NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	2.548
LogD:	2.243
LogS:	-3.421
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	4.471
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.477
MDCK Permeability:	3.166022725054063e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.305
Plasma Protein Binding (PPB):	74.93592071533203%
Volume Distribution (VD):	2.294
Pgp-substrate:	7.9376301765441895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.648
CYP1A2-substrate:	0.267
CYP2C19-inhibitor:	0.224
CYP2C19-substrate:	0.514
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.236

ADMET: Excretion

Clearance (CL):	11.174
Half-life (T1/2):	0.194

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.147
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.951
Maximum Recommended Daily Dose:	0.307
Skin Sensitization:	0.549
Carcinogencity:	0.836
Eye Corrosion:	0.9
Eye Irritation:	0.867
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC156485

Natural Product ID:	NPC156485
*Common Name:**	Micheliolide
IUPAC Name:	(3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylidene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
Synonyms:	Micheliolide
Standard InCHIKey:	RDJAFOWISVMOJY-PWNZVWSESA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h11-13,17H,2,4-7H2,1,3H3/t11-,12-,13-,15+/m0/s1
SMILES:	CC1=C2CC[C@@]([C@@H]2[C@@H]2[C@@H](CC1)C(=C)C(=O)O2)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449579
PubChem CID:	442279
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO31577.1	Michelia compressa var. formosana	Varieties	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31577.1	Michelia compressa var. formosana	Varieties	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	4
MIC	1
Others	33

Activity Type	# Activity
Cell Line	3
Individual Protein	2
NON-MOLECULAR	9
Organism	19
Others	5
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	5500.0	nM	PMID[525776]
NPT52	Individual Protein	Pyruvate kinase isozymes M1/M2	Homo sapiens	EC50	=	6.0	nM	PMID[525777]
NPT584	Individual Protein	NACHT, LRR and PYD domains-containing protein 3	Homo sapiens	IC50	=	5900.0	nM	PMID[525778]
NPT1182	Cell Line	J774.A1	Mus musculus	TC50	=	21.9	uM	PMID[525778]
NPT2615	Cell Line	HEK-293T	Homo sapiens	TC50	=	51.7	uM	PMID[525778]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	50.0	ug.mL-1	PMID[525775]
NPT32	Organism	Mus musculus	Mus musculus	Cmax	=	10.71	ug.mL-1	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	Vd	=	533.45	L.kg-1	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	CL	=	287.5	mL.min-1.kg-1	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	T1/2	=	12.66	hr	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	MRT	=	6.34	hr	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	MRT	=	1.49	hr	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	AUC	=	5847.3	ng.hr.mL-1	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	AUC	=	5489.4	ng.hr.mL-1	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	Cmax	=	2.608	ug.mL-1	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	Vd	=	265.27	L.kg-1	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	CL	=	376.5	mL.min-1.kg-1	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	Tmax	=	0.36	hr	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	T1/2	=	7.92	hr	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	MRT	=	8.28	hr	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	MRT	=	7.59	hr	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	AUC	=	6715.2	ng.hr.mL-1	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	AUC	=	6632.3	ng.hr.mL-1	PMID[525776]
NPT32	Organism	Mus musculus	Mus musculus	T1/2	=	2.64	hr	PMID[525776]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CFU	=	0.0	n.a.	PMID[525776]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CFU	=	4.5	n.a.	PMID[525776]
NPT2	Others	Unspecified		Activity	=	1.42	%	PMID[525776]
NPT2	Others	Unspecified		Activity	=	24.2	%	PMID[525776]
NPT2	Others	Unspecified		Activity	=	69.4	%	PMID[525776]
NPT2	Others	Unspecified		Activity	=	0.127	%	PMID[525776]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	FC	=	5.3	n.a.	PMID[525776]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	FC	=	3.2	n.a.	PMID[525776]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.3	%	PMID[525776]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	4.2	%	PMID[525776]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	8.4	%	PMID[525776]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	11.7	%	PMID[525776]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6200.0	nM	PMID[525776]
NPT25490	SINGLE PROTEIN	NACHT, LRR and PYD domains-containing protein 3	Mus musculus	IC50	=	2300.0	nM	PMID[525778]
NPT27	Others	Unspecified		Ratio	=	9.5	n.a.	PMID[525778]

☑ 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 NPC156485 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	191
0.1-0.2	1208
0.2-0.3	5817
0.3-0.4	15605
0.4-0.5	9484
0.5-0.6	6904
0.6-0.7	2805
0.7-0.8	585
0.8-0.85	75
0.85-0.9	18
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9506	High Similarity	NPC67493
0.9136	High Similarity	NPC245665
0.9114	High Similarity	NPC182550
0.9059	High Similarity	NPC37607
0.9059	High Similarity	NPC301969
0.8966	High Similarity	NPC127019
0.8916	High Similarity	NPC235792
0.8875	High Similarity	NPC470239
0.8875	High Similarity	NPC470244
0.8864	High Similarity	NPC170120
0.8864	High Similarity	NPC213698
0.8864	High Similarity	NPC67584
0.8864	High Similarity	NPC52044
0.8824	High Similarity	NPC224652
0.8764	High Similarity	NPC213078
0.8706	High Similarity	NPC201658
0.869	High Similarity	NPC284534
0.869	High Similarity	NPC300082
0.869	High Similarity	NPC204105
0.8667	High Similarity	NPC161493
0.8605	High Similarity	NPC79549
0.8605	High Similarity	NPC91248
0.8571	High Similarity	NPC221615
0.8554	High Similarity	NPC89555
0.8537	High Similarity	NPC302426
0.8537	High Similarity	NPC276356
0.8537	High Similarity	NPC74673
0.8537	High Similarity	NPC69271
0.8523	High Similarity	NPC131209
0.8523	High Similarity	NPC133698
0.8506	High Similarity	NPC215556
0.8481	Intermediate Similarity	NPC143979
0.8481	Intermediate Similarity	NPC320537
0.8471	Intermediate Similarity	NPC165162
0.8434	Intermediate Similarity	NPC10276
0.8434	Intermediate Similarity	NPC35089
0.8409	Intermediate Similarity	NPC216284
0.8409	Intermediate Similarity	NPC129419
0.8395	Intermediate Similarity	NPC470240
0.8395	Intermediate Similarity	NPC65603
0.8395	Intermediate Similarity	NPC53581
0.8395	Intermediate Similarity	NPC476794
0.8395	Intermediate Similarity	NPC103987
0.8387	Intermediate Similarity	NPC150923
0.8375	Intermediate Similarity	NPC138408
0.8375	Intermediate Similarity	NPC193351
0.8375	Intermediate Similarity	NPC226669
0.8372	Intermediate Similarity	NPC107787
0.8372	Intermediate Similarity	NPC56593
0.8372	Intermediate Similarity	NPC236692
0.8372	Intermediate Similarity	NPC309757
0.8353	Intermediate Similarity	NPC165287
0.8353	Intermediate Similarity	NPC115786
0.8333	Intermediate Similarity	NPC470013
0.8333	Intermediate Similarity	NPC198853
0.8333	Intermediate Similarity	NPC470010
0.8333	Intermediate Similarity	NPC323008
0.8333	Intermediate Similarity	NPC477131
0.8333	Intermediate Similarity	NPC262133
0.8315	Intermediate Similarity	NPC155215
0.8295	Intermediate Similarity	NPC212664
0.8295	Intermediate Similarity	NPC268298
0.8295	Intermediate Similarity	NPC155935
0.828	Intermediate Similarity	NPC70865
0.8276	Intermediate Similarity	NPC118601
0.8256	Intermediate Similarity	NPC245434
0.8256	Intermediate Similarity	NPC78089
0.825	Intermediate Similarity	NPC472966
0.825	Intermediate Similarity	NPC469643
0.825	Intermediate Similarity	NPC469641
0.8222	Intermediate Similarity	NPC473273
0.8222	Intermediate Similarity	NPC308656
0.8222	Intermediate Similarity	NPC258216
0.8222	Intermediate Similarity	NPC60386
0.8222	Intermediate Similarity	NPC473263
0.8222	Intermediate Similarity	NPC135776
0.8222	Intermediate Similarity	NPC473234
0.8214	Intermediate Similarity	NPC301477
0.8214	Intermediate Similarity	NPC281949
0.8214	Intermediate Similarity	NPC25684
0.8202	Intermediate Similarity	NPC297474
0.8202	Intermediate Similarity	NPC35809
0.8202	Intermediate Similarity	NPC54065
0.8193	Intermediate Similarity	NPC617
0.8182	Intermediate Similarity	NPC217983
0.8182	Intermediate Similarity	NPC207114
0.8182	Intermediate Similarity	NPC178875
0.8171	Intermediate Similarity	NPC195785
0.8171	Intermediate Similarity	NPC208223
0.8171	Intermediate Similarity	NPC15975
0.8161	Intermediate Similarity	NPC187661
0.814	Intermediate Similarity	NPC194859
0.814	Intermediate Similarity	NPC114979
0.814	Intermediate Similarity	NPC191476
0.814	Intermediate Similarity	NPC224386
0.8132	Intermediate Similarity	NPC167219
0.8111	Intermediate Similarity	NPC293001
0.8111	Intermediate Similarity	NPC35959
0.8111	Intermediate Similarity	NPC29821
0.8111	Intermediate Similarity	NPC261607
0.8111	Intermediate Similarity	NPC184063
0.8111	Intermediate Similarity	NPC63193
0.8111	Intermediate Similarity	NPC133888
0.8111	Intermediate Similarity	NPC57304
0.8111	Intermediate Similarity	NPC111114
0.8111	Intermediate Similarity	NPC300312
0.8111	Intermediate Similarity	NPC171360
0.8095	Intermediate Similarity	NPC73052
0.8095	Intermediate Similarity	NPC156658
0.8095	Intermediate Similarity	NPC258965
0.8095	Intermediate Similarity	NPC293418
0.8095	Intermediate Similarity	NPC6823
0.8095	Intermediate Similarity	NPC290508
0.809	Intermediate Similarity	NPC12872
0.809	Intermediate Similarity	NPC168679
0.809	Intermediate Similarity	NPC4986
0.8072	Intermediate Similarity	NPC267231
0.8068	Intermediate Similarity	NPC237540
0.8068	Intermediate Similarity	NPC190753
0.8065	Intermediate Similarity	NPC170143
0.8065	Intermediate Similarity	NPC213947
0.8065	Intermediate Similarity	NPC108475
0.8049	Intermediate Similarity	NPC235906
0.8046	Intermediate Similarity	NPC255307
0.8043	Intermediate Similarity	NPC163228
0.8043	Intermediate Similarity	NPC472873
0.8043	Intermediate Similarity	NPC304886
0.8043	Intermediate Similarity	NPC476053
0.8043	Intermediate Similarity	NPC224689
0.8023	Intermediate Similarity	NPC250315
0.8023	Intermediate Similarity	NPC39588
0.8023	Intermediate Similarity	NPC215294
0.8022	Intermediate Similarity	NPC153590
0.8021	Intermediate Similarity	NPC124881
0.8	Intermediate Similarity	NPC19087
0.8	Intermediate Similarity	NPC470241
0.8	Intermediate Similarity	NPC325031
0.8	Intermediate Similarity	NPC255580
0.8	Intermediate Similarity	NPC39411
0.8	Intermediate Similarity	NPC141810
0.7976	Intermediate Similarity	NPC264227
0.7976	Intermediate Similarity	NPC89128
0.7976	Intermediate Similarity	NPC63649
0.7976	Intermediate Similarity	NPC472965
0.7976	Intermediate Similarity	NPC98557
0.7976	Intermediate Similarity	NPC167881
0.7975	Intermediate Similarity	NPC5714
0.7957	Intermediate Similarity	NPC18019
0.7957	Intermediate Similarity	NPC24956
0.7955	Intermediate Similarity	NPC150755
0.7955	Intermediate Similarity	NPC305475
0.7955	Intermediate Similarity	NPC475461
0.7952	Intermediate Similarity	NPC320630
0.7952	Intermediate Similarity	NPC7563
0.7952	Intermediate Similarity	NPC116177
0.7935	Intermediate Similarity	NPC96541
0.7931	Intermediate Similarity	NPC141193
0.7931	Intermediate Similarity	NPC96259
0.7931	Intermediate Similarity	NPC476804
0.7927	Intermediate Similarity	NPC155587
0.7912	Intermediate Similarity	NPC475925
0.7907	Intermediate Similarity	NPC229825
0.7907	Intermediate Similarity	NPC246076
0.7889	Intermediate Similarity	NPC32922
0.7889	Intermediate Similarity	NPC38392
0.7889	Intermediate Similarity	NPC472872
0.7882	Intermediate Similarity	NPC51507
0.7875	Intermediate Similarity	NPC472955
0.7872	Intermediate Similarity	NPC471150
0.7872	Intermediate Similarity	NPC311904
0.7865	Intermediate Similarity	NPC160138
0.7865	Intermediate Similarity	NPC24728
0.7865	Intermediate Similarity	NPC270270
0.7857	Intermediate Similarity	NPC196653
0.7857	Intermediate Similarity	NPC299235
0.7857	Intermediate Similarity	NPC108816
0.7857	Intermediate Similarity	NPC472960
0.7857	Intermediate Similarity	NPC93763
0.7857	Intermediate Similarity	NPC471465
0.7849	Intermediate Similarity	NPC275960
0.7849	Intermediate Similarity	NPC90121
0.7849	Intermediate Similarity	NPC469873
0.7849	Intermediate Similarity	NPC193645
0.7849	Intermediate Similarity	NPC48803
0.7841	Intermediate Similarity	NPC161957
0.7841	Intermediate Similarity	NPC21471
0.7841	Intermediate Similarity	NPC33570
0.7826	Intermediate Similarity	NPC200237
0.7816	Intermediate Similarity	NPC473390
0.7816	Intermediate Similarity	NPC131669
0.7816	Intermediate Similarity	NPC128246
0.7816	Intermediate Similarity	NPC111409
0.7816	Intermediate Similarity	NPC54468
0.7802	Intermediate Similarity	NPC469368
0.7791	Intermediate Similarity	NPC59994
0.7791	Intermediate Similarity	NPC126248
0.7791	Intermediate Similarity	NPC78677
0.7791	Intermediate Similarity	NPC52861
0.7791	Intermediate Similarity	NPC24417
0.7789	Intermediate Similarity	NPC45125

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 NPC156485 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1887
0.2-0.3	3986
0.3-0.4	2161
0.4-0.5	552
0.5-0.6	293
0.6-0.7	61
0.7-0.8	17
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
0.809	Intermediate Similarity	NPD1695	Approved
0.7849	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5785	Approved
0.7416	Intermediate Similarity	NPD5362	Discontinued
0.7386	Intermediate Similarity	NPD5369	Approved
0.7253	Intermediate Similarity	NPD5363	Approved
0.7253	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6435	Approved
0.7111	Intermediate Similarity	NPD4270	Approved
0.7111	Intermediate Similarity	NPD4269	Approved
0.7079	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4822	Approved
0.7079	Intermediate Similarity	NPD4821	Approved
0.7079	Intermediate Similarity	NPD4820	Approved
0.7079	Intermediate Similarity	NPD4819	Approved
0.7065	Intermediate Similarity	NPD1694	Approved
0.7048	Intermediate Similarity	NPD6371	Approved
0.7033	Intermediate Similarity	NPD7154	Phase 3
0.6989	Remote Similarity	NPD4249	Approved
0.6989	Remote Similarity	NPD5786	Approved
0.6916	Remote Similarity	NPD6053	Discontinued
0.6915	Remote Similarity	NPD4251	Approved
0.6915	Remote Similarity	NPD4250	Approved
0.6889	Remote Similarity	NPD4252	Approved
0.6889	Remote Similarity	NPD5368	Approved
0.6854	Remote Similarity	NPD4271	Approved
0.6854	Remote Similarity	NPD4268	Approved
0.6848	Remote Similarity	NPD5331	Approved
0.6848	Remote Similarity	NPD5332	Approved
0.6813	Remote Similarity	NPD4790	Discontinued
0.6768	Remote Similarity	NPD5695	Phase 3
0.6739	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6399	Phase 3
0.6733	Remote Similarity	NPD5696	Approved
0.6733	Remote Similarity	NPD4225	Approved
0.6701	Remote Similarity	NPD6698	Approved
0.6701	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5282	Discontinued
0.6634	Remote Similarity	NPD6084	Phase 2
0.6634	Remote Similarity	NPD6083	Phase 2
0.6632	Remote Similarity	NPD5330	Approved
0.6632	Remote Similarity	NPD6684	Approved
0.6632	Remote Similarity	NPD7521	Approved
0.6632	Remote Similarity	NPD7334	Approved
0.6632	Remote Similarity	NPD7146	Approved
0.6632	Remote Similarity	NPD6409	Approved
0.6531	Remote Similarity	NPD5207	Approved
0.6518	Remote Similarity	NPD7115	Discovery
0.6495	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5693	Phase 1
0.6449	Remote Similarity	NPD5697	Approved
0.6436	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6101	Approved
0.6421	Remote Similarity	NPD3133	Approved
0.6421	Remote Similarity	NPD3665	Phase 1
0.6421	Remote Similarity	NPD3666	Approved
0.6408	Remote Similarity	NPD7638	Approved
0.64	Remote Similarity	NPD5778	Approved
0.64	Remote Similarity	NPD5779	Approved
0.6389	Remote Similarity	NPD7320	Approved
0.6389	Remote Similarity	NPD6899	Approved
0.6389	Remote Similarity	NPD6881	Approved
0.6383	Remote Similarity	NPD5209	Approved
0.6383	Remote Similarity	NPD3667	Approved
0.6364	Remote Similarity	NPD6650	Approved
0.6364	Remote Similarity	NPD6649	Approved
0.6364	Remote Similarity	NPD7838	Discovery
0.6355	Remote Similarity	NPD5739	Approved
0.6355	Remote Similarity	NPD7128	Approved
0.6355	Remote Similarity	NPD6675	Approved
0.6355	Remote Similarity	NPD6008	Approved
0.6355	Remote Similarity	NPD6402	Approved
0.6346	Remote Similarity	NPD7639	Approved
0.6346	Remote Similarity	NPD7640	Approved
0.6337	Remote Similarity	NPD6001	Approved
0.633	Remote Similarity	NPD6373	Approved
0.633	Remote Similarity	NPD6012	Approved
0.633	Remote Similarity	NPD6372	Approved
0.633	Remote Similarity	NPD6013	Approved
0.633	Remote Similarity	NPD6014	Approved
0.63	Remote Similarity	NPD5281	Approved
0.63	Remote Similarity	NPD5284	Approved
0.63	Remote Similarity	NPD6411	Approved
0.6296	Remote Similarity	NPD5701	Approved
0.6289	Remote Similarity	NPD3618	Phase 1
0.6275	Remote Similarity	NPD5210	Approved
0.6275	Remote Similarity	NPD4629	Approved
0.6273	Remote Similarity	NPD7102	Approved
0.6273	Remote Similarity	NPD7290	Approved
0.6273	Remote Similarity	NPD6883	Approved
0.6263	Remote Similarity	NPD4753	Phase 2
0.625	Remote Similarity	NPD4786	Approved
0.6239	Remote Similarity	NPD6011	Approved
0.6239	Remote Similarity	NPD6686	Approved
0.622	Remote Similarity	NPD3198	Approved
0.6216	Remote Similarity	NPD6869	Approved
0.6216	Remote Similarity	NPD6847	Approved
0.6216	Remote Similarity	NPD6617	Approved
0.6216	Remote Similarity	NPD8130	Phase 1
0.6216	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4221	Approved
0.6211	Remote Similarity	NPD4223	Phase 3
0.6162	Remote Similarity	NPD6672	Approved
0.6162	Remote Similarity	NPD5737	Approved
0.6162	Remote Similarity	NPD5208	Approved
0.6161	Remote Similarity	NPD8297	Approved
0.6161	Remote Similarity	NPD6882	Approved
0.6154	Remote Similarity	NPD8039	Approved
0.6146	Remote Similarity	NPD4788	Approved
0.6139	Remote Similarity	NPD7983	Approved
0.6139	Remote Similarity	NPD8035	Phase 2
0.6139	Remote Similarity	NPD7637	Suspended
0.6139	Remote Similarity	NPD8034	Phase 2
0.6122	Remote Similarity	NPD5690	Phase 2
0.6122	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6098	Approved
0.6122	Remote Similarity	NPD5279	Phase 3
0.61	Remote Similarity	NPD6051	Approved
0.61	Remote Similarity	NPD5370	Suspended
0.61	Remote Similarity	NPD6080	Approved
0.61	Remote Similarity	NPD6673	Approved
0.61	Remote Similarity	NPD6904	Approved
0.6095	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4197	Approved
0.6078	Remote Similarity	NPD4202	Approved
0.6075	Remote Similarity	NPD5211	Phase 2
0.6047	Remote Similarity	NPD7341	Phase 2
0.604	Remote Similarity	NPD5692	Phase 3
0.6038	Remote Similarity	NPD5285	Approved
0.6038	Remote Similarity	NPD4696	Approved
0.6038	Remote Similarity	NPD5286	Approved
0.602	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5329	Approved
0.6019	Remote Similarity	NPD7748	Approved
0.6017	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD4518	Approved
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD4755	Approved
0.5982	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5344	Discontinued
0.598	Remote Similarity	NPD5694	Approved
0.598	Remote Similarity	NPD6079	Approved
0.598	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6050	Approved
0.5979	Remote Similarity	NPD6695	Phase 3
0.5977	Remote Similarity	NPD7331	Phase 2
0.5963	Remote Similarity	NPD5141	Approved
0.596	Remote Similarity	NPD4688	Approved
0.596	Remote Similarity	NPD4690	Approved
0.596	Remote Similarity	NPD5280	Approved
0.596	Remote Similarity	NPD4138	Approved
0.596	Remote Similarity	NPD4694	Approved
0.596	Remote Similarity	NPD4689	Approved
0.596	Remote Similarity	NPD4693	Phase 3
0.596	Remote Similarity	NPD5205	Approved
0.595	Remote Similarity	NPD7507	Approved
0.5941	Remote Similarity	NPD5328	Approved
0.5929	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5226	Approved
0.5926	Remote Similarity	NPD7632	Discontinued
0.5926	Remote Similarity	NPD5224	Approved
0.5926	Remote Similarity	NPD5225	Approved
0.5926	Remote Similarity	NPD4633	Approved
0.5918	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD3668	Phase 3
0.5918	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD7839	Suspended
0.5893	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4700	Approved
0.5888	Remote Similarity	NPD6648	Approved
0.5872	Remote Similarity	NPD5175	Approved
0.5872	Remote Similarity	NPD6052	Approved
0.5872	Remote Similarity	NPD5174	Approved
0.587	Remote Similarity	NPD6926	Approved
0.587	Remote Similarity	NPD6924	Approved
0.5868	Remote Similarity	NPD7492	Approved
0.5856	Remote Similarity	NPD6412	Phase 2
0.5851	Remote Similarity	NPD4756	Discovery
0.5847	Remote Similarity	NPD7100	Approved
0.5847	Remote Similarity	NPD7101	Approved
0.5841	Remote Similarity	NPD6420	Discontinued
0.5833	Remote Similarity	NPD6931	Approved
0.5833	Remote Similarity	NPD6930	Phase 2
0.5833	Remote Similarity	NPD4695	Discontinued
0.5833	Remote Similarity	NPD5223	Approved
0.5826	Remote Similarity	NPD4632	Approved
0.5825	Remote Similarity	NPD7515	Phase 2
0.582	Remote Similarity	NPD6616	Approved
0.5812	Remote Similarity	NPD6317	Approved
0.5806	Remote Similarity	NPD3702	Approved
0.5806	Remote Similarity	NPD7319	Approved
0.58	Remote Similarity	NPD6422	Discontinued
0.5798	Remote Similarity	NPD6319	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