NPASS Compound

Structure

NPC472413 OpenBabel07101719142D 33 36 0 0 1 0 0 0 0 0999 V2000 -4.5017 -2.2027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5996 0.5736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3899 -1.8842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7886 -3.7349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2593 -1.3687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4167 -1.8552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2593 -0.3957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1851 -3.2178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0582 -2.7885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5741 -1.3687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4167 0.0907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2184 -3.1069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0875 0.1991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1287 0.0332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7315 0.0907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5607 -1.9553 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9837 -0.1796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4382 -2.0864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1375 -3.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5741 -0.3957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4652 -2.4910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8889 -0.3957 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4119 -0.6247 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7872 -1.3634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5329 -0.9828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1858 -3.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6510 -0.7231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1646 -1.5657 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2545 0.3802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4582 -0.6821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1148 -4.1394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6187 -0.6214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 9 1 0 0 0 0 8 12 2 0 0 0 0 9 16 1 0 0 0 0 10 20 2 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 23 1 0 0 0 0 15 20 1 0 0 0 0 16 1 1 6 0 0 0 16 25 1 0 0 0 0 17 2 1 1 0 0 0 17 25 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 21 26 1 0 0 0 0 21 28 1 6 0 0 0 22 15 1 1 0 0 0 22 24 1 0 0 0 0 22 29 1 0 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 28 1 6 0 0 0 25 31 2 0 0 0 0 26 32 2 0 0 0 0 27 29 2 0 0 0 0 27 33 1 0 0 0 0 28 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	447.24
Volume:	481.048
LogP:	3.308
LogD:	1.33
LogS:	-3.062
# Rotatable Bonds:	2
TPSA:	83.47
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.677
Synthetic Accessibility Score:	5.622
Fsp3:	0.464
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.807
MDCK Permeability:	1.548420732433442e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.237
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.308
Plasma Protein Binding (PPB):	97.05301666259766%
Volume Distribution (VD):	2.263
Pgp-substrate:	1.301910400390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.203
CYP2C19-inhibitor:	0.709
CYP2C19-substrate:	0.744
CYP2C9-inhibitor:	0.799
CYP2C9-substrate:	0.17
CYP2D6-inhibitor:	0.441
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.932
CYP3A4-substrate:	0.617

ADMET: Excretion

Clearance (CL):	9.239
Half-life (T1/2):	0.339

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.167
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.707
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.258
Carcinogencity:	0.063
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC472413

Natural Product ID:	NPC472413
*Common Name:**	XDZFFBKZLFLEIL-JMFUEJSISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XDZFFBKZLFLEIL-JMFUEJSISA-N
Standard InCHI:	InChI=1S/C28H33NO4/c1-16-9-8-12-21-26(32)19(4)18(3)24-22(15-20-10-6-5-7-11-20)29-27(33)28(21,24)23(30)14-13-17(2)25(16)31/h5-8,10-14,16-17,21-24,30H,9,15H2,1-4H3,(H,29,33)/b12-8+,14-13+/t16-,17-,21-,22-,23+,24-,28+/m0/s1
SMILES:	C[C@H]1/C=C/[C@@H](O)[C@@]23C(=N[C@H]([C@@H]2C(=C(C(=O)[C@@H]3/C=C/C[C@@H](C1=O)C)C)C)Cc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3402241
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001821] Cytochalasans

*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
NPO33244	crodyceps taii	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25863432]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	32280.0	nM	PMID[449600]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	200000.0	nM	PMID[449600]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23670.0	nM	PMID[449600]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29840.0	nM	PMID[449600]

☑ 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 NPC472413 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	111
0.1-0.2	618
0.2-0.3	2170
0.3-0.4	7087
0.4-0.5	22558
0.5-0.6	9008
0.6-0.7	1048
0.7-0.8	84
0.8-0.85	6
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.936	High Similarity	NPC183722
0.92	High Similarity	NPC116057
0.9106	High Similarity	NPC472415
0.9	High Similarity	NPC208725
0.896	High Similarity	NPC472414
0.875	High Similarity	NPC71271
0.8409	Intermediate Similarity	NPC42423
0.8222	Intermediate Similarity	NPC113325
0.8222	Intermediate Similarity	NPC279045
0.8148	Intermediate Similarity	NPC228511
0.8016	Intermediate Similarity	NPC188010
0.7986	Intermediate Similarity	NPC239770
0.7895	Intermediate Similarity	NPC278097
0.7883	Intermediate Similarity	NPC90693
0.7883	Intermediate Similarity	NPC64897
0.777	Intermediate Similarity	NPC175870
0.771	Intermediate Similarity	NPC190663
0.7681	Intermediate Similarity	NPC328070
0.7676	Intermediate Similarity	NPC108852
0.7676	Intermediate Similarity	NPC261709
0.7676	Intermediate Similarity	NPC111586
0.766	Intermediate Similarity	NPC322526
0.7639	Intermediate Similarity	NPC49565
0.7639	Intermediate Similarity	NPC262216
0.7594	Intermediate Similarity	NPC160493
0.7589	Intermediate Similarity	NPC473052
0.7589	Intermediate Similarity	NPC473055
0.7576	Intermediate Similarity	NPC80150
0.7576	Intermediate Similarity	NPC478014
0.7576	Intermediate Similarity	NPC478015
0.7576	Intermediate Similarity	NPC478016
0.7535	Intermediate Similarity	NPC153007
0.7535	Intermediate Similarity	NPC471201
0.7518	Intermediate Similarity	NPC295478
0.7424	Intermediate Similarity	NPC310467
0.7348	Intermediate Similarity	NPC169328
0.7347	Intermediate Similarity	NPC31171
0.7347	Intermediate Similarity	NPC237240
0.7339	Intermediate Similarity	NPC474563
0.7299	Intermediate Similarity	NPC47667
0.7295	Intermediate Similarity	NPC317280
0.7295	Intermediate Similarity	NPC329387
0.7267	Intermediate Similarity	NPC470274
0.7244	Intermediate Similarity	NPC307903
0.7244	Intermediate Similarity	NPC140251
0.7241	Intermediate Similarity	NPC150712
0.72	Intermediate Similarity	NPC201692
0.72	Intermediate Similarity	NPC471317
0.7177	Intermediate Similarity	NPC469457
0.7165	Intermediate Similarity	NPC274089
0.7165	Intermediate Similarity	NPC191215
0.7143	Intermediate Similarity	NPC194390
0.7143	Intermediate Similarity	NPC88267
0.7143	Intermediate Similarity	NPC224610
0.7143	Intermediate Similarity	NPC113326
0.7133	Intermediate Similarity	NPC477680
0.7089	Intermediate Similarity	NPC71205
0.7067	Intermediate Similarity	NPC173934
0.7063	Intermediate Similarity	NPC202613
0.7054	Intermediate Similarity	NPC475282
0.705	Intermediate Similarity	NPC477248
0.705	Intermediate Similarity	NPC477249
0.7029	Intermediate Similarity	NPC35996
0.7023	Intermediate Similarity	NPC471188
0.7	Intermediate Similarity	NPC328824
0.7	Intermediate Similarity	NPC476290
0.6993	Remote Similarity	NPC4108
0.6978	Remote Similarity	NPC285394
0.697	Remote Similarity	NPC287055
0.697	Remote Similarity	NPC306977
0.697	Remote Similarity	NPC206414
0.697	Remote Similarity	NPC242957
0.697	Remote Similarity	NPC474584
0.6962	Remote Similarity	NPC476750
0.6962	Remote Similarity	NPC67080
0.6959	Remote Similarity	NPC161069
0.6944	Remote Similarity	NPC313663
0.6943	Remote Similarity	NPC476194
0.694	Remote Similarity	NPC9274
0.6934	Remote Similarity	NPC45777
0.6934	Remote Similarity	NPC477061
0.6923	Remote Similarity	NPC49272
0.6923	Remote Similarity	NPC93343
0.6912	Remote Similarity	NPC237420
0.6912	Remote Similarity	NPC314992
0.6911	Remote Similarity	NPC58674
0.6908	Remote Similarity	NPC227905
0.6908	Remote Similarity	NPC146097
0.6908	Remote Similarity	NPC476757
0.6908	Remote Similarity	NPC339338
0.6897	Remote Similarity	NPC132847
0.6894	Remote Similarity	NPC476269
0.6887	Remote Similarity	NPC44649
0.6887	Remote Similarity	NPC475578
0.6875	Remote Similarity	NPC246913
0.6875	Remote Similarity	NPC15506
0.686	Remote Similarity	NPC316108
0.6857	Remote Similarity	NPC12881
0.6857	Remote Similarity	NPC473938
0.6857	Remote Similarity	NPC140118
0.6855	Remote Similarity	NPC25565
0.6853	Remote Similarity	NPC478147
0.6842	Remote Similarity	NPC273814
0.6842	Remote Similarity	NPC473541
0.6842	Remote Similarity	NPC470253
0.6835	Remote Similarity	NPC84281
0.6835	Remote Similarity	NPC213126
0.6835	Remote Similarity	NPC169485
0.6835	Remote Similarity	NPC317474
0.6835	Remote Similarity	NPC291027
0.6825	Remote Similarity	NPC12730
0.6822	Remote Similarity	NPC211551
0.6822	Remote Similarity	NPC471186
0.6818	Remote Similarity	NPC265513
0.6818	Remote Similarity	NPC185404
0.6812	Remote Similarity	NPC472679
0.6812	Remote Similarity	NPC474223
0.6812	Remote Similarity	NPC475827
0.6812	Remote Similarity	NPC472680
0.6809	Remote Similarity	NPC4974
0.6806	Remote Similarity	NPC472388
0.68	Remote Similarity	NPC475439
0.68	Remote Similarity	NPC289201
0.68	Remote Similarity	NPC473501
0.6797	Remote Similarity	NPC94602
0.6792	Remote Similarity	NPC156348
0.6791	Remote Similarity	NPC1986
0.6791	Remote Similarity	NPC474544
0.6786	Remote Similarity	NPC6975
0.6783	Remote Similarity	NPC296712
0.6776	Remote Similarity	NPC138775
0.6774	Remote Similarity	NPC472761
0.6774	Remote Similarity	NPC206764
0.6772	Remote Similarity	NPC153694
0.6772	Remote Similarity	NPC211525
0.6772	Remote Similarity	NPC264728
0.677	Remote Similarity	NPC470069
0.677	Remote Similarity	NPC52059
0.6769	Remote Similarity	NPC85560
0.6769	Remote Similarity	NPC475800
0.6769	Remote Similarity	NPC244933
0.6767	Remote Similarity	NPC218855
0.6765	Remote Similarity	NPC2265
0.6763	Remote Similarity	NPC472981
0.6763	Remote Similarity	NPC476234
0.6761	Remote Similarity	NPC328997
0.6761	Remote Similarity	NPC294050
0.6755	Remote Similarity	NPC473922
0.6752	Remote Similarity	NPC114808
0.6748	Remote Similarity	NPC476749
0.6744	Remote Similarity	NPC329282
0.6741	Remote Similarity	NPC93181
0.6741	Remote Similarity	NPC33742
0.6736	Remote Similarity	NPC225103
0.6733	Remote Similarity	NPC91953
0.6727	Remote Similarity	NPC120667
0.6727	Remote Similarity	NPC278272
0.6716	Remote Similarity	NPC471481
0.6715	Remote Similarity	NPC222968
0.6715	Remote Similarity	NPC61651
0.6715	Remote Similarity	NPC80605
0.6715	Remote Similarity	NPC254088
0.6715	Remote Similarity	NPC323440
0.6714	Remote Similarity	NPC109151
0.6714	Remote Similarity	NPC474862
0.6714	Remote Similarity	NPC252878
0.6712	Remote Similarity	NPC3202
0.6712	Remote Similarity	NPC80599
0.6708	Remote Similarity	NPC471394
0.6708	Remote Similarity	NPC293164
0.6693	Remote Similarity	NPC54647
0.6692	Remote Similarity	NPC321670
0.6692	Remote Similarity	NPC319579
0.6692	Remote Similarity	NPC474057
0.6692	Remote Similarity	NPC323007
0.6691	Remote Similarity	NPC197470
0.6691	Remote Similarity	NPC476190
0.6691	Remote Similarity	NPC470585
0.669	Remote Similarity	NPC473443
0.6689	Remote Similarity	NPC474659
0.6689	Remote Similarity	NPC23894
0.6687	Remote Similarity	NPC88378
0.6687	Remote Similarity	NPC211713
0.6687	Remote Similarity	NPC101207
0.6686	Remote Similarity	NPC475649
0.6667	Remote Similarity	NPC276949
0.6667	Remote Similarity	NPC15850
0.6667	Remote Similarity	NPC474725
0.6667	Remote Similarity	NPC474254
0.6667	Remote Similarity	NPC234637
0.6667	Remote Similarity	NPC130591
0.6667	Remote Similarity	NPC247976
0.6667	Remote Similarity	NPC35850
0.6667	Remote Similarity	NPC135121
0.6667	Remote Similarity	NPC316553
0.6667	Remote Similarity	NPC46427
0.6667	Remote Similarity	NPC474159
0.6667	Remote Similarity	NPC40488
0.6667	Remote Similarity	NPC197921
0.6667	Remote Similarity	NPC469666

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 NPC472413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	105
0.1-0.2	421
0.2-0.3	848
0.3-0.4	2103
0.4-0.5	3521
0.5-0.6	1816
0.6-0.7	330
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7556	Intermediate Similarity	NPD6325	Discontinued
0.75	Intermediate Similarity	NPD5981	Approved
0.7347	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD3644	Approved
0.7344	Intermediate Similarity	NPD3642	Approved
0.7344	Intermediate Similarity	NPD3643	Approved
0.7174	Intermediate Similarity	NPD6330	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6406	Approved
0.709	Intermediate Similarity	NPD7522	Discontinued
0.7021	Intermediate Similarity	NPD7084	Phase 3
0.6978	Remote Similarity	NPD5159	Phase 2
0.6978	Remote Similarity	NPD5157	Phase 1
0.6978	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7714	Approved
0.6944	Remote Similarity	NPD7715	Approved
0.6929	Remote Similarity	NPD6647	Phase 2
0.6912	Remote Similarity	NPD2217	Approved
0.6912	Remote Similarity	NPD2218	Phase 2
0.6911	Remote Similarity	NPD4814	Discontinued
0.6906	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3123	Discovery
0.685	Remote Similarity	NPD4719	Phase 2
0.6835	Remote Similarity	NPD3132	Approved
0.6835	Remote Similarity	NPD3131	Approved
0.6835	Remote Similarity	NPD4217	Approved
0.6835	Remote Similarity	NPD2611	Approved
0.6835	Remote Similarity	NPD4216	Approved
0.6835	Remote Similarity	NPD4218	Approved
0.6835	Remote Similarity	NPD2608	Approved
0.6835	Remote Similarity	NPD2609	Approved
0.6835	Remote Similarity	NPD2612	Approved
0.6835	Remote Similarity	NPD2610	Approved
0.6835	Remote Similarity	NPD4215	Approved
0.6829	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1018	Approved
0.6806	Remote Similarity	NPD4738	Phase 2
0.6806	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD8172	Phase 2
0.6803	Remote Similarity	NPD8173	Phase 2
0.6781	Remote Similarity	NPD8416	Discontinued
0.6772	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7094	Approved
0.6716	Remote Similarity	NPD6858	Approved
0.6716	Remote Similarity	NPD2607	Approved
0.6714	Remote Similarity	NPD5618	Discontinued
0.6691	Remote Similarity	NPD1348	Approved
0.669	Remote Similarity	NPD3136	Phase 2
0.6689	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7011	Discontinued
0.6667	Remote Similarity	NPD7295	Approved
0.6667	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4479	Discontinued
0.6641	Remote Similarity	NPD467	Phase 1
0.6622	Remote Similarity	NPD8643	Discontinued
0.6621	Remote Similarity	NPD2613	Approved
0.6618	Remote Similarity	NPD1711	Phase 2
0.6613	Remote Similarity	NPD6690	Approved
0.6577	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7725	Approved
0.6571	Remote Similarity	NPD7342	Discontinued
0.6565	Remote Similarity	NPD5717	Approved
0.6558	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD8265	Approved
0.6552	Remote Similarity	NPD3626	Phase 3
0.6547	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD3598	Phase 3
0.6538	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4657	Approved
0.6535	Remote Similarity	NPD4655	Approved
0.6533	Remote Similarity	NPD6852	Discontinued
0.6528	Remote Similarity	NPD2160	Approved
0.6528	Remote Similarity	NPD2628	Approved
0.6528	Remote Similarity	NPD2625	Approved
0.6528	Remote Similarity	NPD2626	Approved
0.6528	Remote Similarity	NPD2627	Approved
0.6528	Remote Similarity	NPD2159	Approved
0.6515	Remote Similarity	NPD5706	Approved
0.6515	Remote Similarity	NPD5705	Approved
0.6515	Remote Similarity	NPD5704	Approved
0.6513	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3400	Discontinued
0.6489	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3088	Approved
0.6486	Remote Similarity	NPD3090	Approved
0.6486	Remote Similarity	NPD4746	Phase 3
0.6486	Remote Similarity	NPD2574	Discontinued
0.6486	Remote Similarity	NPD3615	Approved
0.6486	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2571	Approved
0.6486	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2570	Approved
0.6486	Remote Similarity	NPD3614	Approved
0.6486	Remote Similarity	NPD3087	Approved
0.6486	Remote Similarity	NPD3616	Approved
0.6486	Remote Similarity	NPD8118	Discontinued
0.6486	Remote Similarity	NPD2573	Approved
0.6486	Remote Similarity	NPD4745	Approved
0.6486	Remote Similarity	NPD2566	Approved
0.6486	Remote Similarity	NPD3089	Approved
0.6484	Remote Similarity	NPD253	Approved
0.6479	Remote Similarity	NPD3603	Phase 3
0.6475	Remote Similarity	NPD6065	Approved
0.6475	Remote Similarity	NPD1758	Phase 1
0.6466	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD855	Approved
0.6462	Remote Similarity	NPD854	Approved
0.6458	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5578	Approved
0.6454	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD999	Phase 2
0.6434	Remote Similarity	NPD2066	Phase 3
0.6433	Remote Similarity	NPD5030	Phase 2
0.6429	Remote Similarity	NPD1759	Phase 1
0.6429	Remote Similarity	NPD7082	Approved
0.6424	Remote Similarity	NPD2569	Approved
0.6424	Remote Similarity	NPD2567	Approved
0.6423	Remote Similarity	NPD2652	Approved
0.6423	Remote Similarity	NPD2650	Approved
0.6423	Remote Similarity	NPD6010	Discontinued
0.6414	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD7720	Phase 2
0.6403	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4684	Phase 3
0.64	Remote Similarity	NPD4685	Phase 3
0.64	Remote Similarity	NPD4686	Approved
0.6395	Remote Similarity	NPD4955	Approved
0.6395	Remote Similarity	NPD4954	Approved
0.6395	Remote Similarity	NPD5026	Approved
0.6395	Remote Similarity	NPD36	Approved
0.6395	Remote Similarity	NPD5028	Approved
0.6395	Remote Similarity	NPD5034	Approved
0.6387	Remote Similarity	NPD7259	Approved
0.6383	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD1710	Approved
0.6378	Remote Similarity	NPD4094	Approved
0.6377	Remote Similarity	NPD2629	Approved
0.6376	Remote Similarity	NPD7713	Phase 3
0.6375	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.637	Remote Similarity	NPD1756	Approved
0.637	Remote Similarity	NPD1752	Approved
0.6369	Remote Similarity	NPD8165	Discontinued
0.6364	Remote Similarity	NPD8361	Approved
0.6364	Remote Similarity	NPD4807	Approved
0.6364	Remote Similarity	NPD4806	Approved
0.6364	Remote Similarity	NPD8360	Approved
0.6364	Remote Similarity	NPD1237	Approved
0.6364	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5035	Approved
0.6357	Remote Similarity	NPD7610	Discontinued
0.6357	Remote Similarity	NPD2115	Approved
0.6357	Remote Similarity	NPD2117	Pre-registration
0.6357	Remote Similarity	NPD9609	Approved
0.6357	Remote Similarity	NPD9612	Approved
0.6357	Remote Similarity	NPD2116	Approved
0.6357	Remote Similarity	NPD9611	Approved
0.6349	Remote Similarity	NPD752	Approved
0.6349	Remote Similarity	NPD7631	Approved
0.6347	Remote Similarity	NPD7315	Approved
0.6346	Remote Similarity	NPD8323	Discontinued
0.6343	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD2932	Approved
0.6338	Remote Similarity	NPD5306	Approved
0.6338	Remote Similarity	NPD5305	Approved
0.6336	Remote Similarity	NPD5716	Approved
0.6336	Remote Similarity	NPD4119	Approved
0.6336	Remote Similarity	NPD6027	Approved
0.6336	Remote Similarity	NPD4818	Approved
0.6336	Remote Similarity	NPD6024	Approved
0.6336	Remote Similarity	NPD4817	Approved
0.6333	Remote Similarity	NPD8485	Approved
0.6331	Remote Similarity	NPD7508	Discontinued
0.6328	Remote Similarity	NPD2895	Discontinued
0.6324	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD8407	Phase 2
0.6319	Remote Similarity	NPD2584	Suspended
0.6319	Remote Similarity	NPD6624	Discontinued
0.6316	Remote Similarity	NPD5190	Phase 2
0.6316	Remote Similarity	NPD1040	Phase 2
0.6316	Remote Similarity	NPD5048	Discontinued
0.6316	Remote Similarity	NPD2197	Approved
0.6316	Remote Similarity	NPD2192	Approved
0.6312	Remote Similarity	NPD7009	Phase 2
0.6312	Remote Similarity	NPD2617	Discontinued
0.6312	Remote Similarity	NPD998	Approved
0.6312	Remote Similarity	NPD2994	Approved
0.6309	Remote Similarity	NPD4621	Approved
0.6309	Remote Similarity	NPD4619	Approved
0.6299	Remote Similarity	NPD3719	Approved
0.6299	Remote Similarity	NPD4152	Approved
0.6299	Remote Similarity	NPD719	Approved
0.6299	Remote Similarity	NPD3718	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