NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	230.13
Volume:	249.361
LogP:	3.199
LogD:	3.12
LogS:	-2.314
# Rotatable Bonds:	0
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.693
Synthetic Accessibility Score:	4.874
Fsp3:	0.467
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:	-4.697
MDCK Permeability:	2.8671907784882933e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.739
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	90.92269134521484%
Volume Distribution (VD):	1.716
Pgp-substrate:	10.674924850463867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.788
CYP1A2-substrate:	0.756
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.482
CYP2C9-inhibitor:	0.103
CYP2C9-substrate:	0.268
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.633
CYP3A4-substrate:	0.276

ADMET: Excretion

Clearance (CL):	11.131
Half-life (T1/2):	0.464

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.779
Drug-inuced Liver Injury (DILI):	0.099
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.893
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.86
Carcinogencity:	0.94
Eye Corrosion:	0.181
Eye Irritation:	0.168
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC54996

Natural Product ID:	NPC54996
*Common Name:**	Atractylenolide I
IUPAC Name:	(4aS,8aS)-3,8a-dimethyl-5-methylidene-4a,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-2-one
Synonyms:	Atractylenolide I
Standard InCHIKey:	ZTVSGQPHMUYCRS-SWLSCSKDSA-N
Standard InCHI:	InChI=1S/C15H18O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h8,12H,1,4-7H2,2-3H3/t12-,15+/m0/s1
SMILES:	C=C1CCC[C@]2(C)C=C3C(=C(C)C(=O)O3)C[C@@H]12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449520
PubChem CID:	5321018
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17432574]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18787781]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302967]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228227]
NPO26787	Chloranthus anhuiensis	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29775304]
NPO40789	Atractylodes rhizomes	Species	Asteraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[6418860]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544564]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30858	Atractylodes japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30858	Atractylodes japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26787	Chloranthus anhuiensis	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16087	Atractylodes lancea	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	8
Others	16

Activity Type	# Activity
Cell Line	9
Individual Protein	2
NON-MOLECULAR	6
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	68.0	%	PMID[475916]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	107.0	%	PMID[475916]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	>	200000.0	nM	PMID[475917]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	>	200000.0	nM	PMID[475917]
NPT111	Cell Line	K562	Homo sapiens	Activity	>	50.0	%	PMID[475919]
NPT466	Cell Line	U-937	Homo sapiens	FC	=	2.0	n.a.	PMID[475919]
NPT15	Cell Line	Jurkat	Homo sapiens	FC	=	2.0	n.a.	PMID[475919]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	13.4	%	PMID[475919]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	18.1	%	PMID[475919]
NPT466	Cell Line	U-937	Homo sapiens	Activity	=	50.0	%	PMID[475919]
NPT111	Cell Line	K562	Homo sapiens	FC	=	2.0	n.a.	PMID[475919]
NPT610	Others	Molecular identity unknown		Activity	=	7.5	%	PMID[475919]
NPT610	Others	Molecular identity unknown		Activity	=	20.3	%	PMID[475919]
NPT610	Others	Molecular identity unknown		Activity	=	32.3	%	PMID[475919]
NPT610	Others	Molecular identity unknown		Activity	>	50.0	%	PMID[475919]
NPT610	Others	Molecular identity unknown		Activity	=	53.3	%	PMID[475919]
NPT610	Others	Molecular identity unknown		Activity	=	84.3	%	PMID[475919]
NPT610	Others	Molecular identity unknown		Activity	=	25.6	%	PMID[475919]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.23	ug.mL-1	PMID[475919]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14.91	ug.mL-1	PMID[475919]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24.11	ug.mL-1	PMID[475919]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24.44	ug.mL-1	PMID[475919]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	37.63	ug.mL-1	PMID[475919]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	44.67	ug.mL-1	PMID[475919]

☑ 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 NPC54996 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	178
0.1-0.2	1151
0.2-0.3	4920
0.3-0.4	14828
0.4-0.5	12044
0.5-0.6	6946
0.6-0.7	2279
0.7-0.8	337
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8831	High Similarity	NPC268827
0.8659	High Similarity	NPC472302
0.8442	Intermediate Similarity	NPC473825
0.8442	Intermediate Similarity	NPC189206
0.8333	Intermediate Similarity	NPC184737
0.8267	Intermediate Similarity	NPC181587
0.8243	Intermediate Similarity	NPC232812
0.8214	Intermediate Similarity	NPC471956
0.8133	Intermediate Similarity	NPC37929
0.8133	Intermediate Similarity	NPC64234
0.8133	Intermediate Similarity	NPC316029
0.8125	Intermediate Similarity	NPC10636
0.8095	Intermediate Similarity	NPC125925
0.8072	Intermediate Similarity	NPC189311
0.8023	Intermediate Similarity	NPC280149
0.8023	Intermediate Similarity	NPC221111
0.7975	Intermediate Similarity	NPC316500
0.7931	Intermediate Similarity	NPC2882
0.7927	Intermediate Similarity	NPC200513
0.7927	Intermediate Similarity	NPC186276
0.7927	Intermediate Similarity	NPC471218
0.7875	Intermediate Similarity	NPC471220
0.7867	Intermediate Similarity	NPC313444
0.7865	Intermediate Similarity	NPC295347
0.7857	Intermediate Similarity	NPC472442
0.7848	Intermediate Similarity	NPC4509
0.7841	Intermediate Similarity	NPC472954
0.7838	Intermediate Similarity	NPC116013
0.7831	Intermediate Similarity	NPC472440
0.7831	Intermediate Similarity	NPC311070
0.7831	Intermediate Similarity	NPC12283
0.7831	Intermediate Similarity	NPC193198
0.7831	Intermediate Similarity	NPC477124
0.7831	Intermediate Similarity	NPC474193
0.7831	Intermediate Similarity	NPC22611
0.7816	Intermediate Similarity	NPC212679
0.7816	Intermediate Similarity	NPC220454
0.7816	Intermediate Similarity	NPC310479
0.7816	Intermediate Similarity	NPC182136
0.7816	Intermediate Similarity	NPC469595
0.7805	Intermediate Similarity	NPC282293
0.7791	Intermediate Similarity	NPC226863
0.7778	Intermediate Similarity	NPC260796
0.7778	Intermediate Similarity	NPC16967
0.7778	Intermediate Similarity	NPC150646
0.7765	Intermediate Similarity	NPC471219
0.7763	Intermediate Similarity	NPC265574
0.7753	Intermediate Similarity	NPC191521
0.7738	Intermediate Similarity	NPC30486
0.7738	Intermediate Similarity	NPC96055
0.7738	Intermediate Similarity	NPC318515
0.7711	Intermediate Similarity	NPC268122
0.7711	Intermediate Similarity	NPC16321
0.7701	Intermediate Similarity	NPC173042
0.7701	Intermediate Similarity	NPC5509
0.7701	Intermediate Similarity	NPC284561
0.7692	Intermediate Similarity	NPC208094
0.7683	Intermediate Similarity	NPC195424
0.7647	Intermediate Similarity	NPC473251
0.7647	Intermediate Similarity	NPC65661
0.7647	Intermediate Similarity	NPC86316
0.7647	Intermediate Similarity	NPC42586
0.7647	Intermediate Similarity	NPC106416
0.7647	Intermediate Similarity	NPC30984
0.7647	Intermediate Similarity	NPC474013
0.764	Intermediate Similarity	NPC205034
0.764	Intermediate Similarity	NPC162615
0.764	Intermediate Similarity	NPC1108
0.764	Intermediate Similarity	NPC152778
0.7619	Intermediate Similarity	NPC118423
0.7619	Intermediate Similarity	NPC472377
0.7619	Intermediate Similarity	NPC30502
0.7609	Intermediate Similarity	NPC181147
0.76	Intermediate Similarity	NPC191233
0.76	Intermediate Similarity	NPC315115
0.7564	Intermediate Similarity	NPC257618
0.7561	Intermediate Similarity	NPC242767
0.7558	Intermediate Similarity	NPC131813
0.7556	Intermediate Similarity	NPC477129
0.7556	Intermediate Similarity	NPC477130
0.7531	Intermediate Similarity	NPC316324
0.7531	Intermediate Similarity	NPC315394
0.7529	Intermediate Similarity	NPC474693
0.7529	Intermediate Similarity	NPC475100
0.7529	Intermediate Similarity	NPC149869
0.75	Intermediate Similarity	NPC472266
0.75	Intermediate Similarity	NPC177141
0.75	Intermediate Similarity	NPC470734
0.75	Intermediate Similarity	NPC178676
0.75	Intermediate Similarity	NPC94200
0.7473	Intermediate Similarity	NPC474909
0.7473	Intermediate Similarity	NPC209355
0.7471	Intermediate Similarity	NPC475678
0.7471	Intermediate Similarity	NPC473891
0.7471	Intermediate Similarity	NPC312561
0.7471	Intermediate Similarity	NPC477228
0.7471	Intermediate Similarity	NPC476600
0.747	Intermediate Similarity	NPC47747
0.7468	Intermediate Similarity	NPC222244
0.7468	Intermediate Similarity	NPC16349
0.7467	Intermediate Similarity	NPC220766
0.7444	Intermediate Similarity	NPC475657
0.7444	Intermediate Similarity	NPC115021
0.7442	Intermediate Similarity	NPC474694
0.7442	Intermediate Similarity	NPC473659
0.7442	Intermediate Similarity	NPC177932
0.7442	Intermediate Similarity	NPC471795
0.7442	Intermediate Similarity	NPC475860
0.7436	Intermediate Similarity	NPC315597
0.7436	Intermediate Similarity	NPC315285
0.7419	Intermediate Similarity	NPC278673
0.7416	Intermediate Similarity	NPC273199
0.7416	Intermediate Similarity	NPC51486
0.7416	Intermediate Similarity	NPC280592
0.7416	Intermediate Similarity	NPC469372
0.7416	Intermediate Similarity	NPC8062
0.7416	Intermediate Similarity	NPC213636
0.7416	Intermediate Similarity	NPC253177
0.7412	Intermediate Similarity	NPC288281
0.7407	Intermediate Similarity	NPC473223
0.7407	Intermediate Similarity	NPC40353
0.7407	Intermediate Similarity	NPC27205
0.7403	Intermediate Similarity	NPC476945
0.7391	Intermediate Similarity	NPC473153
0.7391	Intermediate Similarity	NPC112654
0.7386	Intermediate Similarity	NPC24816
0.7386	Intermediate Similarity	NPC215831
0.7386	Intermediate Similarity	NPC106332
0.7386	Intermediate Similarity	NPC472810
0.7386	Intermediate Similarity	NPC93411
0.7386	Intermediate Similarity	NPC472809
0.7381	Intermediate Similarity	NPC40228
0.7381	Intermediate Similarity	NPC475665
0.7368	Intermediate Similarity	NPC185587
0.7363	Intermediate Similarity	NPC120351
0.7363	Intermediate Similarity	NPC38830
0.7363	Intermediate Similarity	NPC470255
0.7363	Intermediate Similarity	NPC471994
0.7363	Intermediate Similarity	NPC166143
0.7356	Intermediate Similarity	NPC220478
0.7356	Intermediate Similarity	NPC168248
0.7342	Intermediate Similarity	NPC5734
0.734	Intermediate Similarity	NPC54705
0.7333	Intermediate Similarity	NPC471329
0.7333	Intermediate Similarity	NPC472814
0.7333	Intermediate Similarity	NPC177037
0.7333	Intermediate Similarity	NPC296114
0.7333	Intermediate Similarity	NPC289479
0.7326	Intermediate Similarity	NPC32223
0.7326	Intermediate Similarity	NPC71626
0.7317	Intermediate Similarity	NPC41780
0.7317	Intermediate Similarity	NPC97377
0.7317	Intermediate Similarity	NPC187568
0.7317	Intermediate Similarity	NPC472300
0.7308	Intermediate Similarity	NPC470693
0.7303	Intermediate Similarity	NPC174342
0.7303	Intermediate Similarity	NPC251528
0.7303	Intermediate Similarity	NPC73995
0.7303	Intermediate Similarity	NPC168131
0.7303	Intermediate Similarity	NPC50488
0.7303	Intermediate Similarity	NPC474396
0.7294	Intermediate Similarity	NPC256112
0.7284	Intermediate Similarity	NPC228978
0.7284	Intermediate Similarity	NPC65650
0.7283	Intermediate Similarity	NPC171395
0.7273	Intermediate Similarity	NPC181327
0.7273	Intermediate Similarity	NPC171722
0.7273	Intermediate Similarity	NPC75315
0.7273	Intermediate Similarity	NPC163016
0.7273	Intermediate Similarity	NPC471796
0.7263	Intermediate Similarity	NPC194028
0.7263	Intermediate Similarity	NPC168319
0.7262	Intermediate Similarity	NPC233332
0.7262	Intermediate Similarity	NPC469802
0.726	Intermediate Similarity	NPC133600
0.7253	Intermediate Similarity	NPC139692
0.7253	Intermediate Similarity	NPC472303
0.725	Intermediate Similarity	NPC476489
0.725	Intermediate Similarity	NPC476490
0.7241	Intermediate Similarity	NPC253604
0.7241	Intermediate Similarity	NPC110405
0.7241	Intermediate Similarity	NPC471185
0.7237	Intermediate Similarity	NPC182794
0.7234	Intermediate Similarity	NPC474440
0.7234	Intermediate Similarity	NPC92275
0.7229	Intermediate Similarity	NPC35574
0.7229	Intermediate Similarity	NPC474005
0.7229	Intermediate Similarity	NPC169095
0.7229	Intermediate Similarity	NPC4827
0.7222	Intermediate Similarity	NPC281942
0.7222	Intermediate Similarity	NPC78973
0.7222	Intermediate Similarity	NPC152467
0.7222	Intermediate Similarity	NPC232426
0.7222	Intermediate Similarity	NPC212369
0.7222	Intermediate Similarity	NPC477782
0.7216	Intermediate Similarity	NPC200861
0.7216	Intermediate Similarity	NPC472822
0.7215	Intermediate Similarity	NPC469660
0.7209	Intermediate Similarity	NPC321385
0.7209	Intermediate Similarity	NPC42476

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 NPC54996 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1278
0.2-0.3	3930
0.3-0.4	2588
0.4-0.5	845
0.5-0.6	277
0.6-0.7	62
0.7-0.8	2
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
0.7927	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1694	Approved
0.7284	Intermediate Similarity	NPD8039	Approved
0.7143	Intermediate Similarity	NPD5693	Phase 1
0.7105	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5207	Approved
0.7033	Intermediate Similarity	NPD5692	Phase 3
0.6966	Remote Similarity	NPD7146	Approved
0.6966	Remote Similarity	NPD7334	Approved
0.6966	Remote Similarity	NPD6684	Approved
0.6966	Remote Similarity	NPD5330	Approved
0.6966	Remote Similarity	NPD7521	Approved
0.6966	Remote Similarity	NPD6409	Approved
0.6957	Remote Similarity	NPD6050	Approved
0.6957	Remote Similarity	NPD5694	Approved
0.6923	Remote Similarity	NPD6051	Approved
0.6897	Remote Similarity	NPD5209	Approved
0.6842	Remote Similarity	NPD4191	Approved
0.6842	Remote Similarity	NPD4193	Approved
0.6842	Remote Similarity	NPD4194	Approved
0.6842	Remote Similarity	NPD4192	Approved
0.6813	Remote Similarity	NPD6903	Approved
0.6813	Remote Similarity	NPD5737	Approved
0.6813	Remote Similarity	NPD6672	Approved
0.6813	Remote Similarity	NPD5208	Approved
0.6813	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6673	Approved
0.6739	Remote Similarity	NPD6080	Approved
0.6739	Remote Similarity	NPD6904	Approved
0.6703	Remote Similarity	NPD3573	Approved
0.6701	Remote Similarity	NPD4225	Approved
0.6701	Remote Similarity	NPD7638	Approved
0.6633	Remote Similarity	NPD7640	Approved
0.6633	Remote Similarity	NPD7639	Approved
0.6596	Remote Similarity	NPD5281	Approved
0.6596	Remote Similarity	NPD5284	Approved
0.6593	Remote Similarity	NPD6098	Approved
0.6562	Remote Similarity	NPD5654	Approved
0.6559	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5276	Approved
0.6477	Remote Similarity	NPD4695	Discontinued
0.6458	Remote Similarity	NPD6001	Approved
0.6429	Remote Similarity	NPD5959	Approved
0.6421	Remote Similarity	NPD7637	Suspended
0.6413	Remote Similarity	NPD5280	Approved
0.6413	Remote Similarity	NPD5279	Phase 3
0.6413	Remote Similarity	NPD4519	Discontinued
0.6413	Remote Similarity	NPD4694	Approved
0.6413	Remote Similarity	NPD4623	Approved
0.6392	Remote Similarity	NPD5695	Phase 3
0.6392	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4195	Approved
0.6353	Remote Similarity	NPD5733	Approved
0.6353	Remote Similarity	NPD4687	Approved
0.6353	Remote Similarity	NPD4058	Approved
0.6346	Remote Similarity	NPD6686	Approved
0.6333	Remote Similarity	NPD4221	Approved
0.6333	Remote Similarity	NPD4223	Phase 3
0.63	Remote Similarity	NPD6404	Discontinued
0.6289	Remote Similarity	NPD7748	Approved
0.6289	Remote Similarity	NPD7900	Approved
0.6289	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4137	Phase 3
0.6263	Remote Similarity	NPD6083	Phase 2
0.6263	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD3617	Approved
0.6214	Remote Similarity	NPD5909	Discontinued
0.62	Remote Similarity	NPD5696	Approved
0.6196	Remote Similarity	NPD3666	Approved
0.6196	Remote Similarity	NPD4197	Approved
0.6196	Remote Similarity	NPD3665	Phase 1
0.6196	Remote Similarity	NPD3133	Approved
0.619	Remote Similarity	NPD4747	Approved
0.619	Remote Similarity	NPD4691	Approved
0.6186	Remote Similarity	NPD5779	Approved
0.6186	Remote Similarity	NPD5778	Approved
0.6186	Remote Similarity	NPD6399	Phase 3
0.6163	Remote Similarity	NPD6926	Approved
0.6163	Remote Similarity	NPD6924	Approved
0.6146	Remote Similarity	NPD7838	Discovery
0.6146	Remote Similarity	NPD4096	Approved
0.6139	Remote Similarity	NPD6648	Approved
0.6136	Remote Similarity	NPD4756	Discovery
0.6129	Remote Similarity	NPD5329	Approved
0.6106	Remote Similarity	NPD7503	Approved
0.6105	Remote Similarity	NPD4518	Approved
0.61	Remote Similarity	NPD7902	Approved
0.6095	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6695	Phase 3
0.6082	Remote Similarity	NPD7515	Phase 2
0.6064	Remote Similarity	NPD5690	Phase 2
0.6064	Remote Similarity	NPD4689	Approved
0.6064	Remote Similarity	NPD4690	Approved
0.6064	Remote Similarity	NPD5205	Approved
0.6064	Remote Similarity	NPD4138	Approved
0.6064	Remote Similarity	NPD4688	Approved
0.6064	Remote Similarity	NPD3618	Phase 1
0.6064	Remote Similarity	NPD4693	Phase 3
0.6061	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6101	Approved
0.6023	Remote Similarity	NPD6933	Approved
0.6022	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD6929	Approved
0.5981	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5785	Approved
0.5978	Remote Similarity	NPD3667	Approved
0.5963	Remote Similarity	NPD6053	Discontinued
0.5962	Remote Similarity	NPD6052	Approved
0.596	Remote Similarity	NPD5707	Approved
0.5957	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD1696	Phase 3
0.5934	Remote Similarity	NPD6931	Approved
0.5934	Remote Similarity	NPD6930	Phase 2
0.593	Remote Similarity	NPD4243	Approved
0.5926	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7154	Phase 3
0.5909	Remote Similarity	NPD8264	Approved
0.5895	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7115	Discovery
0.5889	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6923	Approved
0.5882	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6922	Approved
0.5876	Remote Similarity	NPD5328	Approved
0.5876	Remote Similarity	NPD1695	Approved
0.5876	Remote Similarity	NPD4753	Phase 2
0.5859	Remote Similarity	NPD5133	Approved
0.5851	Remote Similarity	NPD4786	Approved
0.5851	Remote Similarity	NPD3668	Phase 3
0.5849	Remote Similarity	NPD6675	Approved
0.5849	Remote Similarity	NPD6402	Approved
0.5849	Remote Similarity	NPD6008	Approved
0.5849	Remote Similarity	NPD7128	Approved
0.5849	Remote Similarity	NPD5739	Approved
0.5843	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7732	Phase 3
0.5833	Remote Similarity	NPD7750	Discontinued
0.5833	Remote Similarity	NPD7524	Approved
0.5823	Remote Similarity	NPD287	Approved
0.5816	Remote Similarity	NPD6698	Approved
0.5816	Remote Similarity	NPD46	Approved
0.5814	Remote Similarity	NPD7143	Approved
0.5814	Remote Similarity	NPD7144	Approved
0.5795	Remote Similarity	NPD4785	Approved
0.5795	Remote Similarity	NPD4784	Approved
0.5794	Remote Similarity	NPD5701	Approved
0.5794	Remote Similarity	NPD5697	Approved
0.5794	Remote Similarity	NPD6614	Approved
0.5789	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.578	Remote Similarity	NPD2067	Discontinued
0.5778	Remote Similarity	NPD5776	Phase 2
0.5778	Remote Similarity	NPD6925	Approved
0.5776	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5344	Discontinued
0.5766	Remote Similarity	NPD6858	Approved
0.5766	Remote Similarity	NPD7094	Approved
0.5765	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD7509	Discontinued
0.5761	Remote Similarity	NPD7514	Phase 3
0.5761	Remote Similarity	NPD7332	Phase 2
0.5758	Remote Similarity	NPD6079	Approved
0.5747	Remote Similarity	NPD7150	Approved
0.5747	Remote Similarity	NPD7151	Approved
0.5747	Remote Similarity	NPD7152	Approved
0.5745	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6011	Approved
0.5741	Remote Similarity	NPD6899	Approved
0.5741	Remote Similarity	NPD7320	Approved
0.5741	Remote Similarity	NPD6881	Approved
0.573	Remote Similarity	NPD4190	Phase 3
0.573	Remote Similarity	NPD5275	Approved
0.573	Remote Similarity	NPD7339	Approved
0.573	Remote Similarity	NPD6942	Approved
0.5728	Remote Similarity	NPD5926	Approved
0.5714	Remote Similarity	NPD7331	Phase 2
0.5714	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7145	Approved
0.5702	Remote Similarity	NPD7328	Approved
0.5702	Remote Similarity	NPD7327	Approved
0.57	Remote Similarity	NPD4202	Approved
0.5699	Remote Similarity	NPD6902	Approved
0.5688	Remote Similarity	NPD6014	Approved
0.5688	Remote Similarity	NPD6373	Approved
0.5688	Remote Similarity	NPD6372	Approved
0.5688	Remote Similarity	NPD6012	Approved
0.5688	Remote Similarity	NPD6013	Approved
0.5686	Remote Similarity	NPD7614	Phase 1
0.567	Remote Similarity	NPD1282	Approved
0.5652	Remote Similarity	NPD7516	Approved
0.5652	Remote Similarity	NPD7645	Phase 2
0.5644	Remote Similarity	NPD5282	Discontinued
0.5644	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD7102	Approved
0.5636	Remote Similarity	NPD6883	Approved
0.5636	Remote Similarity	NPD7290	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