NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	258.152
LogP:	1.759
LogD:	1.257
LogS:	-1.828
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	4.746
Fsp3:	0.6
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:	-4.818
MDCK Permeability:	4.229438127367757e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.75
Plasma Protein Binding (PPB):	60.373695373535156%
Volume Distribution (VD):	0.972
Pgp-substrate:	58.15412902832031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.199
CYP1A2-substrate:	0.483
CYP2C19-inhibitor:	0.184
CYP2C19-substrate:	0.706
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.705
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	11.728
Half-life (T1/2):	0.436

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.166
Drug-inuced Liver Injury (DILI):	0.488
AMES Toxicity:	0.452
Rat Oral Acute Toxicity:	0.807
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.557
Carcinogencity:	0.837
Eye Corrosion:	0.196
Eye Irritation:	0.055
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC110405

Natural Product ID:	NPC110405
*Common Name:**	2-Oxoalantolactone
IUPAC Name:	(3aR,5S,8aS,9aR)-5,8a-dimethyl-3-methylidene-3a,5,6,8,9,9a-hexahydrobenzo[f][1]benzofuran-2,7-dione
Synonyms:
Standard InCHIKey:	DSTJGYCTYZXZNH-DGFVYPATSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-8-4-10(16)6-15(3)7-13-11(5-12(8)15)9(2)14(17)18-13/h5,8,11,13H,2,4,6-7H2,1,3H3/t8-,11+,13+,15+/m0/s1
SMILES:	O=C1C[C@H](C)C2=C[C@H]3[C@@H](C[C@]2(C1)C)OC(=O)C3=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2380793
PubChem CID:	73356469
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[10364842]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[12392098]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24996657]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[25767328]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17755	Inula helenium	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	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	50003.45	nM	PMID[455772]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[455772]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	>	30000.0	nM	PMID[455772]

☑ 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 NPC110405 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	168
0.1-0.2	1144
0.2-0.3	5112
0.3-0.4	12200
0.4-0.5	10878
0.5-0.6	6824
0.6-0.7	5060
0.7-0.8	1235
0.8-0.85	59
0.85-0.9	12
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.962	High Similarity	NPC178676
0.9405	High Similarity	NPC152467
0.9059	High Similarity	NPC73995
0.8941	High Similarity	NPC215831
0.8875	High Similarity	NPC35574
0.8795	High Similarity	NPC22611
0.8736	High Similarity	NPC158488
0.8659	High Similarity	NPC195424
0.8636	High Similarity	NPC233345
0.8636	High Similarity	NPC186363
0.8571	High Similarity	NPC474343
0.8554	High Similarity	NPC475665
0.8519	High Similarity	NPC41780
0.8519	High Similarity	NPC187568
0.8506	High Similarity	NPC226863
0.8506	High Similarity	NPC277771
0.8488	Intermediate Similarity	NPC220478
0.8471	Intermediate Similarity	NPC30486
0.8452	Intermediate Similarity	NPC186276
0.8452	Intermediate Similarity	NPC226988
0.8444	Intermediate Similarity	NPC250075
0.8372	Intermediate Similarity	NPC189311
0.8372	Intermediate Similarity	NPC177932
0.8372	Intermediate Similarity	NPC161957
0.8353	Intermediate Similarity	NPC193198
0.8353	Intermediate Similarity	NPC194637
0.8353	Intermediate Similarity	NPC470948
0.8352	Intermediate Similarity	NPC183012
0.8333	Intermediate Similarity	NPC38642
0.8333	Intermediate Similarity	NPC475657
0.8315	Intermediate Similarity	NPC220454
0.8315	Intermediate Similarity	NPC469595
0.8315	Intermediate Similarity	NPC212679
0.8295	Intermediate Similarity	NPC477128
0.8293	Intermediate Similarity	NPC65603
0.828	Intermediate Similarity	NPC23364
0.8272	Intermediate Similarity	NPC155587
0.8272	Intermediate Similarity	NPC226669
0.8272	Intermediate Similarity	NPC138408
0.8272	Intermediate Similarity	NPC193351
0.8256	Intermediate Similarity	NPC219011
0.8242	Intermediate Similarity	NPC470697
0.8242	Intermediate Similarity	NPC477129
0.8242	Intermediate Similarity	NPC477130
0.8222	Intermediate Similarity	NPC49420
0.8202	Intermediate Similarity	NPC168131
0.8193	Intermediate Similarity	NPC471220
0.8172	Intermediate Similarity	NPC38530
0.8172	Intermediate Similarity	NPC84335
0.8171	Intermediate Similarity	NPC41017
0.8171	Intermediate Similarity	NPC235906
0.814	Intermediate Similarity	NPC39588
0.814	Intermediate Similarity	NPC215294
0.8125	Intermediate Similarity	NPC254202
0.8118	Intermediate Similarity	NPC10276
0.8118	Intermediate Similarity	NPC35089
0.8095	Intermediate Similarity	NPC150646
0.8085	Intermediate Similarity	NPC252295
0.8085	Intermediate Similarity	NPC216478
0.8085	Intermediate Similarity	NPC176845
0.8072	Intermediate Similarity	NPC470240
0.8072	Intermediate Similarity	NPC476794
0.8068	Intermediate Similarity	NPC6979
0.8065	Intermediate Similarity	NPC307164
0.8046	Intermediate Similarity	NPC159635
0.8046	Intermediate Similarity	NPC470011
0.8046	Intermediate Similarity	NPC139566
0.8046	Intermediate Similarity	NPC149869
0.8043	Intermediate Similarity	NPC476596
0.8041	Intermediate Similarity	NPC189616
0.8023	Intermediate Similarity	NPC200513
0.8022	Intermediate Similarity	NPC65513
0.8	Intermediate Similarity	NPC288699
0.8	Intermediate Similarity	NPC284561
0.8	Intermediate Similarity	NPC474396
0.8	Intermediate Similarity	NPC50488
0.8	Intermediate Similarity	NPC223904
0.8	Intermediate Similarity	NPC472644
0.8	Intermediate Similarity	NPC302426
0.8	Intermediate Similarity	NPC73052
0.8	Intermediate Similarity	NPC293418
0.8	Intermediate Similarity	NPC5509
0.8	Intermediate Similarity	NPC290508
0.7979	Intermediate Similarity	NPC226986
0.7979	Intermediate Similarity	NPC292133
0.7978	Intermediate Similarity	NPC175293
0.7978	Intermediate Similarity	NPC181103
0.7978	Intermediate Similarity	NPC305029
0.7976	Intermediate Similarity	NPC472960
0.7957	Intermediate Similarity	NPC316215
0.7957	Intermediate Similarity	NPC473369
0.7955	Intermediate Similarity	NPC21471
0.7955	Intermediate Similarity	NPC476678
0.7955	Intermediate Similarity	NPC33570
0.7955	Intermediate Similarity	NPC52628
0.7952	Intermediate Similarity	NPC40353
0.7938	Intermediate Similarity	NPC132395
0.7938	Intermediate Similarity	NPC471365
0.7938	Intermediate Similarity	NPC471364
0.7935	Intermediate Similarity	NPC166346
0.7935	Intermediate Similarity	NPC476598
0.7935	Intermediate Similarity	NPC79117
0.7935	Intermediate Similarity	NPC471571
0.7935	Intermediate Similarity	NPC476597
0.7931	Intermediate Similarity	NPC272814
0.7931	Intermediate Similarity	NPC222358
0.7917	Intermediate Similarity	NPC310981
0.7917	Intermediate Similarity	NPC81530
0.7917	Intermediate Similarity	NPC472643
0.7912	Intermediate Similarity	NPC469372
0.7912	Intermediate Similarity	NPC471818
0.7907	Intermediate Similarity	NPC282293
0.7907	Intermediate Similarity	NPC281949
0.7907	Intermediate Similarity	NPC301477
0.7907	Intermediate Similarity	NPC25684
0.7901	Intermediate Similarity	NPC163003
0.7895	Intermediate Similarity	NPC222011
0.7882	Intermediate Similarity	NPC472965
0.7882	Intermediate Similarity	NPC264227
0.7882	Intermediate Similarity	NPC470239
0.7882	Intermediate Similarity	NPC63649
0.7882	Intermediate Similarity	NPC617
0.7882	Intermediate Similarity	NPC470244
0.7882	Intermediate Similarity	NPC469690
0.7882	Intermediate Similarity	NPC182550
0.7879	Intermediate Similarity	NPC133422
0.7879	Intermediate Similarity	NPC110496
0.7872	Intermediate Similarity	NPC112654
0.7865	Intermediate Similarity	NPC9231
0.7865	Intermediate Similarity	NPC477920
0.7865	Intermediate Similarity	NPC85698
0.7865	Intermediate Similarity	NPC250981
0.7865	Intermediate Similarity	NPC329692
0.7857	Intermediate Similarity	NPC316500
0.7857	Intermediate Similarity	NPC122264
0.7857	Intermediate Similarity	NPC118911
0.7849	Intermediate Similarity	NPC476415
0.7849	Intermediate Similarity	NPC473434
0.7849	Intermediate Similarity	NPC38830
0.7849	Intermediate Similarity	NPC148463
0.7849	Intermediate Similarity	NPC471446
0.7849	Intermediate Similarity	NPC474841
0.7841	Intermediate Similarity	NPC475100
0.7841	Intermediate Similarity	NPC100391
0.7835	Intermediate Similarity	NPC136289
0.7826	Intermediate Similarity	NPC473944
0.7826	Intermediate Similarity	NPC72845
0.7826	Intermediate Similarity	NPC70595
0.7826	Intermediate Similarity	NPC218301
0.7826	Intermediate Similarity	NPC74103
0.7826	Intermediate Similarity	NPC150978
0.7826	Intermediate Similarity	NPC123177
0.7822	Intermediate Similarity	NPC253906
0.7816	Intermediate Similarity	NPC173609
0.7812	Intermediate Similarity	NPC473219
0.7812	Intermediate Similarity	NPC476933
0.7812	Intermediate Similarity	NPC470906
0.7812	Intermediate Similarity	NPC476303
0.7812	Intermediate Similarity	NPC476274
0.7812	Intermediate Similarity	NPC470761
0.7805	Intermediate Similarity	NPC58956
0.7805	Intermediate Similarity	NPC269206
0.7805	Intermediate Similarity	NPC295633
0.7802	Intermediate Similarity	NPC174765
0.7802	Intermediate Similarity	NPC116620
0.78	Intermediate Similarity	NPC275539
0.78	Intermediate Similarity	NPC189075
0.7791	Intermediate Similarity	NPC69271
0.7791	Intermediate Similarity	NPC276356
0.7791	Intermediate Similarity	NPC74673
0.7789	Intermediate Similarity	NPC69385
0.7789	Intermediate Similarity	NPC285513
0.7789	Intermediate Similarity	NPC254496
0.7778	Intermediate Similarity	NPC312561
0.7778	Intermediate Similarity	NPC469607
0.7778	Intermediate Similarity	NPC470012
0.7766	Intermediate Similarity	NPC274417
0.7766	Intermediate Similarity	NPC470978
0.7766	Intermediate Similarity	NPC90014
0.7766	Intermediate Similarity	NPC56369
0.7766	Intermediate Similarity	NPC470974
0.7753	Intermediate Similarity	NPC470223
0.7753	Intermediate Similarity	NPC65661
0.7753	Intermediate Similarity	NPC86316
0.7753	Intermediate Similarity	NPC106416
0.7753	Intermediate Similarity	NPC323765
0.7742	Intermediate Similarity	NPC229976
0.7742	Intermediate Similarity	NPC139692
0.7742	Intermediate Similarity	NPC115021
0.7738	Intermediate Similarity	NPC27205
0.7738	Intermediate Similarity	NPC473223
0.7738	Intermediate Similarity	NPC92489
0.7732	Intermediate Similarity	NPC473384
0.7732	Intermediate Similarity	NPC224720
0.7732	Intermediate Similarity	NPC476223
0.7732	Intermediate Similarity	NPC476240
0.7727	Intermediate Similarity	NPC54468
0.7727	Intermediate Similarity	NPC118423
0.7723	Intermediate Similarity	NPC112457
0.7717	Intermediate Similarity	NPC8062

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 NPC110405 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1391
0.2-0.3	4003
0.3-0.4	2416
0.4-0.5	713
0.5-0.6	264
0.6-0.7	183
0.7-0.8	23
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8372	Intermediate Similarity	NPD1694	Approved
0.8023	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6409	Approved
0.7667	Intermediate Similarity	NPD6684	Approved
0.7667	Intermediate Similarity	NPD7146	Approved
0.7667	Intermediate Similarity	NPD7334	Approved
0.7667	Intermediate Similarity	NPD5330	Approved
0.7667	Intermediate Similarity	NPD7521	Approved
0.7582	Intermediate Similarity	NPD3573	Approved
0.7579	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6903	Approved
0.7426	Intermediate Similarity	NPD6008	Approved
0.7347	Intermediate Similarity	NPD4225	Approved
0.7312	Intermediate Similarity	NPD6672	Approved
0.7312	Intermediate Similarity	NPD5737	Approved
0.7292	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7900	Approved
0.7263	Intermediate Similarity	NPD5693	Phase 1
0.7222	Intermediate Similarity	NPD3667	Approved
0.7209	Intermediate Similarity	NPD8039	Approved
0.7158	Intermediate Similarity	NPD5207	Approved
0.7113	Intermediate Similarity	NPD7748	Approved
0.7097	Intermediate Similarity	NPD3618	Phase 1
0.7083	Intermediate Similarity	NPD6079	Approved
0.7071	Intermediate Similarity	NPD7902	Approved
0.7065	Intermediate Similarity	NPD4786	Approved
0.7065	Intermediate Similarity	NPD3668	Phase 3
0.7053	Intermediate Similarity	NPD1695	Approved
0.7053	Intermediate Similarity	NPD5328	Approved
0.7041	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5697	Approved
0.6952	Remote Similarity	NPD6881	Approved
0.6952	Remote Similarity	NPD6899	Approved
0.6952	Remote Similarity	NPD6011	Approved
0.6947	Remote Similarity	NPD5208	Approved
0.6939	Remote Similarity	NPD6001	Approved
0.6923	Remote Similarity	NPD6402	Approved
0.6923	Remote Similarity	NPD7128	Approved
0.6923	Remote Similarity	NPD5739	Approved
0.6923	Remote Similarity	NPD6675	Approved
0.6916	Remote Similarity	NPD6649	Approved
0.6916	Remote Similarity	NPD6650	Approved
0.6915	Remote Similarity	NPD6098	Approved
0.6909	Remote Similarity	NPD7115	Discovery
0.6907	Remote Similarity	NPD7515	Phase 2
0.6907	Remote Similarity	NPD6411	Approved
0.6887	Remote Similarity	NPD6012	Approved
0.6887	Remote Similarity	NPD6373	Approved
0.6887	Remote Similarity	NPD6013	Approved
0.6887	Remote Similarity	NPD6014	Approved
0.6887	Remote Similarity	NPD6372	Approved
0.6882	Remote Similarity	NPD3665	Phase 1
0.6882	Remote Similarity	NPD3666	Approved
0.6882	Remote Similarity	NPD3133	Approved
0.6875	Remote Similarity	NPD6080	Approved
0.6875	Remote Similarity	NPD6904	Approved
0.6875	Remote Similarity	NPD6673	Approved
0.6869	Remote Similarity	NPD5695	Phase 3
0.6857	Remote Similarity	NPD5701	Approved
0.6832	Remote Similarity	NPD5696	Approved
0.6832	Remote Similarity	NPD7638	Approved
0.6822	Remote Similarity	NPD7290	Approved
0.6822	Remote Similarity	NPD7102	Approved
0.6822	Remote Similarity	NPD6883	Approved
0.6813	Remote Similarity	NPD4695	Discontinued
0.6804	Remote Similarity	NPD5785	Approved
0.6804	Remote Similarity	NPD5692	Phase 3
0.68	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5222	Approved
0.68	Remote Similarity	NPD5221	Approved
0.68	Remote Similarity	NPD4697	Phase 3
0.6792	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD7640	Approved
0.6765	Remote Similarity	NPD7639	Approved
0.6759	Remote Similarity	NPD6869	Approved
0.6759	Remote Similarity	NPD6847	Approved
0.6759	Remote Similarity	NPD6617	Approved
0.6759	Remote Similarity	NPD8130	Phase 1
0.6737	Remote Similarity	NPD5279	Phase 3
0.6735	Remote Similarity	NPD5694	Approved
0.6735	Remote Similarity	NPD6050	Approved
0.6733	Remote Similarity	NPD5173	Approved
0.6733	Remote Similarity	NPD6084	Phase 2
0.6733	Remote Similarity	NPD6083	Phase 2
0.6701	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6101	Approved
0.6701	Remote Similarity	NPD6051	Approved
0.6697	Remote Similarity	NPD6882	Approved
0.6697	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6636	Remote Similarity	NPD6686	Approved
0.6635	Remote Similarity	NPD5211	Phase 2
0.6606	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5286	Approved
0.6602	Remote Similarity	NPD4696	Approved
0.6602	Remote Similarity	NPD5285	Approved
0.6569	Remote Similarity	NPD4755	Approved
0.6566	Remote Similarity	NPD5284	Approved
0.6566	Remote Similarity	NPD5281	Approved
0.6552	Remote Similarity	NPD4691	Approved
0.6542	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5223	Approved
0.6522	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6274	Approved
0.6518	Remote Similarity	NPD6868	Approved
0.6509	Remote Similarity	NPD5141	Approved
0.65	Remote Similarity	NPD4202	Approved
0.6489	Remote Similarity	NPD4221	Approved
0.6489	Remote Similarity	NPD4223	Phase 3
0.6486	Remote Similarity	NPD4632	Approved
0.6476	Remote Similarity	NPD5225	Approved
0.6476	Remote Similarity	NPD4633	Approved
0.6476	Remote Similarity	NPD5224	Approved
0.6476	Remote Similarity	NPD5226	Approved
0.6471	Remote Similarity	NPD7732	Phase 3
0.646	Remote Similarity	NPD6317	Approved
0.6442	Remote Similarity	NPD4700	Approved
0.6437	Remote Similarity	NPD4137	Phase 3
0.6415	Remote Similarity	NPD6052	Approved
0.6415	Remote Similarity	NPD5175	Approved
0.6415	Remote Similarity	NPD5174	Approved
0.6404	Remote Similarity	NPD6313	Approved
0.6404	Remote Similarity	NPD6335	Approved
0.6404	Remote Similarity	NPD6314	Approved
0.64	Remote Similarity	NPD8035	Phase 2
0.64	Remote Similarity	NPD8034	Phase 2
0.6396	Remote Similarity	NPD6053	Discontinued
0.6392	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4623	Approved
0.6392	Remote Similarity	NPD5690	Phase 2
0.6392	Remote Similarity	NPD4519	Discontinued
0.6392	Remote Similarity	NPD6422	Discontinued
0.6392	Remote Similarity	NPD5786	Approved
0.6373	Remote Similarity	NPD5210	Approved
0.6373	Remote Similarity	NPD4629	Approved
0.6373	Remote Similarity	NPD5654	Approved
0.6364	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD4747	Approved
0.6364	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4197	Approved
0.6354	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7100	Approved
0.6348	Remote Similarity	NPD7101	Approved
0.6333	Remote Similarity	NPD4058	Approved
0.6316	Remote Similarity	NPD6009	Approved
0.6316	Remote Similarity	NPD6435	Approved
0.6311	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6698	Approved
0.63	Remote Similarity	NPD46	Approved
0.6293	Remote Similarity	NPD6319	Approved
0.6292	Remote Similarity	NPD5276	Approved
0.6289	Remote Similarity	NPD5329	Approved
0.6289	Remote Similarity	NPD1696	Phase 3
0.6289	Remote Similarity	NPD5363	Approved
0.6289	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD7331	Phase 2
0.6275	Remote Similarity	NPD5282	Discontinued
0.6273	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4754	Approved
0.625	Remote Similarity	NPD7154	Phase 3
0.625	Remote Similarity	NPD5959	Approved
0.6239	Remote Similarity	NPD5983	Phase 2
0.6239	Remote Similarity	NPD6614	Approved
0.6237	Remote Similarity	NPD3617	Approved
0.6237	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4138	Approved
0.6224	Remote Similarity	NPD4689	Approved
0.6224	Remote Similarity	NPD4693	Phase 3
0.6224	Remote Similarity	NPD4694	Approved
0.6224	Remote Similarity	NPD5280	Approved
0.6224	Remote Similarity	NPD4690	Approved
0.6224	Remote Similarity	NPD4688	Approved
0.6224	Remote Similarity	NPD5205	Approved
0.6218	Remote Similarity	NPD7492	Approved
0.6216	Remote Similarity	NPD6371	Approved
0.6211	Remote Similarity	NPD5369	Approved
0.6196	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD4729	Approved
0.6182	Remote Similarity	NPD4730	Approved
0.6182	Remote Similarity	NPD5128	Approved
0.6182	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5168	Approved
0.6179	Remote Similarity	NPD7260	Phase 2
0.6168	Remote Similarity	NPD7632	Discontinued
0.6167	Remote Similarity	NPD6616	Approved
0.6163	Remote Similarity	NPD7341	Phase 2
0.6154	Remote Similarity	NPD5733	Approved
0.6154	Remote Similarity	NPD7614	Phase 1
0.6154	Remote Similarity	NPD4687	Approved
0.6154	Remote Similarity	NPD6054	Approved
0.6147	Remote Similarity	NPD4767	Approved
0.6147	Remote Similarity	NPD4768	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