NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	1.983
LogD:	1.482
LogS:	-3.063
# 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:	4.901
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:	-4.725
MDCK Permeability:	2.7580328605836257e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.128
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.14

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.423
Plasma Protein Binding (PPB):	78.90959167480469%
Volume Distribution (VD):	1.251
Pgp-substrate:	30.753103256225586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.16
CYP1A2-substrate:	0.469
CYP2C19-inhibitor:	0.16
CYP2C19-substrate:	0.773
CYP2C9-inhibitor:	0.196
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.646
CYP3A4-substrate:	0.289

ADMET: Excretion

Clearance (CL):	8.706
Half-life (T1/2):	0.657

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.25
Drug-inuced Liver Injury (DILI):	0.339
AMES Toxicity:	0.288
Rat Oral Acute Toxicity:	0.851
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.438
Carcinogencity:	0.642
Eye Corrosion:	0.329
Eye Irritation:	0.292
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC158488

Natural Product ID:	NPC158488
*Common Name:**	2Alpha-Hydroxyantolactone
IUPAC Name:	(3aR,5S,7S,8aR,9aR)-7-hydroxy-5,8a-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one
Synonyms:	2Alpha-Hydroxyalantolactone; 2Alpha-Hydroxyantolactone
Standard InCHIKey:	FZSKLHDEGWSLTB-ATYMOLOSSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-4-10(16)6-15(3)7-13-11(5-12(8)15)9(2)14(17)18-13/h5,8,10-11,13,16H,2,4,6-7H2,1,3H3/t8-,10-,11+,13+,15+/m0/s1
SMILES:	O[C@H]1C[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:	CHEMBL486020
PubChem CID:	125733
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
NPO32995	pulicaria crispa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3404160]

☑ 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
ED50	1
MIC	1
Others	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.33	ug ml-1	PMID[556315]
NPT168	Cell Line	P388	Mus musculus	T/C	=	123.0	%	PMID[556316]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.0	10'-1 ug/ml	PMID[556316]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.0	ug ml-1	PMID[556316]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.625	ug.mL-1	PMID[556316]

☑ 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 NPC158488 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	158
0.1-0.2	971
0.2-0.3	4131
0.3-0.4	8655
0.4-0.5	13382
0.5-0.6	6552
0.6-0.7	6537
0.7-0.8	2213
0.8-0.85	72
0.85-0.9	16
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC216478
0.9213	High Similarity	NPC250075
0.9205	High Similarity	NPC233345
0.9205	High Similarity	NPC186363
0.908	High Similarity	NPC277771
0.9048	High Similarity	NPC178676
0.8977	High Similarity	NPC116620
0.8901	High Similarity	NPC183012
0.8817	High Similarity	NPC23364
0.8737	High Similarity	NPC273005
0.8737	High Similarity	NPC469606
0.8737	High Similarity	NPC31058
0.8736	High Similarity	NPC110405
0.8721	High Similarity	NPC470948
0.8636	High Similarity	NPC6979
0.8587	High Similarity	NPC57117
0.8587	High Similarity	NPC225474
0.8587	High Similarity	NPC148000
0.8587	High Similarity	NPC469596
0.8571	High Similarity	NPC110496
0.8556	High Similarity	NPC73995
0.8556	High Similarity	NPC50488
0.8556	High Similarity	NPC474396
0.8556	High Similarity	NPC168131
0.8542	High Similarity	NPC58329
0.8539	High Similarity	NPC181103
0.8539	High Similarity	NPC305029
0.8526	High Similarity	NPC47024
0.8523	High Similarity	NPC52628
0.8511	High Similarity	NPC474343
0.8495	Intermediate Similarity	NPC259042
0.8495	Intermediate Similarity	NPC157686
0.8485	Intermediate Similarity	NPC275539
0.8485	Intermediate Similarity	NPC189075
0.8478	Intermediate Similarity	NPC475657
0.8469	Intermediate Similarity	NPC469607
0.8462	Intermediate Similarity	NPC152467
0.8454	Intermediate Similarity	NPC36688
0.8444	Intermediate Similarity	NPC215831
0.8427	Intermediate Similarity	NPC329692
0.8427	Intermediate Similarity	NPC250981
0.8427	Intermediate Similarity	NPC477920
0.8427	Intermediate Similarity	NPC85698
0.8409	Intermediate Similarity	NPC97505
0.8404	Intermediate Similarity	NPC134072
0.8404	Intermediate Similarity	NPC234993
0.8404	Intermediate Similarity	NPC228766
0.8404	Intermediate Similarity	NPC165528
0.8404	Intermediate Similarity	NPC93245
0.8404	Intermediate Similarity	NPC202833
0.8404	Intermediate Similarity	NPC284518
0.8387	Intermediate Similarity	NPC24861
0.837	Intermediate Similarity	NPC72845
0.8353	Intermediate Similarity	NPC35574
0.8333	Intermediate Similarity	NPC175293
0.8333	Intermediate Similarity	NPC470012
0.8316	Intermediate Similarity	NPC473963
0.8316	Intermediate Similarity	NPC91695
0.8316	Intermediate Similarity	NPC70145
0.8298	Intermediate Similarity	NPC90014
0.8295	Intermediate Similarity	NPC22611
0.828	Intermediate Similarity	NPC166346
0.828	Intermediate Similarity	NPC139692
0.8261	Intermediate Similarity	NPC232202
0.8256	Intermediate Similarity	NPC470239
0.8256	Intermediate Similarity	NPC470244
0.8247	Intermediate Similarity	NPC471412
0.8242	Intermediate Similarity	NPC136879
0.8242	Intermediate Similarity	NPC477302
0.8222	Intermediate Similarity	NPC9231
0.8211	Intermediate Similarity	NPC473964
0.8182	Intermediate Similarity	NPC226988
0.8182	Intermediate Similarity	NPC296950
0.8163	Intermediate Similarity	NPC164551
0.8163	Intermediate Similarity	NPC137430
0.8163	Intermediate Similarity	NPC476081
0.8161	Intermediate Similarity	NPC195424
0.8155	Intermediate Similarity	NPC194951
0.8155	Intermediate Similarity	NPC12046
0.8152	Intermediate Similarity	NPC5509
0.8152	Intermediate Similarity	NPC218927
0.8152	Intermediate Similarity	NPC206001
0.8144	Intermediate Similarity	NPC471413
0.8144	Intermediate Similarity	NPC473219
0.8144	Intermediate Similarity	NPC470761
0.8144	Intermediate Similarity	NPC474012
0.8144	Intermediate Similarity	NPC476299
0.8144	Intermediate Similarity	NPC476303
0.8132	Intermediate Similarity	NPC312561
0.8125	Intermediate Similarity	NPC136781
0.8119	Intermediate Similarity	NPC476802
0.8119	Intermediate Similarity	NPC89171
0.8111	Intermediate Similarity	NPC86316
0.8111	Intermediate Similarity	NPC106416
0.81	Intermediate Similarity	NPC127609
0.81	Intermediate Similarity	NPC478208
0.809	Intermediate Similarity	NPC250315
0.8085	Intermediate Similarity	NPC115021
0.8081	Intermediate Similarity	NPC120321
0.8081	Intermediate Similarity	NPC254202
0.8081	Intermediate Similarity	NPC99266
0.8081	Intermediate Similarity	NPC8196
0.8081	Intermediate Similarity	NPC476237
0.8077	Intermediate Similarity	NPC157441
0.8068	Intermediate Similarity	NPC38642
0.8068	Intermediate Similarity	NPC473420
0.8068	Intermediate Similarity	NPC475665
0.8065	Intermediate Similarity	NPC475776
0.8065	Intermediate Similarity	NPC153853
0.8061	Intermediate Similarity	NPC475958
0.8061	Intermediate Similarity	NPC242666
0.8061	Intermediate Similarity	NPC308824
0.8043	Intermediate Similarity	NPC202672
0.8043	Intermediate Similarity	NPC477128
0.8043	Intermediate Similarity	NPC473229
0.8043	Intermediate Similarity	NPC226863
0.8041	Intermediate Similarity	NPC476806
0.8041	Intermediate Similarity	NPC476807
0.8023	Intermediate Similarity	NPC41780
0.8023	Intermediate Similarity	NPC187568
0.8022	Intermediate Similarity	NPC471219
0.8022	Intermediate Similarity	NPC185638
0.8021	Intermediate Similarity	NPC29952
0.8021	Intermediate Similarity	NPC165632
0.8021	Intermediate Similarity	NPC242848
0.8	Intermediate Similarity	NPC474841
0.8	Intermediate Similarity	NPC30486
0.8	Intermediate Similarity	NPC146731
0.8	Intermediate Similarity	NPC473434
0.8	Intermediate Similarity	NPC477129
0.8	Intermediate Similarity	NPC471446
0.8	Intermediate Similarity	NPC258532
0.8	Intermediate Similarity	NPC477130
0.798	Intermediate Similarity	NPC165250
0.798	Intermediate Similarity	NPC162973
0.7979	Intermediate Similarity	NPC49420
0.7979	Intermediate Similarity	NPC472814
0.7979	Intermediate Similarity	NPC473944
0.7979	Intermediate Similarity	NPC477574
0.7979	Intermediate Similarity	NPC177037
0.7978	Intermediate Similarity	NPC186276
0.7961	Intermediate Similarity	NPC5103
0.7959	Intermediate Similarity	NPC472644
0.7959	Intermediate Similarity	NPC476767
0.7957	Intermediate Similarity	NPC194642
0.7957	Intermediate Similarity	NPC295312
0.7938	Intermediate Similarity	NPC253826
0.7938	Intermediate Similarity	NPC73911
0.7921	Intermediate Similarity	NPC102352
0.7921	Intermediate Similarity	NPC252296
0.7917	Intermediate Similarity	NPC316215
0.7912	Intermediate Similarity	NPC177932
0.7912	Intermediate Similarity	NPC65661
0.7912	Intermediate Similarity	NPC476602
0.7905	Intermediate Similarity	NPC25909
0.79	Intermediate Similarity	NPC478057
0.79	Intermediate Similarity	NPC95899
0.79	Intermediate Similarity	NPC69171
0.79	Intermediate Similarity	NPC176883
0.79	Intermediate Similarity	NPC61442
0.79	Intermediate Similarity	NPC159533
0.79	Intermediate Similarity	NPC474165
0.79	Intermediate Similarity	NPC156681
0.79	Intermediate Similarity	NPC159442
0.7895	Intermediate Similarity	NPC99653
0.7895	Intermediate Similarity	NPC63118
0.7895	Intermediate Similarity	NPC147272
0.7895	Intermediate Similarity	NPC49776
0.7895	Intermediate Similarity	NPC470224
0.7895	Intermediate Similarity	NPC474436
0.7889	Intermediate Similarity	NPC194637
0.7879	Intermediate Similarity	NPC97435
0.7879	Intermediate Similarity	NPC81530
0.7879	Intermediate Similarity	NPC111292
0.7879	Intermediate Similarity	NPC303559
0.7872	Intermediate Similarity	NPC51486
0.7872	Intermediate Similarity	NPC212679
0.7872	Intermediate Similarity	NPC220454
0.7872	Intermediate Similarity	NPC232426
0.7872	Intermediate Similarity	NPC281942
0.7872	Intermediate Similarity	NPC310479
0.7872	Intermediate Similarity	NPC221111
0.7872	Intermediate Similarity	NPC469595
0.7872	Intermediate Similarity	NPC280149
0.7872	Intermediate Similarity	NPC182136
0.7865	Intermediate Similarity	NPC209318
0.7865	Intermediate Similarity	NPC223330
0.7864	Intermediate Similarity	NPC478210
0.7864	Intermediate Similarity	NPC474243
0.7857	Intermediate Similarity	NPC159763
0.7857	Intermediate Similarity	NPC478056
0.7857	Intermediate Similarity	NPC278386
0.7857	Intermediate Similarity	NPC234617
0.7857	Intermediate Similarity	NPC473154
0.7857	Intermediate Similarity	NPC124512
0.7857	Intermediate Similarity	NPC124703
0.7849	Intermediate Similarity	NPC91248
0.7843	Intermediate Similarity	NPC230541
0.7843	Intermediate Similarity	NPC144854
0.7843	Intermediate Similarity	NPC3316

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 NPC158488 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	137
0.1-0.2	1276
0.2-0.3	3677
0.3-0.4	2663
0.4-0.5	841
0.5-0.6	299
0.6-0.7	226
0.7-0.8	30
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7912	Intermediate Similarity	NPD1694	Approved
0.7857	Intermediate Similarity	NPD4225	Approved
0.7857	Intermediate Similarity	NPD7638	Approved
0.7778	Intermediate Similarity	NPD7640	Approved
0.7778	Intermediate Similarity	NPD7639	Approved
0.7582	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6399	Phase 3
0.7447	Intermediate Similarity	NPD3618	Phase 1
0.7429	Intermediate Similarity	NPD6686	Approved
0.7391	Intermediate Similarity	NPD3667	Approved
0.7374	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7748	Approved
0.7245	Intermediate Similarity	NPD7515	Phase 2
0.7238	Intermediate Similarity	NPD6008	Approved
0.7234	Intermediate Similarity	NPD4786	Approved
0.7228	Intermediate Similarity	NPD7902	Approved
0.7216	Intermediate Similarity	NPD1695	Approved
0.7207	Intermediate Similarity	NPD7115	Discovery
0.7196	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5778	Approved
0.7172	Intermediate Similarity	NPD5779	Approved
0.7143	Intermediate Similarity	NPD46	Approved
0.7143	Intermediate Similarity	NPD6698	Approved
0.713	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7632	Discontinued
0.7083	Intermediate Similarity	NPD7146	Approved
0.7083	Intermediate Similarity	NPD5330	Approved
0.7083	Intermediate Similarity	NPD6409	Approved
0.7083	Intermediate Similarity	NPD7334	Approved
0.7083	Intermediate Similarity	NPD6684	Approved
0.7083	Intermediate Similarity	NPD7521	Approved
0.7071	Intermediate Similarity	NPD6411	Approved
0.7071	Intermediate Similarity	NPD6079	Approved
0.7053	Intermediate Similarity	NPD3666	Approved
0.7053	Intermediate Similarity	NPD3133	Approved
0.7053	Intermediate Similarity	NPD3665	Phase 1
0.7041	Intermediate Similarity	NPD5328	Approved
0.7009	Intermediate Similarity	NPD5697	Approved
0.697	Remote Similarity	NPD5785	Approved
0.6944	Remote Similarity	NPD6899	Approved
0.6944	Remote Similarity	NPD6881	Approved
0.6944	Remote Similarity	NPD6011	Approved
0.6939	Remote Similarity	NPD6903	Approved
0.6939	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4632	Approved
0.6931	Remote Similarity	NPD7900	Approved
0.6931	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7128	Approved
0.6916	Remote Similarity	NPD5739	Approved
0.6916	Remote Similarity	NPD6675	Approved
0.6916	Remote Similarity	NPD6402	Approved
0.6909	Remote Similarity	NPD6649	Approved
0.6909	Remote Similarity	NPD6650	Approved
0.6907	Remote Similarity	NPD5279	Phase 3
0.6893	Remote Similarity	NPD6083	Phase 2
0.6893	Remote Similarity	NPD6084	Phase 2
0.6881	Remote Similarity	NPD6372	Approved
0.6881	Remote Similarity	NPD6373	Approved
0.6881	Remote Similarity	NPD6012	Approved
0.6881	Remote Similarity	NPD6014	Approved
0.6881	Remote Similarity	NPD6013	Approved
0.6869	Remote Similarity	NPD6101	Approved
0.6869	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5695	Phase 3
0.6852	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5701	Approved
0.6847	Remote Similarity	NPD6053	Discontinued
0.6837	Remote Similarity	NPD3573	Approved
0.6832	Remote Similarity	NPD4202	Approved
0.6827	Remote Similarity	NPD5696	Approved
0.6818	Remote Similarity	NPD7102	Approved
0.6818	Remote Similarity	NPD6883	Approved
0.6818	Remote Similarity	NPD7290	Approved
0.6818	Remote Similarity	NPD6371	Approved
0.6813	Remote Similarity	NPD8039	Approved
0.6809	Remote Similarity	NPD4695	Discontinued
0.6804	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4697	Phase 3
0.6796	Remote Similarity	NPD5221	Approved
0.6796	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5222	Approved
0.6789	Remote Similarity	NPD7320	Approved
0.6768	Remote Similarity	NPD6672	Approved
0.6768	Remote Similarity	NPD5737	Approved
0.6765	Remote Similarity	NPD5282	Discontinued
0.6757	Remote Similarity	NPD6617	Approved
0.6757	Remote Similarity	NPD6869	Approved
0.6757	Remote Similarity	NPD6847	Approved
0.6757	Remote Similarity	NPD8130	Phase 1
0.6754	Remote Similarity	NPD6009	Approved
0.6733	Remote Similarity	NPD8034	Phase 2
0.6733	Remote Similarity	NPD8035	Phase 2
0.6733	Remote Similarity	NPD7637	Suspended
0.6733	Remote Similarity	NPD5693	Phase 1
0.6731	Remote Similarity	NPD5173	Approved
0.6724	Remote Similarity	NPD6319	Approved
0.6701	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD3668	Phase 3
0.6699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5344	Discontinued
0.6697	Remote Similarity	NPD6412	Phase 2
0.6697	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8297	Approved
0.6696	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5983	Phase 2
0.6639	Remote Similarity	NPD7492	Approved
0.6636	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5211	Phase 2
0.6634	Remote Similarity	NPD5207	Approved
0.6634	Remote Similarity	NPD7838	Discovery
0.6607	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5286	Approved
0.6604	Remote Similarity	NPD5285	Approved
0.6604	Remote Similarity	NPD4696	Approved
0.6602	Remote Similarity	NPD6001	Approved
0.6598	Remote Similarity	NPD7154	Phase 3
0.6583	Remote Similarity	NPD7507	Approved
0.6583	Remote Similarity	NPD6616	Approved
0.6581	Remote Similarity	NPD6054	Approved
0.6577	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4755	Approved
0.6569	Remote Similarity	NPD5284	Approved
0.6569	Remote Similarity	NPD5281	Approved
0.6566	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7604	Phase 2
0.6542	Remote Similarity	NPD5223	Approved
0.6538	Remote Similarity	NPD5210	Approved
0.6538	Remote Similarity	NPD4629	Approved
0.6535	Remote Similarity	NPD4753	Phase 2
0.6529	Remote Similarity	NPD7078	Approved
0.6525	Remote Similarity	NPD6015	Approved
0.6525	Remote Similarity	NPD6016	Approved
0.6525	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6274	Approved
0.6522	Remote Similarity	NPD6868	Approved
0.6514	Remote Similarity	NPD5141	Approved
0.6495	Remote Similarity	NPD4223	Phase 3
0.6495	Remote Similarity	NPD4221	Approved
0.6491	Remote Similarity	NPD8133	Approved
0.6481	Remote Similarity	NPD4633	Approved
0.6481	Remote Similarity	NPD5224	Approved
0.6481	Remote Similarity	NPD5225	Approved
0.6481	Remote Similarity	NPD5226	Approved
0.6475	Remote Similarity	NPD7736	Approved
0.6471	Remote Similarity	NPD6370	Approved
0.6471	Remote Similarity	NPD5988	Approved
0.6466	Remote Similarity	NPD6317	Approved
0.6465	Remote Similarity	NPD5363	Approved
0.6465	Remote Similarity	NPD1696	Phase 3
0.6458	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6942	Approved
0.6452	Remote Similarity	NPD7339	Approved
0.6449	Remote Similarity	NPD6648	Approved
0.6449	Remote Similarity	NPD4700	Approved
0.6446	Remote Similarity	NPD6336	Discontinued
0.6441	Remote Similarity	NPD6059	Approved
0.6436	Remote Similarity	NPD5208	Approved
0.6429	Remote Similarity	NPD5362	Discontinued
0.6429	Remote Similarity	NPD6695	Phase 3
0.6423	Remote Similarity	NPD7319	Approved
0.6422	Remote Similarity	NPD5175	Approved
0.6422	Remote Similarity	NPD5174	Approved
0.6421	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD8328	Phase 3
0.641	Remote Similarity	NPD6314	Approved
0.641	Remote Similarity	NPD6335	Approved
0.641	Remote Similarity	NPD6313	Approved
0.6408	Remote Similarity	NPD7983	Approved
0.64	Remote Similarity	NPD4519	Discontinued
0.64	Remote Similarity	NPD4249	Approved
0.64	Remote Similarity	NPD5690	Phase 2
0.64	Remote Similarity	NPD6098	Approved
0.64	Remote Similarity	NPD4623	Approved
0.6393	Remote Similarity	NPD8293	Discontinued
0.6392	Remote Similarity	NPD5369	Approved
0.6387	Remote Similarity	NPD8513	Phase 3
0.6387	Remote Similarity	NPD8517	Approved
0.6387	Remote Similarity	NPD8515	Approved
0.6387	Remote Similarity	NPD8516	Approved
0.6373	Remote Similarity	NPD6904	Approved
0.6373	Remote Similarity	NPD6080	Approved
0.6373	Remote Similarity	NPD6051	Approved
0.6373	Remote Similarity	NPD6673	Approved
0.6373	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4634	Approved
0.6364	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4197	Approved
0.6356	Remote Similarity	NPD7100	Approved
0.6356	Remote Similarity	NPD7101	Approved
0.6354	Remote Similarity	NPD6929	Approved
0.6354	Remote Similarity	NPD7645	Phase 2
0.6337	Remote Similarity	NPD4250	Approved
0.6337	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4251	Approved
0.6327	Remote Similarity	NPD4270	Approved
0.6327	Remote Similarity	NPD4269	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