NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.14
Volume:	260.839
LogP:	2.687
LogD:	2.48
LogS:	-2.011
# Rotatable Bonds:	0
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.618
Synthetic Accessibility Score:	3.864
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.784
MDCK Permeability:	1.9072596842306666e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.048
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.126
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.253
Plasma Protein Binding (PPB):	79.2555923461914%
Volume Distribution (VD):	1.178
Pgp-substrate:	21.993942260742188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.179
CYP1A2-substrate:	0.835
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.365
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.141
CYP2D6-substrate:	0.62
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.166

ADMET: Excretion

Clearance (CL):	15.323
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.597
Rat Oral Acute Toxicity:	0.374
Maximum Recommended Daily Dose:	0.599
Skin Sensitization:	0.936
Carcinogencity:	0.5
Eye Corrosion:	0.031
Eye Irritation:	0.899
Respiratory Toxicity:	0.521

Download Data

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

Natural Product: NPC28887

Natural Product ID:	NPC28887
*Common Name:**	(4S,5R,6R,11S)-4-Hydroxy-11-Methyl-4,5,6,7,8,9,10,11-Octahydro-1H-Benzo[D]Oxecine-1,12-Dione
IUPAC Name:	(4S,8aR,12S,12aR)-12-hydroxy-4-methyl-4,5,6,7,8,8a,12,12a-octahydro-1H-3-benzoxecine-2,9-dione
Synonyms:	SCH-642305
Standard InCHIKey:	WTQWDNIIFGEBSZ-WGBDABJCSA-N
Standard InCHI:	InChI=1S/C14H20O4/c1-9-4-2-3-5-10-11(8-14(17)18-9)13(16)7-6-12(10)15/h6-7,9-11,13,16H,2-5,8H2,1H3/t9-,10+,11+,13-/m0/s1
SMILES:	C[C@H]1CCCC[C@@H]2[C@@H](CC(=O)O1)[C@H](C=CC2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453428
PubChem CID:	637324
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001796] Oxocins

*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
NPO21037	Penicillium verrucosum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695789]
NPO21037	Penicillium verrucosum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
EC50	1
IC50	2
MIC	1
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2223	Individual Protein	Mobilization protein A	Escherichia coli	EC50	=	70000.0	nM	PMID[570492]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	20.0	nM	PMID[570493]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	20.0	nM	PMID[570493]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	40.0	ug.mL-1	PMID[570492]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	Activity	=	100.0	%	PMID[570493]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	Activity	=	38.0	%	PMID[570493]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	0.0	%	PMID[570493]

☑ 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 NPC28887 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	194
0.1-0.2	1207
0.2-0.3	5597
0.3-0.4	12742
0.4-0.5	12806
0.5-0.6	6796
0.6-0.7	3041
0.7-0.8	312
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8193	Intermediate Similarity	NPC192006
0.8046	Intermediate Similarity	NPC96259
0.8046	Intermediate Similarity	NPC141193
0.7978	Intermediate Similarity	NPC237540
0.7955	Intermediate Similarity	NPC125290
0.7955	Intermediate Similarity	NPC261380
0.7917	Intermediate Similarity	NPC115862
0.7907	Intermediate Similarity	NPC470241
0.7865	Intermediate Similarity	NPC475461
0.7865	Intermediate Similarity	NPC305475
0.7841	Intermediate Similarity	NPC230527
0.7841	Intermediate Similarity	NPC191476
0.7841	Intermediate Similarity	NPC476804
0.7841	Intermediate Similarity	NPC472326
0.7841	Intermediate Similarity	NPC472957
0.7841	Intermediate Similarity	NPC7927
0.7841	Intermediate Similarity	NPC472958
0.7841	Intermediate Similarity	NPC114979
0.7816	Intermediate Similarity	NPC85772
0.7816	Intermediate Similarity	NPC279186
0.7802	Intermediate Similarity	NPC268298
0.7802	Intermediate Similarity	NPC212598
0.7791	Intermediate Similarity	NPC271104
0.7753	Intermediate Similarity	NPC255307
0.7753	Intermediate Similarity	NPC165162
0.7742	Intermediate Similarity	NPC475302
0.7742	Intermediate Similarity	NPC476416
0.7738	Intermediate Similarity	NPC279537
0.7732	Intermediate Similarity	NPC224720
0.7732	Intermediate Similarity	NPC476223
0.7732	Intermediate Similarity	NPC476240
0.7727	Intermediate Similarity	NPC1761
0.7727	Intermediate Similarity	NPC40746
0.7727	Intermediate Similarity	NPC169575
0.7727	Intermediate Similarity	NPC52609
0.7717	Intermediate Similarity	NPC129419
0.7717	Intermediate Similarity	NPC265856
0.7717	Intermediate Similarity	NPC166554
0.7701	Intermediate Similarity	NPC24417
0.7701	Intermediate Similarity	NPC52861
0.7692	Intermediate Similarity	NPC476805
0.7683	Intermediate Similarity	NPC67076
0.7683	Intermediate Similarity	NPC319163
0.7674	Intermediate Similarity	NPC89128
0.767	Intermediate Similarity	NPC66108
0.7667	Intermediate Similarity	NPC234038
0.764	Intermediate Similarity	NPC70424
0.764	Intermediate Similarity	NPC243618
0.7634	Intermediate Similarity	NPC111114
0.7634	Intermediate Similarity	NPC261607
0.7634	Intermediate Similarity	NPC300312
0.7634	Intermediate Similarity	NPC252433
0.7629	Intermediate Similarity	NPC476274
0.7614	Intermediate Similarity	NPC229825
0.7614	Intermediate Similarity	NPC173609
0.7609	Intermediate Similarity	NPC117405
0.7609	Intermediate Similarity	NPC52198
0.759	Intermediate Similarity	NPC275098
0.7558	Intermediate Similarity	NPC471465
0.7558	Intermediate Similarity	NPC231739
0.7558	Intermediate Similarity	NPC475994
0.7558	Intermediate Similarity	NPC196653
0.7558	Intermediate Similarity	NPC93763
0.7558	Intermediate Similarity	NPC108816
0.7558	Intermediate Similarity	NPC128276
0.7556	Intermediate Similarity	NPC470755
0.7556	Intermediate Similarity	NPC476426
0.7553	Intermediate Similarity	NPC288240
0.7553	Intermediate Similarity	NPC295204
0.7553	Intermediate Similarity	NPC162205
0.7553	Intermediate Similarity	NPC476049
0.7553	Intermediate Similarity	NPC273579
0.7529	Intermediate Similarity	NPC61863
0.7529	Intermediate Similarity	NPC12740
0.7529	Intermediate Similarity	NPC110461
0.7528	Intermediate Similarity	NPC59097
0.7528	Intermediate Similarity	NPC131669
0.7528	Intermediate Similarity	NPC473390
0.7527	Intermediate Similarity	NPC471399
0.7527	Intermediate Similarity	NPC473448
0.7527	Intermediate Similarity	NPC144133
0.7527	Intermediate Similarity	NPC469368
0.7527	Intermediate Similarity	NPC179394
0.7527	Intermediate Similarity	NPC475855
0.7526	Intermediate Similarity	NPC141191
0.75	Intermediate Similarity	NPC87189
0.75	Intermediate Similarity	NPC228415
0.75	Intermediate Similarity	NPC325031
0.75	Intermediate Similarity	NPC185553
0.75	Intermediate Similarity	NPC118911
0.75	Intermediate Similarity	NPC47031
0.75	Intermediate Similarity	NPC476803
0.75	Intermediate Similarity	NPC184065
0.75	Intermediate Similarity	NPC136879
0.7474	Intermediate Similarity	NPC476415
0.7474	Intermediate Similarity	NPC475572
0.7473	Intermediate Similarity	NPC116575
0.7473	Intermediate Similarity	NPC316426
0.7473	Intermediate Similarity	NPC150755
0.7473	Intermediate Similarity	NPC315395
0.7471	Intermediate Similarity	NPC167881
0.7471	Intermediate Similarity	NPC469617
0.7471	Intermediate Similarity	NPC19900
0.7471	Intermediate Similarity	NPC98557
0.7471	Intermediate Similarity	NPC113363
0.7449	Intermediate Similarity	NPC287833
0.7444	Intermediate Similarity	NPC149869
0.7444	Intermediate Similarity	NPC165287
0.7444	Intermediate Similarity	NPC158756
0.7444	Intermediate Similarity	NPC219966
0.7444	Intermediate Similarity	NPC196487
0.7444	Intermediate Similarity	NPC295799
0.7444	Intermediate Similarity	NPC14575
0.7442	Intermediate Similarity	NPC471061
0.7442	Intermediate Similarity	NPC187568
0.7442	Intermediate Similarity	NPC320630
0.7442	Intermediate Similarity	NPC41780
0.7442	Intermediate Similarity	NPC116177
0.7442	Intermediate Similarity	NPC107668
0.7442	Intermediate Similarity	NPC7563
0.7442	Intermediate Similarity	NPC57744
0.7439	Intermediate Similarity	NPC199557
0.7439	Intermediate Similarity	NPC143396
0.7423	Intermediate Similarity	NPC169205
0.7423	Intermediate Similarity	NPC40812
0.7423	Intermediate Similarity	NPC170131
0.7423	Intermediate Similarity	NPC474343
0.7423	Intermediate Similarity	NPC91695
0.7423	Intermediate Similarity	NPC20066
0.7423	Intermediate Similarity	NPC70145
0.7419	Intermediate Similarity	NPC115179
0.7419	Intermediate Similarity	NPC206001
0.7419	Intermediate Similarity	NPC5509
0.7419	Intermediate Similarity	NPC474032
0.7419	Intermediate Similarity	NPC295312
0.7419	Intermediate Similarity	NPC106040
0.7419	Intermediate Similarity	NPC218927
0.7416	Intermediate Similarity	NPC7414
0.7416	Intermediate Similarity	NPC474252
0.7416	Intermediate Similarity	NPC38796
0.7416	Intermediate Similarity	NPC158411
0.7416	Intermediate Similarity	NPC89555
0.7396	Intermediate Similarity	NPC272050
0.7396	Intermediate Similarity	NPC48803
0.7396	Intermediate Similarity	NPC90121
0.7396	Intermediate Similarity	NPC275960
0.7396	Intermediate Similarity	NPC193645
0.7396	Intermediate Similarity	NPC304886
0.7391	Intermediate Similarity	NPC471738
0.7391	Intermediate Similarity	NPC476409
0.7391	Intermediate Similarity	NPC312561
0.7386	Intermediate Similarity	NPC470946
0.7386	Intermediate Similarity	NPC470945
0.7386	Intermediate Similarity	NPC470947
0.7381	Intermediate Similarity	NPC186042
0.7381	Intermediate Similarity	NPC472956
0.7374	Intermediate Similarity	NPC81530
0.7368	Intermediate Similarity	NPC228451
0.7368	Intermediate Similarity	NPC475838
0.7368	Intermediate Similarity	NPC125674
0.7363	Intermediate Similarity	NPC52628
0.7356	Intermediate Similarity	NPC62336
0.7356	Intermediate Similarity	NPC267231
0.7347	Intermediate Similarity	NPC300584
0.7347	Intermediate Similarity	NPC222011
0.7347	Intermediate Similarity	NPC23364
0.7347	Intermediate Similarity	NPC187761
0.7347	Intermediate Similarity	NPC308567
0.7347	Intermediate Similarity	NPC255592
0.7347	Intermediate Similarity	NPC478056
0.7347	Intermediate Similarity	NPC83895
0.7347	Intermediate Similarity	NPC261377
0.7347	Intermediate Similarity	NPC316598
0.734	Intermediate Similarity	NPC232426
0.734	Intermediate Similarity	NPC473455
0.734	Intermediate Similarity	NPC77337
0.734	Intermediate Similarity	NPC145666
0.734	Intermediate Similarity	NPC476369
0.734	Intermediate Similarity	NPC106510
0.734	Intermediate Similarity	NPC214844
0.734	Intermediate Similarity	NPC71533
0.734	Intermediate Similarity	NPC471818
0.734	Intermediate Similarity	NPC476437
0.734	Intermediate Similarity	NPC281942
0.7333	Intermediate Similarity	NPC474703
0.7333	Intermediate Similarity	NPC16488
0.7333	Intermediate Similarity	NPC477786
0.7333	Intermediate Similarity	NPC477785
0.7333	Intermediate Similarity	NPC477784
0.7326	Intermediate Similarity	NPC472967
0.7326	Intermediate Similarity	NPC266119
0.7326	Intermediate Similarity	NPC266159
0.732	Intermediate Similarity	NPC456
0.732	Intermediate Similarity	NPC202833
0.732	Intermediate Similarity	NPC472941
0.7317	Intermediate Similarity	NPC476629
0.7317	Intermediate Similarity	NPC476614
0.7312	Intermediate Similarity	NPC249889
0.7312	Intermediate Similarity	NPC473715
0.7312	Intermediate Similarity	NPC477302

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 NPC28887 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1831
0.2-0.3	3828
0.3-0.4	2240
0.4-0.5	715
0.5-0.6	286
0.6-0.7	61
0.7-0.8	10
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
0.7753	Intermediate Similarity	NPD5363	Approved
0.7527	Intermediate Similarity	NPD5785	Approved
0.7473	Intermediate Similarity	NPD5786	Approved
0.7416	Intermediate Similarity	NPD6435	Approved
0.7416	Intermediate Similarity	NPD4270	Approved
0.7416	Intermediate Similarity	NPD4269	Approved
0.7396	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4252	Approved
0.7191	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5368	Approved
0.7188	Intermediate Similarity	NPD5779	Approved
0.7188	Intermediate Similarity	NPD5778	Approved
0.7174	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD5362	Discontinued
0.7143	Intermediate Similarity	NPD7154	Phase 3
0.7111	Intermediate Similarity	NPD5369	Approved
0.7	Intermediate Similarity	NPD4821	Approved
0.7	Intermediate Similarity	NPD4819	Approved
0.7	Intermediate Similarity	NPD4822	Approved
0.7	Intermediate Similarity	NPD4820	Approved
0.6979	Remote Similarity	NPD6698	Approved
0.6979	Remote Similarity	NPD46	Approved
0.6966	Remote Similarity	NPD4271	Approved
0.6966	Remote Similarity	NPD4268	Approved
0.6907	Remote Similarity	NPD7983	Approved
0.6875	Remote Similarity	NPD6101	Approved
0.6875	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4756	Discovery
0.6737	Remote Similarity	NPD4249	Approved
0.6735	Remote Similarity	NPD6411	Approved
0.6733	Remote Similarity	NPD7902	Approved
0.6698	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD7331	Phase 2
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD4251	Approved
0.6636	Remote Similarity	NPD6881	Approved
0.6636	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD6899	Approved
0.6634	Remote Similarity	NPD7839	Suspended
0.6632	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6650	Approved
0.6606	Remote Similarity	NPD6649	Approved
0.66	Remote Similarity	NPD7748	Approved
0.6596	Remote Similarity	NPD5332	Approved
0.6596	Remote Similarity	NPD5331	Approved
0.6596	Remote Similarity	NPD6110	Phase 1
0.6574	Remote Similarity	NPD6013	Approved
0.6574	Remote Similarity	NPD6012	Approved
0.6574	Remote Similarity	NPD6014	Approved
0.6566	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7515	Phase 2
0.6559	Remote Similarity	NPD4790	Discontinued
0.6535	Remote Similarity	NPD4629	Approved
0.6535	Remote Similarity	NPD5210	Approved
0.6531	Remote Similarity	NPD5370	Suspended
0.6514	Remote Similarity	NPD6883	Approved
0.6514	Remote Similarity	NPD7290	Approved
0.6514	Remote Similarity	NPD6371	Approved
0.6514	Remote Similarity	NPD7102	Approved
0.6505	Remote Similarity	NPD4225	Approved
0.6489	Remote Similarity	NPD5209	Approved
0.6476	Remote Similarity	NPD5211	Phase 2
0.6465	Remote Similarity	NPD7838	Discovery
0.646	Remote Similarity	NPD7115	Discovery
0.6458	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6847	Approved
0.6455	Remote Similarity	NPD6869	Approved
0.6455	Remote Similarity	NPD6617	Approved
0.6455	Remote Similarity	NPD8130	Phase 1
0.6449	Remote Similarity	NPD6402	Approved
0.6449	Remote Similarity	NPD6675	Approved
0.6449	Remote Similarity	NPD7128	Approved
0.6449	Remote Similarity	NPD5739	Approved
0.6444	Remote Similarity	NPD8039	Approved
0.6436	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5282	Discontinued
0.6436	Remote Similarity	NPD7900	Approved
0.6422	Remote Similarity	NPD6372	Approved
0.6422	Remote Similarity	NPD6373	Approved
0.6415	Remote Similarity	NPD6647	Phase 2
0.6408	Remote Similarity	NPD6084	Phase 2
0.6408	Remote Similarity	NPD6083	Phase 2
0.64	Remote Similarity	NPD6079	Approved
0.64	Remote Similarity	NPD5281	Approved
0.64	Remote Similarity	NPD5284	Approved
0.6396	Remote Similarity	NPD6882	Approved
0.6396	Remote Similarity	NPD8297	Approved
0.6392	Remote Similarity	NPD3618	Phase 1
0.6392	Remote Similarity	NPD7521	Approved
0.6392	Remote Similarity	NPD7146	Approved
0.6392	Remote Similarity	NPD6409	Approved
0.6392	Remote Similarity	NPD7334	Approved
0.6392	Remote Similarity	NPD6684	Approved
0.6392	Remote Similarity	NPD5330	Approved
0.6389	Remote Similarity	NPD5701	Approved
0.6386	Remote Similarity	NPD368	Approved
0.6373	Remote Similarity	NPD5695	Phase 3
0.6355	Remote Similarity	NPD5141	Approved
0.6354	Remote Similarity	NPD3133	Approved
0.6354	Remote Similarity	NPD3665	Phase 1
0.6354	Remote Similarity	NPD3666	Approved
0.6353	Remote Similarity	NPD7341	Phase 2
0.633	Remote Similarity	NPD6686	Approved
0.633	Remote Similarity	NPD7320	Approved
0.6327	Remote Similarity	NPD3573	Approved
0.6311	Remote Similarity	NPD5222	Approved
0.6311	Remote Similarity	NPD5221	Approved
0.6311	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD1696	Phase 3
0.6286	Remote Similarity	NPD4696	Approved
0.6286	Remote Similarity	NPD7639	Approved
0.6286	Remote Similarity	NPD7640	Approved
0.6286	Remote Similarity	NPD5286	Approved
0.6286	Remote Similarity	NPD5285	Approved
0.6277	Remote Similarity	NPD4695	Discontinued
0.6265	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6672	Approved
0.6263	Remote Similarity	NPD6903	Approved
0.6263	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD5173	Approved
0.625	Remote Similarity	NPD6053	Discontinued
0.6239	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7637	Suspended
0.6235	Remote Similarity	NPD3197	Phase 1
0.6226	Remote Similarity	NPD5223	Approved
0.6226	Remote Similarity	NPD5344	Discontinued
0.6224	Remote Similarity	NPD4519	Discontinued
0.6224	Remote Similarity	NPD4623	Approved
0.6224	Remote Similarity	NPD5279	Phase 3
0.6207	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.62	Remote Similarity	NPD1695	Approved
0.62	Remote Similarity	NPD5328	Approved
0.6195	Remote Similarity	NPD4632	Approved
0.619	Remote Similarity	NPD7638	Approved
0.6186	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6317	Approved
0.6168	Remote Similarity	NPD5226	Approved
0.6168	Remote Similarity	NPD4633	Approved
0.6168	Remote Similarity	NPD5225	Approved
0.6168	Remote Similarity	NPD5224	Approved
0.6163	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7614	Phase 1
0.6154	Remote Similarity	NPD4697	Phase 3
0.6146	Remote Similarity	NPD3667	Approved
0.6121	Remote Similarity	NPD6314	Approved
0.6121	Remote Similarity	NPD6313	Approved
0.6121	Remote Similarity	NPD6335	Approved
0.6118	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5174	Approved
0.6111	Remote Similarity	NPD5175	Approved
0.6105	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4755	Approved
0.6092	Remote Similarity	NPD3704	Approved
0.6087	Remote Similarity	NPD6274	Approved
0.6087	Remote Similarity	NPD6868	Approved
0.6068	Remote Similarity	NPD7100	Approved
0.6068	Remote Similarity	NPD7101	Approved
0.6061	Remote Similarity	NPD6422	Discontinued
0.6048	Remote Similarity	NPD7260	Phase 2
0.604	Remote Similarity	NPD4753	Phase 2
0.6034	Remote Similarity	NPD6009	Approved
0.602	Remote Similarity	NPD4786	Approved
0.6019	Remote Similarity	NPD4202	Approved
0.6018	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD3172	Approved
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD7732	Phase 3
0.5983	Remote Similarity	NPD7641	Discontinued
0.5981	Remote Similarity	NPD6648	Approved
0.5981	Remote Similarity	NPD4700	Approved
0.598	Remote Similarity	NPD5207	Approved
0.5966	Remote Similarity	NPD5983	Phase 2
0.5966	Remote Similarity	NPD8513	Phase 3
0.5966	Remote Similarity	NPD8517	Approved
0.5966	Remote Similarity	NPD8516	Approved
0.5966	Remote Similarity	NPD8515	Approved
0.5962	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6412	Phase 2
0.5926	Remote Similarity	NPD3196	Approved
0.5926	Remote Similarity	NPD4266	Approved
0.5926	Remote Similarity	NPD3194	Approved
0.5926	Remote Similarity	NPD3195	Phase 2
0.5922	Remote Similarity	NPD5694	Approved
0.5922	Remote Similarity	NPD5693	Phase 1
0.5909	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.59	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5690	Phase 2
0.5893	Remote Similarity	NPD4730	Approved
0.5893	Remote Similarity	NPD4729	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