NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	258.152
LogP:	3.255
LogD:	2.63
LogS:	-3.186
# Rotatable Bonds:	0
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.764
Synthetic Accessibility Score:	4.342
Fsp3:	0.533
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:	-4.84
MDCK Permeability:	2.2382413590094075e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.572
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.462
Plasma Protein Binding (PPB):	95.09710693359375%
Volume Distribution (VD):	1.491
Pgp-substrate:	4.559427261352539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.553
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.385
CYP2C9-substrate:	0.836
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.465
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.429

ADMET: Excretion

Clearance (CL):	13.56
Half-life (T1/2):	0.606

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.235
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.752
Maximum Recommended Daily Dose:	0.223
Skin Sensitization:	0.566
Carcinogencity:	0.596
Eye Corrosion:	0.039
Eye Irritation:	0.066
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC15975

Natural Product ID:	NPC15975
*Common Name:**	Desacetoxymatricarin
IUPAC Name:	(3S,3aS,9aS,9bS)-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
Synonyms:	Desacetoxymatricarin; Leucomisine
Standard InCHIKey:	BJPSSVHNEGMBDQ-NUZBWSBOSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,9-10,13-14H,4-5H2,1-3H3/t9-,10-,13-,14-/m0/s1
SMILES:	C[C@@H]1C(=O)O[C@H]2[C@H]1CCC(=C1[C@@H]2C(=CC1=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517040
PubChem CID:	167683
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
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/S0031-9422(99)00103-X]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19969457]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21314138]
NPO13745	Gynoxys verrucosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27057812]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31478	Artemisia sp	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1070	Matricaria suffruticosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19225	Artemisia sp.	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1070	Matricaria suffruticosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17892	Grosvenoria coelocaulis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1070	Matricaria suffruticosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13745	Gynoxys verrucosa	Species	Asteraceae	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
IC50	5
LD50	8
Others	6
Potency	10

Activity Type	# Activity
Cell Line	13
CELL-LINE	1
Individual Protein	11
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	Potency	=	4466.8	nM	PMID[570914]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[570915]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[570915]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[570915]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-3.63	%	PMID[570916]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	1122018.5	nM	PMID[570915]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.4	ug.mL-1	PMID[570919]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	0.4	ug.mL-1	PMID[570919]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	0.4	ug.mL-1	PMID[570919]
NPT574	Cell Line	XF498	Homo sapiens	IC50	=	0.4	ug.mL-1	PMID[570919]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	0.4	ug.mL-1	PMID[570919]
NPT466	Cell Line	U-937	Homo sapiens	LD50	>	20.0	uM	PMID[570920]
NPT1999	Cell Line	TUR	Homo sapiens	LD50	>	20.0	uM	PMID[570920]
NPT1970	Cell Line	THP-1	Homo sapiens	LD50	>	20.0	uM	PMID[570920]
NPT1649	Cell Line	MV4-11	Homo sapiens	LD50	>	20.0	uM	PMID[570920]
NPT6530	Cell Line	MOLM-13	Homo sapiens	LD50	>	20.0	uM	PMID[570920]
NPT2100	Cell Line	KG-1		LD50	>	20.0	uM	PMID[570920]
NPT2085	Cell Line	Kasumi 1		LD50	>	20.0	uM	PMID[570920]
NPT116	Cell Line	HL-60	Homo sapiens	LD50	>	20.0	uM	PMID[570920]
NPT2	Others	Unspecified		Potency	=	5.2	nM	PMID[570914]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	10417.9	nM	PMID[570914]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[570915]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[570914]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	0.28	%	PMID[570916]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	128.97	%	PMID[570917]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	118.49	%	PMID[570917]
NPT22036	CELL-LINE	HL	Homo sapiens	Activity	=	93.9	%	PMID[570918]
NPT5310	Organism	Chlamydophila pneumoniae	Chlamydophila pneumoniae	Inhibition	=	30.1	%	PMID[570918]

☑ 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 NPC15975 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	189
0.1-0.2	1312
0.2-0.3	6992
0.3-0.4	16144
0.4-0.5	8695
0.5-0.6	6186
0.6-0.7	2707
0.7-0.8	401
0.8-0.85	31
0.85-0.9	29
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC195785
0.9467	High Similarity	NPC255580
0.9467	High Similarity	NPC39411
0.9333	High Similarity	NPC302426
0.9306	High Similarity	NPC469641
0.9306	High Similarity	NPC469643
0.9103	High Similarity	NPC165287
0.9079	High Similarity	NPC69271
0.9079	High Similarity	NPC74673
0.9014	High Similarity	NPC296522
0.9014	High Similarity	NPC144511
0.8987	High Similarity	NPC78089
0.8961	High Similarity	NPC10276
0.8961	High Similarity	NPC35089
0.8947	High Similarity	NPC182550
0.8904	High Similarity	NPC472956
0.8889	High Similarity	NPC472955
0.8875	High Similarity	NPC107787
0.8861	High Similarity	NPC115786
0.8831	High Similarity	NPC276356
0.8816	High Similarity	NPC299235
0.88	High Similarity	NPC266159
0.88	High Similarity	NPC472967
0.8765	High Similarity	NPC237540
0.8734	High Similarity	NPC39588
0.8684	High Similarity	NPC65603
0.8667	High Similarity	NPC226669
0.8667	High Similarity	NPC138408
0.8667	High Similarity	NPC193351
0.8553	High Similarity	NPC472959
0.8533	High Similarity	NPC472966
0.8519	High Similarity	NPC33570
0.8519	High Similarity	NPC21471
0.8519	High Similarity	NPC161957
0.85	High Similarity	NPC215294
0.8493	Intermediate Similarity	NPC5714
0.8462	Intermediate Similarity	NPC264227
0.8462	Intermediate Similarity	NPC472965
0.8462	Intermediate Similarity	NPC63649
0.8442	Intermediate Similarity	NPC476794
0.8442	Intermediate Similarity	NPC470240
0.8434	Intermediate Similarity	NPC190718
0.8333	Intermediate Similarity	NPC268298
0.825	Intermediate Similarity	NPC301477
0.825	Intermediate Similarity	NPC281949
0.825	Intermediate Similarity	NPC25684
0.8243	Intermediate Similarity	NPC199557
0.8235	Intermediate Similarity	NPC129419
0.8228	Intermediate Similarity	NPC470239
0.8228	Intermediate Similarity	NPC470244
0.8182	Intermediate Similarity	NPC155587
0.8171	Intermediate Similarity	NPC156485
0.8125	Intermediate Similarity	NPC223904
0.8101	Intermediate Similarity	NPC472960
0.8077	Intermediate Similarity	NPC235906
0.8072	Intermediate Similarity	NPC235792
0.8052	Intermediate Similarity	NPC143979
0.8052	Intermediate Similarity	NPC320537
0.8025	Intermediate Similarity	NPC470241
0.8025	Intermediate Similarity	NPC475665
0.8	Intermediate Similarity	NPC91248
0.7976	Intermediate Similarity	NPC70422
0.7976	Intermediate Similarity	NPC104961
0.7976	Intermediate Similarity	NPC67493
0.7976	Intermediate Similarity	NPC70555
0.7975	Intermediate Similarity	NPC103987
0.7975	Intermediate Similarity	NPC41780
0.7975	Intermediate Similarity	NPC208223
0.7975	Intermediate Similarity	NPC187568
0.7975	Intermediate Similarity	NPC53581
0.7949	Intermediate Similarity	NPC469669
0.7949	Intermediate Similarity	NPC475771
0.7949	Intermediate Similarity	NPC324762
0.7949	Intermediate Similarity	NPC469678
0.7931	Intermediate Similarity	NPC74103
0.7931	Intermediate Similarity	NPC150978
0.7931	Intermediate Similarity	NPC70595
0.7931	Intermediate Similarity	NPC123177
0.7927	Intermediate Similarity	NPC173609
0.7927	Intermediate Similarity	NPC89555
0.7907	Intermediate Similarity	NPC4986
0.7901	Intermediate Similarity	NPC290508
0.7901	Intermediate Similarity	NPC6823
0.7901	Intermediate Similarity	NPC73052
0.7901	Intermediate Similarity	NPC293418
0.7875	Intermediate Similarity	NPC35574
0.7875	Intermediate Similarity	NPC128276
0.7857	Intermediate Similarity	NPC165162
0.7848	Intermediate Similarity	NPC123360
0.7841	Intermediate Similarity	NPC135776
0.7831	Intermediate Similarity	NPC318468
0.7831	Intermediate Similarity	NPC108045
0.7831	Intermediate Similarity	NPC475622
0.7821	Intermediate Similarity	NPC167049
0.7821	Intermediate Similarity	NPC469691
0.7821	Intermediate Similarity	NPC476355
0.7816	Intermediate Similarity	NPC253144
0.7816	Intermediate Similarity	NPC301969
0.7816	Intermediate Similarity	NPC37607
0.7805	Intermediate Similarity	NPC471325
0.7792	Intermediate Similarity	NPC163003
0.7792	Intermediate Similarity	NPC129665
0.7791	Intermediate Similarity	NPC224652
0.7778	Intermediate Similarity	NPC178277
0.7778	Intermediate Similarity	NPC617
0.7778	Intermediate Similarity	NPC469690
0.7765	Intermediate Similarity	NPC64153
0.7753	Intermediate Similarity	NPC167219
0.7753	Intermediate Similarity	NPC477131
0.775	Intermediate Similarity	NPC472014
0.775	Intermediate Similarity	NPC57744
0.775	Intermediate Similarity	NPC122264
0.7738	Intermediate Similarity	NPC472958
0.7738	Intermediate Similarity	NPC472957
0.7733	Intermediate Similarity	NPC476626
0.7727	Intermediate Similarity	NPC261607
0.7727	Intermediate Similarity	NPC284185
0.7727	Intermediate Similarity	NPC300312
0.7727	Intermediate Similarity	NPC133698
0.7727	Intermediate Similarity	NPC111114
0.7727	Intermediate Similarity	NPC131209
0.7701	Intermediate Similarity	NPC32922
0.7701	Intermediate Similarity	NPC52198
0.7701	Intermediate Similarity	NPC117405
0.7692	Intermediate Similarity	NPC58956
0.7692	Intermediate Similarity	NPC269206
0.7692	Intermediate Similarity	NPC295633
0.7683	Intermediate Similarity	NPC51507
0.7683	Intermediate Similarity	NPC304795
0.7667	Intermediate Similarity	NPC275960
0.7667	Intermediate Similarity	NPC48803
0.7667	Intermediate Similarity	NPC193645
0.7667	Intermediate Similarity	NPC90121
0.7647	Intermediate Similarity	NPC125290
0.7625	Intermediate Similarity	NPC474527
0.7625	Intermediate Similarity	NPC471726
0.7619	Intermediate Similarity	NPC193198
0.7619	Intermediate Similarity	NPC54468
0.7614	Intermediate Similarity	NPC62815
0.7595	Intermediate Similarity	NPC140287
0.759	Intermediate Similarity	NPC42470
0.759	Intermediate Similarity	NPC141810
0.7586	Intermediate Similarity	NPC215831
0.7564	Intermediate Similarity	NPC29328
0.7561	Intermediate Similarity	NPC89128
0.7561	Intermediate Similarity	NPC270126
0.7561	Intermediate Similarity	NPC469620
0.7558	Intermediate Similarity	NPC284902
0.7556	Intermediate Similarity	NPC323008
0.7556	Intermediate Similarity	NPC470013
0.7556	Intermediate Similarity	NPC470010
0.7556	Intermediate Similarity	NPC262133
0.7556	Intermediate Similarity	NPC198853
0.7532	Intermediate Similarity	NPC477449
0.7532	Intermediate Similarity	NPC477448
0.7529	Intermediate Similarity	NPC475100
0.7529	Intermediate Similarity	NPC100391
0.75	Intermediate Similarity	NPC73995
0.75	Intermediate Similarity	NPC35556
0.75	Intermediate Similarity	NPC244166
0.75	Intermediate Similarity	NPC475861
0.75	Intermediate Similarity	NPC246076
0.75	Intermediate Similarity	NPC169205
0.75	Intermediate Similarity	NPC178676
0.7473	Intermediate Similarity	NPC52044
0.7473	Intermediate Similarity	NPC67584
0.7473	Intermediate Similarity	NPC304886
0.7471	Intermediate Similarity	NPC475703
0.747	Intermediate Similarity	NPC258965
0.747	Intermediate Similarity	NPC156658
0.7468	Intermediate Similarity	NPC107783
0.7468	Intermediate Similarity	NPC92909
0.7468	Intermediate Similarity	NPC470237
0.7467	Intermediate Similarity	NPC474329
0.7467	Intermediate Similarity	NPC474304
0.7444	Intermediate Similarity	NPC477615
0.7442	Intermediate Similarity	NPC323765
0.7442	Intermediate Similarity	NPC470223
0.7442	Intermediate Similarity	NPC177932
0.7442	Intermediate Similarity	NPC215364
0.7442	Intermediate Similarity	NPC110405
0.7439	Intermediate Similarity	NPC108816
0.7439	Intermediate Similarity	NPC93763
0.7436	Intermediate Similarity	NPC475310
0.7419	Intermediate Similarity	NPC141191
0.7419	Intermediate Similarity	NPC54843
0.7416	Intermediate Similarity	NPC152467
0.7412	Intermediate Similarity	NPC470948
0.7412	Intermediate Similarity	NPC475947
0.7412	Intermediate Similarity	NPC245665
0.7412	Intermediate Similarity	NPC272814
0.7412	Intermediate Similarity	NPC22611
0.7412	Intermediate Similarity	NPC474703
0.7407	Intermediate Similarity	NPC226242
0.7407	Intermediate Similarity	NPC41017
0.7407	Intermediate Similarity	NPC473223
0.7403	Intermediate Similarity	NPC476614
0.7403	Intermediate Similarity	NPC470256
0.7391	Intermediate Similarity	NPC121036
0.7391	Intermediate Similarity	NPC213078

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 NPC15975 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1937
0.2-0.3	4191
0.3-0.4	1947
0.4-0.5	536
0.5-0.6	269
0.6-0.7	73
0.7-0.8	16
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
0.7907	Intermediate Similarity	NPD1695	Approved
0.7667	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1694	Approved
0.7386	Intermediate Similarity	NPD6903	Approved
0.7356	Intermediate Similarity	NPD7146	Approved
0.7356	Intermediate Similarity	NPD6684	Approved
0.7356	Intermediate Similarity	NPD6409	Approved
0.7356	Intermediate Similarity	NPD5330	Approved
0.7356	Intermediate Similarity	NPD7521	Approved
0.7356	Intermediate Similarity	NPD7334	Approved
0.7209	Intermediate Similarity	NPD5362	Discontinued
0.7191	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5369	Approved
0.7045	Intermediate Similarity	NPD5363	Approved
0.7045	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5207	Approved
0.7011	Intermediate Similarity	NPD7154	Phase 3
0.7	Intermediate Similarity	NPD5737	Approved
0.7	Intermediate Similarity	NPD6672	Approved
0.6989	Remote Similarity	NPD5282	Discontinued
0.6915	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4269	Approved
0.6897	Remote Similarity	NPD4270	Approved
0.6897	Remote Similarity	NPD6435	Approved
0.6897	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6399	Phase 3
0.6848	Remote Similarity	NPD5785	Approved
0.6809	Remote Similarity	NPD6001	Approved
0.68	Remote Similarity	NPD6008	Approved
0.6778	Remote Similarity	NPD5786	Approved
0.6705	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.6632	Remote Similarity	NPD7900	Approved
0.6632	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5208	Approved
0.6628	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3618	Phase 1
0.6582	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5695	Phase 3
0.6559	Remote Similarity	NPD6673	Approved
0.6559	Remote Similarity	NPD6904	Approved
0.6559	Remote Similarity	NPD6080	Approved
0.6556	Remote Similarity	NPD3666	Approved
0.6556	Remote Similarity	NPD3665	Phase 1
0.6556	Remote Similarity	NPD3133	Approved
0.6538	Remote Similarity	NPD6371	Approved
0.6531	Remote Similarity	NPD5696	Approved
0.6517	Remote Similarity	NPD3667	Approved
0.6489	Remote Similarity	NPD5692	Phase 3
0.6484	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7748	Approved
0.6444	Remote Similarity	NPD5331	Approved
0.6444	Remote Similarity	NPD5332	Approved
0.6429	Remote Similarity	NPD7902	Approved
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6084	Phase 2
0.6421	Remote Similarity	NPD5693	Phase 1
0.6421	Remote Similarity	NPD5694	Approved
0.6421	Remote Similarity	NPD6050	Approved
0.6413	Remote Similarity	NPD4249	Approved
0.6413	Remote Similarity	NPD6098	Approved
0.6413	Remote Similarity	NPD5279	Phase 3
0.6404	Remote Similarity	NPD4790	Discontinued
0.6383	Remote Similarity	NPD6101	Approved
0.6383	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4786	Approved
0.6374	Remote Similarity	NPD3668	Phase 3
0.6344	Remote Similarity	NPD3573	Approved
0.6344	Remote Similarity	NPD4250	Approved
0.6344	Remote Similarity	NPD4251	Approved
0.6316	Remote Similarity	NPD46	Approved
0.6316	Remote Similarity	NPD6698	Approved
0.6296	Remote Similarity	NPD7331	Phase 2
0.6292	Remote Similarity	NPD4819	Approved
0.6292	Remote Similarity	NPD4822	Approved
0.6292	Remote Similarity	NPD4821	Approved
0.6292	Remote Similarity	NPD4820	Approved
0.6279	Remote Similarity	NPD8039	Approved
0.6275	Remote Similarity	NPD6052	Approved
0.625	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD4271	Approved
0.625	Remote Similarity	NPD4268	Approved
0.625	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD5284	Approved
0.6211	Remote Similarity	NPD5328	Approved
0.62	Remote Similarity	NPD4225	Approved
0.619	Remote Similarity	NPD7320	Approved
0.6186	Remote Similarity	NPD5779	Approved
0.6186	Remote Similarity	NPD5778	Approved
0.6173	Remote Similarity	NPD7341	Phase 2
0.6162	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4223	Phase 3
0.6154	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD4221	Approved
0.6154	Remote Similarity	NPD7128	Approved
0.6154	Remote Similarity	NPD5739	Approved
0.6154	Remote Similarity	NPD6675	Approved
0.6132	Remote Similarity	NPD6372	Approved
0.6132	Remote Similarity	NPD6373	Approved
0.6111	Remote Similarity	NPD4695	Discontinued
0.6111	Remote Similarity	NPD6053	Discontinued
0.6098	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5697	Approved
0.6095	Remote Similarity	NPD5701	Approved
0.6082	Remote Similarity	NPD6079	Approved
0.6071	Remote Similarity	NPD4137	Phase 3
0.6064	Remote Similarity	NPD6422	Discontinued
0.6061	Remote Similarity	NPD5654	Approved
0.6044	Remote Similarity	NPD857	Phase 3
0.6042	Remote Similarity	NPD4753	Phase 2
0.604	Remote Similarity	NPD7638	Approved
0.6038	Remote Similarity	NPD6881	Approved
0.6038	Remote Similarity	NPD6011	Approved
0.6038	Remote Similarity	NPD6899	Approved
0.6022	Remote Similarity	NPD4197	Approved
0.602	Remote Similarity	NPD4202	Approved
0.6019	Remote Similarity	NPD6650	Approved
0.6019	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD4691	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD4747	Approved
0.5981	Remote Similarity	NPD6014	Approved
0.5981	Remote Similarity	NPD6012	Approved
0.5981	Remote Similarity	NPD6013	Approved
0.598	Remote Similarity	NPD7639	Approved
0.598	Remote Similarity	NPD7640	Approved
0.5957	Remote Similarity	NPD5329	Approved
0.5955	Remote Similarity	NPD4756	Discovery
0.5946	Remote Similarity	NPD28	Approved
0.5946	Remote Similarity	NPD29	Approved
0.5941	Remote Similarity	NPD5959	Approved
0.5938	Remote Similarity	NPD4518	Approved
0.593	Remote Similarity	NPD5276	Approved
0.5926	Remote Similarity	NPD7290	Approved
0.5926	Remote Similarity	NPD6883	Approved
0.5926	Remote Similarity	NPD7102	Approved
0.5918	Remote Similarity	NPD7983	Approved
0.5918	Remote Similarity	NPD8034	Phase 2
0.5918	Remote Similarity	NPD8035	Phase 2
0.59	Remote Similarity	NPD5210	Approved
0.59	Remote Similarity	NPD4629	Approved
0.5895	Remote Similarity	NPD5280	Approved
0.5895	Remote Similarity	NPD5690	Phase 2
0.5895	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4688	Approved
0.5895	Remote Similarity	NPD4623	Approved
0.5895	Remote Similarity	NPD4689	Approved
0.5895	Remote Similarity	NPD4519	Discontinued
0.5895	Remote Similarity	NPD5205	Approved
0.5895	Remote Similarity	NPD4138	Approved
0.5895	Remote Similarity	NPD4694	Approved
0.5895	Remote Similarity	NPD4693	Phase 3
0.5895	Remote Similarity	NPD4690	Approved
0.5893	Remote Similarity	NPD7115	Discovery
0.5889	Remote Similarity	NPD3617	Approved
0.5876	Remote Similarity	NPD5370	Suspended
0.5876	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD8130	Phase 1
0.5872	Remote Similarity	NPD6847	Approved
0.5872	Remote Similarity	NPD6869	Approved
0.5872	Remote Similarity	NPD6617	Approved
0.5859	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3197	Phase 1
0.5842	Remote Similarity	NPD5222	Approved
0.5842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5221	Approved
0.5826	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6882	Approved
0.5818	Remote Similarity	NPD8297	Approved
0.5816	Remote Similarity	NPD7838	Discovery
0.5806	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD4058	Approved
0.5795	Remote Similarity	NPD4687	Approved
0.5795	Remote Similarity	NPD5733	Approved
0.5794	Remote Similarity	NPD6412	Phase 2
0.5794	Remote Similarity	NPD6614	Approved
0.5789	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD3172	Approved
0.5784	Remote Similarity	NPD4755	Approved
0.5784	Remote Similarity	NPD5173	Approved
0.5783	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7094	Approved
0.5766	Remote Similarity	NPD6858	Approved
0.5765	Remote Similarity	NPD229	Approved
0.5758	Remote Similarity	NPD7637	Suspended
0.5758	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.575	Remote Similarity	NPD3198	Approved
0.5747	Remote Similarity	NPD5777	Approved
0.5741	Remote Similarity	NPD6686	Approved
0.5732	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3196	Approved
0.5714	Remote Similarity	NPD6051	Approved
0.5714	Remote Similarity	NPD3195	Phase 2
0.5714	Remote Similarity	NPD3704	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