approved
0.693	Remote Similarity	NPD4700	Approved
0.6917	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD3618	Phase 1
0.6909	Remote Similarity	NPD6079	Approved
0.6909	Remote Similarity	NPD7515	Phase 2
0.6897	Remote Similarity	NPD5174	Approved
0.6897	Remote Similarity	NPD5175	Approved
0.6891	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5328	Approved
0.6875	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5223	Approved
0.687	Remote Similarity	NPD7260	Phase 2
0.6864	Remote Similarity	NPD6412	Phase 2
0.6855	Remote Similarity	NPD7328	Approved
0.6855	Remote Similarity	NPD7327	Approved
0.6842	Remote Similarity	NPD5696	Approved
0.6825	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD8516	Approved
0.6825	Remote Similarity	NPD6921	Approved
0.6825	Remote Similarity	NPD8517	Approved
0.6825	Remote Similarity	NPD8513	Phase 3
0.6825	Remote Similarity	NPD8515	Approved
0.6814	Remote Similarity	NPD4697	Phase 3
0.6814	Remote Similarity	NPD5222	Approved
0.6814	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5221	Approved
0.681	Remote Similarity	NPD7632	Discontinued
0.68	Remote Similarity	NPD7101	Approved
0.68	Remote Similarity	NPD7100	Approved
0.6774	Remote Similarity	NPD6317	Approved
0.6754	Remote Similarity	NPD6083	Phase 2
0.6754	Remote Similarity	NPD5173	Approved
0.6754	Remote Similarity	NPD6084	Phase 2
0.6727	Remote Similarity	NPD6673	Approved
0.6727	Remote Similarity	NPD6904	Approved
0.6727	Remote Similarity	NPD6080	Approved
0.6726	Remote Similarity	NPD5695	Phase 3
0.6723	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6335	Approved
0.672	Remote Similarity	NPD6314	Approved
0.672	Remote Similarity	NPD6313	Approved
0.6696	Remote Similarity	NPD4202	Approved
0.6693	Remote Similarity	NPD8033	Approved
0.6693	Remote Similarity	NPD8379	Approved
0.6693	Remote Similarity	NPD8380	Approved
0.6693	Remote Similarity	NPD8296	Approved
0.6693	Remote Similarity	NPD8335	Approved
0.6693	Remote Similarity	NPD8378	Approved
0.6693	Remote Similarity	NPD7503	Approved
0.6692	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD5128	Approved
0.6641	Remote Similarity	NPD6033	Approved
0.664	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4767	Approved
0.6639	Remote Similarity	NPD4768	Approved
0.6636	Remote Similarity	NPD5208	Approved
0.6614	Remote Similarity	NPD8377	Approved
0.6614	Remote Similarity	NPD8294	Approved
0.661	Remote Similarity	NPD4754	Approved
0.6606	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6051	Approved
0.6574	Remote Similarity	NPD3668	Phase 3
0.6565	Remote Similarity	NPD8074	Phase 3
0.6562	Remote Similarity	NPD6908	Approved
0.6562	Remote Similarity	NPD6909	Approved
0.656	Remote Similarity	NPD6868	Approved
0.6557	Remote Similarity	NPD5248	Approved
0.6557	Remote Similarity	NPD5249	Phase 3
0.6557	Remote Similarity	NPD5250	Approved
0.6557	Remote Similarity	NPD5251	Approved
0.6557	Remote Similarity	NPD5247	Approved
0.6549	Remote Similarity	NPD5779	Approved
0.6549	Remote Similarity	NPD5778	Approved
0.6542	Remote Similarity	NPD3667	Approved
0.6532	Remote Similarity	NPD8133	Approved
0.6518	Remote Similarity	NPD5692	Phase 3
0.6518	Remote Similarity	NPD7838	Discovery
0.6504	Remote Similarity	NPD5217	Approved
0.6504	Remote Similarity	NPD5215	Approved
0.6504	Remote Similarity	NPD5216	Approved
0.6491	Remote Similarity	NPD5282	Discontinued
0.6462	Remote Similarity	NPD6067	Discontinued
0.646	Remote Similarity	NPD5281	Approved
0.646	Remote Similarity	NPD6050	Approved
0.646	Remote Similarity	NPD8034	Phase 2
0.646	Remote Similarity	NPD6411	Approved
0.646	Remote Similarity	NPD5284	Approved
0.646	Remote Similarity	NPD8035	Phase 2
0.646	Remote Similarity	NPD5694	Approved
0.6455	Remote Similarity	NPD6098	Approved
0.6435	Remote Similarity	NPD4629	Approved
0.6435	Remote Similarity	NPD5210	Approved
0.6429	Remote Similarity	NPD4753	Phase 2
0.6423	Remote Similarity	NPD5135	Approved
0.6423	Remote Similarity	NPD5169	Approved
0.6423	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD3666	Approved
0.6422	Remote Similarity	NPD4786	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