NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	1.937
LogD:	1.585
LogS:	-3.551
# 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:	4.648
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:	-4.768
MDCK Permeability:	1.9530840290826745e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.098
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	67.58167266845703%
Volume Distribution (VD):	0.938
Pgp-substrate:	33.99150085449219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.095
CYP1A2-substrate:	0.228
CYP2C19-inhibitor:	0.142
CYP2C19-substrate:	0.575
CYP2C9-inhibitor:	0.319
CYP2C9-substrate:	0.235
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.257
CYP3A4-substrate:	0.303

ADMET: Excretion

Clearance (CL):	6.1
Half-life (T1/2):	0.491

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.554
Drug-inuced Liver Injury (DILI):	0.814
AMES Toxicity:	0.197
Rat Oral Acute Toxicity:	0.8
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.375
Carcinogencity:	0.59
Eye Corrosion:	0.145
Eye Irritation:	0.87
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC116620

Natural Product ID:	NPC116620
*Common Name:**	Ivalin
IUPAC Name:	(3aR,4aS,7S,8aR,9aR)-7-hydroxy-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
Synonyms:	Ivalin
Standard InCHIKey:	OVIILQQKQPCQTF-GGAZOKNXSA-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/h10-13,16H,1-2,4-7H2,3H3/t10-,11+,12-,13+,15+/m0/s1
SMILES:	O[C@H]1CC(=C)[C@H]2[C@@](C1)(C)C[C@@H]1[C@H](C2)C(=C)C(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644108
PubChem CID:	65156
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
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	whole plant	Changshou County, Chongqing, China	2008-Aug	PMID[21109433]
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	Whole Plant	n.a.	n.a.	PMID[26394911]
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4637	Inula anatolica	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	6

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	12.5	ug.mL-1	PMID[448195]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	25468.3	nM	PMID[448196]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[448196]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	25480.0	nM	PMID[448196]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	IC50	=	15.4	ug.mL-1	PMID[448197]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	IC50	>	128.0	ug.mL-1	PMID[448197]

☑ 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 NPC116620 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	185
0.1-0.2	1328
0.2-0.3	4663
0.3-0.4	10188
0.4-0.5	11497
0.5-0.6	5978
0.6-0.7	6584
0.7-0.8	2064
0.8-0.85	152
0.85-0.9	29
0.9-0.95	23
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.954	High Similarity	NPC469596
0.954	High Similarity	NPC225474
0.954	High Similarity	NPC148000
0.9524	High Similarity	NPC305029
0.9524	High Similarity	NPC181103
0.9432	High Similarity	NPC157686
0.9432	High Similarity	NPC259042
0.9405	High Similarity	NPC85698
0.9398	High Similarity	NPC97505
0.9326	High Similarity	NPC93245
0.9318	High Similarity	NPC24861
0.9294	High Similarity	NPC175293
0.9222	High Similarity	NPC473963
0.9213	High Similarity	NPC90014
0.9176	High Similarity	NPC9231
0.9176	High Similarity	NPC477920
0.9157	High Similarity	NPC226988
0.9111	High Similarity	NPC473964
0.907	High Similarity	NPC470012
0.9022	High Similarity	NPC47024
0.9011	High Similarity	NPC136781
0.8977	High Similarity	NPC475776
0.8977	High Similarity	NPC158488
0.8953	High Similarity	NPC185638
0.8925	High Similarity	NPC475958
0.8913	High Similarity	NPC216478
0.8913	High Similarity	NPC476806
0.8913	High Similarity	NPC476807
0.8901	High Similarity	NPC284518
0.8901	High Similarity	NPC228766
0.8901	High Similarity	NPC165528
0.8876	High Similarity	NPC233345
0.8876	High Similarity	NPC186363
0.8864	High Similarity	NPC194642
0.881	High Similarity	NPC223330
0.881	High Similarity	NPC209318
0.8778	High Similarity	NPC147272
0.875	High Similarity	NPC277771
0.8737	High Similarity	NPC61442
0.8681	High Similarity	NPC250075
0.8632	High Similarity	NPC164551
0.8605	High Similarity	NPC194637
0.8588	High Similarity	NPC38642
0.8587	High Similarity	NPC183012
0.8587	High Similarity	NPC56369
0.8556	High Similarity	NPC153853
0.8542	High Similarity	NPC72842
0.8526	High Similarity	NPC242666
0.8526	High Similarity	NPC308824
0.8511	High Similarity	NPC473155
0.8506	High Similarity	NPC470011
0.8506	High Similarity	NPC219011
0.8478	Intermediate Similarity	NPC471446
0.8478	Intermediate Similarity	NPC57117
0.8478	Intermediate Similarity	NPC474841
0.8478	Intermediate Similarity	NPC473434
0.8469	Intermediate Similarity	NPC78966
0.8469	Intermediate Similarity	NPC284732
0.8469	Intermediate Similarity	NPC110496
0.8434	Intermediate Similarity	NPC92489
0.8404	Intermediate Similarity	NPC474921
0.8404	Intermediate Similarity	NPC474395
0.8384	Intermediate Similarity	NPC37628
0.8384	Intermediate Similarity	NPC275539
0.8384	Intermediate Similarity	NPC189075
0.837	Intermediate Similarity	NPC199543
0.8353	Intermediate Similarity	NPC263951
0.8351	Intermediate Similarity	NPC36688
0.8351	Intermediate Similarity	NPC156681
0.8351	Intermediate Similarity	NPC99510
0.8333	Intermediate Similarity	NPC111292
0.8333	Intermediate Similarity	NPC471412
0.8316	Intermediate Similarity	NPC78427
0.8316	Intermediate Similarity	NPC23364
0.8316	Intermediate Similarity	NPC16911
0.8315	Intermediate Similarity	NPC250981
0.8315	Intermediate Similarity	NPC6979
0.83	Intermediate Similarity	NPC474243
0.8298	Intermediate Similarity	NPC29410
0.8298	Intermediate Similarity	NPC134072
0.8298	Intermediate Similarity	NPC200054
0.8298	Intermediate Similarity	NPC256227
0.8298	Intermediate Similarity	NPC234993
0.828	Intermediate Similarity	NPC66581
0.828	Intermediate Similarity	NPC47853
0.8265	Intermediate Similarity	NPC283850
0.8261	Intermediate Similarity	NPC72845
0.8261	Intermediate Similarity	NPC198054
0.8247	Intermediate Similarity	NPC469606
0.8247	Intermediate Similarity	NPC273005
0.8247	Intermediate Similarity	NPC476081
0.8247	Intermediate Similarity	NPC31058
0.8242	Intermediate Similarity	NPC50488
0.8242	Intermediate Similarity	NPC474396
0.8242	Intermediate Similarity	NPC73995
0.8229	Intermediate Similarity	NPC287676
0.8229	Intermediate Similarity	NPC471413
0.8229	Intermediate Similarity	NPC476303
0.8211	Intermediate Similarity	NPC474343
0.8191	Intermediate Similarity	NPC98639
0.8191	Intermediate Similarity	NPC470232
0.8182	Intermediate Similarity	NPC469607
0.8182	Intermediate Similarity	NPC470948
0.8182	Intermediate Similarity	NPC243347
0.8172	Intermediate Similarity	NPC139692
0.8163	Intermediate Similarity	NPC221421
0.8163	Intermediate Similarity	NPC120321
0.8163	Intermediate Similarity	NPC476237
0.8152	Intermediate Similarity	NPC152467
0.8144	Intermediate Similarity	NPC289148
0.8144	Intermediate Similarity	NPC52899
0.8144	Intermediate Similarity	NPC163963
0.8132	Intermediate Similarity	NPC50847
0.8132	Intermediate Similarity	NPC215831
0.8125	Intermediate Similarity	NPC89099
0.8125	Intermediate Similarity	NPC38471
0.8125	Intermediate Similarity	NPC162459
0.8125	Intermediate Similarity	NPC98837
0.8125	Intermediate Similarity	NPC20479
0.8125	Intermediate Similarity	NPC38296
0.8125	Intermediate Similarity	NPC28864
0.8125	Intermediate Similarity	NPC471038
0.8111	Intermediate Similarity	NPC329692
0.8111	Intermediate Similarity	NPC56593
0.8105	Intermediate Similarity	NPC29952
0.8105	Intermediate Similarity	NPC329910
0.809	Intermediate Similarity	NPC130966
0.8085	Intermediate Similarity	NPC475118
0.8085	Intermediate Similarity	NPC470385
0.8085	Intermediate Similarity	NPC470386
0.8068	Intermediate Similarity	NPC178676
0.8061	Intermediate Similarity	NPC58329
0.8061	Intermediate Similarity	NPC246736
0.8061	Intermediate Similarity	NPC76866
0.8061	Intermediate Similarity	NPC214946
0.8061	Intermediate Similarity	NPC304832
0.8061	Intermediate Similarity	NPC170615
0.8061	Intermediate Similarity	NPC148628
0.8061	Intermediate Similarity	NPC88203
0.8061	Intermediate Similarity	NPC165250
0.8061	Intermediate Similarity	NPC162973
0.8061	Intermediate Similarity	NPC286519
0.8058	Intermediate Similarity	NPC194951
0.8058	Intermediate Similarity	NPC12046
0.8043	Intermediate Similarity	NPC168131
0.8041	Intermediate Similarity	NPC267921
0.8041	Intermediate Similarity	NPC293866
0.8021	Intermediate Similarity	NPC70145
0.8021	Intermediate Similarity	NPC91695
0.8021	Intermediate Similarity	NPC10864
0.802	Intermediate Similarity	NPC255082
0.8	Intermediate Similarity	NPC476601
0.8	Intermediate Similarity	NPC478208
0.8	Intermediate Similarity	NPC210214
0.8	Intermediate Similarity	NPC52628
0.8	Intermediate Similarity	NPC470229
0.7981	Intermediate Similarity	NPC157441
0.798	Intermediate Similarity	NPC254202
0.798	Intermediate Similarity	NPC87927
0.798	Intermediate Similarity	NPC216114
0.798	Intermediate Similarity	NPC176883
0.7979	Intermediate Similarity	NPC294263
0.7979	Intermediate Similarity	NPC475657
0.7959	Intermediate Similarity	NPC252614
0.7959	Intermediate Similarity	NPC46848
0.7957	Intermediate Similarity	NPC232202
0.7955	Intermediate Similarity	NPC475951
0.7955	Intermediate Similarity	NPC47635
0.7938	Intermediate Similarity	NPC474793
0.7935	Intermediate Similarity	NPC477302
0.7935	Intermediate Similarity	NPC136879
0.7921	Intermediate Similarity	NPC302788
0.7921	Intermediate Similarity	NPC67321
0.7921	Intermediate Similarity	NPC187435
0.7917	Intermediate Similarity	NPC307164
0.7917	Intermediate Similarity	NPC219353
0.7917	Intermediate Similarity	NPC154526
0.7917	Intermediate Similarity	NPC104568
0.7917	Intermediate Similarity	NPC470387
0.7917	Intermediate Similarity	NPC472363
0.7917	Intermediate Similarity	NPC202833
0.7917	Intermediate Similarity	NPC13949
0.7917	Intermediate Similarity	NPC472362
0.7917	Intermediate Similarity	NPC242848
0.7907	Intermediate Similarity	NPC474433
0.79	Intermediate Similarity	NPC477127
0.79	Intermediate Similarity	NPC84928
0.79	Intermediate Similarity	NPC296950
0.79	Intermediate Similarity	NPC474558
0.79	Intermediate Similarity	NPC98603
0.79	Intermediate Similarity	NPC202793
0.7895	Intermediate Similarity	NPC100257
0.7895	Intermediate Similarity	NPC224410
0.7889	Intermediate Similarity	NPC32223
0.7882	Intermediate Similarity	NPC39362
0.7879	Intermediate Similarity	NPC275990
0.7879	Intermediate Similarity	NPC137430
0.7872	Intermediate Similarity	NPC198242
0.7872	Intermediate Similarity	NPC49420
0.7872	Intermediate Similarity	NPC211403

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 NPC116620 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1710
0.2-0.3	3832
0.3-0.4	2263
0.4-0.5	691
0.5-0.6	213
0.6-0.7	218
0.7-0.8	51
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7938	Intermediate Similarity	NPD7638	Approved
0.7857	Intermediate Similarity	NPD7640	Approved
0.7857	Intermediate Similarity	NPD7639	Approved
0.7755	Intermediate Similarity	NPD4225	Approved
0.7609	Intermediate Similarity	NPD1694	Approved
0.7609	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD8034	Phase 2
0.7353	Intermediate Similarity	NPD7632	Discontinued
0.734	Intermediate Similarity	NPD3618	Phase 1
0.7283	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6399	Phase 3
0.7196	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7748	Approved
0.717	Intermediate Similarity	NPD6686	Approved
0.717	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7143	Intermediate Similarity	NPD6008	Approved
0.7129	Intermediate Similarity	NPD7902	Approved
0.7117	Intermediate Similarity	NPD7115	Discovery
0.7097	Intermediate Similarity	NPD3667	Approved
0.7033	Intermediate Similarity	NPD6697	Approved
0.7033	Intermediate Similarity	NPD6115	Approved
0.7033	Intermediate Similarity	NPD6118	Approved
0.7033	Intermediate Similarity	NPD6114	Approved
0.7	Intermediate Similarity	NPD8133	Approved
0.697	Remote Similarity	NPD6079	Approved
0.6947	Remote Similarity	NPD4786	Approved
0.6939	Remote Similarity	NPD5328	Approved
0.6931	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5697	Approved
0.6916	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6011	Approved
0.6852	Remote Similarity	NPD6881	Approved
0.6852	Remote Similarity	NPD6899	Approved
0.6847	Remote Similarity	NPD4632	Approved
0.6842	Remote Similarity	NPD4788	Approved
0.6832	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7900	Approved
0.6822	Remote Similarity	NPD7128	Approved
0.6822	Remote Similarity	NPD5739	Approved
0.6822	Remote Similarity	NPD6675	Approved
0.6822	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD6649	Approved
0.6818	Remote Similarity	NPD6650	Approved
0.6813	Remote Similarity	NPD6117	Approved
0.6804	Remote Similarity	NPD7521	Approved
0.6804	Remote Similarity	NPD7334	Approved
0.6804	Remote Similarity	NPD6684	Approved
0.6804	Remote Similarity	NPD7146	Approved
0.6804	Remote Similarity	NPD6409	Approved
0.6804	Remote Similarity	NPD5330	Approved
0.6789	Remote Similarity	NPD6012	Approved
0.6789	Remote Similarity	NPD6013	Approved
0.6789	Remote Similarity	NPD6372	Approved
0.6789	Remote Similarity	NPD6014	Approved
0.6789	Remote Similarity	NPD6373	Approved
0.6778	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD3665	Phase 1
0.6771	Remote Similarity	NPD3666	Approved
0.6771	Remote Similarity	NPD3133	Approved
0.6768	Remote Similarity	NPD1695	Approved
0.6759	Remote Similarity	NPD5701	Approved
0.6739	Remote Similarity	NPD6116	Phase 1
0.6735	Remote Similarity	NPD3573	Approved
0.6733	Remote Similarity	NPD4202	Approved
0.6727	Remote Similarity	NPD7102	Approved
0.6727	Remote Similarity	NPD7290	Approved
0.6727	Remote Similarity	NPD6883	Approved
0.6703	Remote Similarity	NPD3703	Phase 2
0.6701	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4697	Phase 3
0.6699	Remote Similarity	NPD5222	Approved
0.6699	Remote Similarity	NPD5221	Approved
0.6697	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD7507	Approved
0.6638	Remote Similarity	NPD6319	Approved
0.6636	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5173	Approved
0.6635	Remote Similarity	NPD6083	Phase 2
0.6635	Remote Similarity	NPD6084	Phase 2
0.6607	Remote Similarity	NPD6882	Approved
0.6607	Remote Similarity	NPD8297	Approved
0.6602	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5983	Phase 2
0.6571	Remote Similarity	NPD5696	Approved
0.6569	Remote Similarity	NPD5778	Approved
0.6569	Remote Similarity	NPD5779	Approved
0.6555	Remote Similarity	NPD7492	Approved
0.6542	Remote Similarity	NPD5211	Phase 2
0.6535	Remote Similarity	NPD46	Approved
0.6535	Remote Similarity	NPD6698	Approved
0.6535	Remote Similarity	NPD5785	Approved
0.6518	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5286	Approved
0.6509	Remote Similarity	NPD4696	Approved
0.6509	Remote Similarity	NPD5285	Approved
0.6505	Remote Similarity	NPD6001	Approved
0.65	Remote Similarity	NPD6616	Approved
0.65	Remote Similarity	NPD5737	Approved
0.65	Remote Similarity	NPD6672	Approved
0.6496	Remote Similarity	NPD6054	Approved
0.6476	Remote Similarity	NPD4755	Approved
0.6475	Remote Similarity	NPD7319	Approved
0.6471	Remote Similarity	NPD5693	Phase 1
0.6471	Remote Similarity	NPD7604	Phase 2
0.6471	Remote Similarity	NPD6411	Approved
0.6471	Remote Similarity	NPD7637	Suspended
0.6465	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6053	Discontinued
0.6455	Remote Similarity	NPD6412	Phase 2
0.6449	Remote Similarity	NPD5223	Approved
0.6449	Remote Similarity	NPD5344	Discontinued
0.6446	Remote Similarity	NPD7078	Approved
0.6442	Remote Similarity	NPD5695	Phase 3
0.6441	Remote Similarity	NPD6016	Approved
0.6441	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6921	Approved
0.6441	Remote Similarity	NPD6015	Approved
0.6435	Remote Similarity	NPD6868	Approved
0.6435	Remote Similarity	NPD6274	Approved
0.6429	Remote Similarity	NPD3668	Phase 3
0.6429	Remote Similarity	NPD6371	Approved
0.6422	Remote Similarity	NPD5141	Approved
0.6393	Remote Similarity	NPD7736	Approved
0.6389	Remote Similarity	NPD5226	Approved
0.6389	Remote Similarity	NPD4633	Approved
0.6389	Remote Similarity	NPD5225	Approved
0.6389	Remote Similarity	NPD5224	Approved
0.6387	Remote Similarity	NPD5988	Approved
0.6387	Remote Similarity	NPD6370	Approved
0.6379	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6317	Approved
0.6374	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6336	Discontinued
0.6356	Remote Similarity	NPD6059	Approved
0.6355	Remote Similarity	NPD4700	Approved
0.6354	Remote Similarity	NPD4695	Discontinued
0.6346	Remote Similarity	NPD5282	Discontinued
0.6344	Remote Similarity	NPD3702	Approved
0.6333	Remote Similarity	NPD8328	Phase 3
0.633	Remote Similarity	NPD5174	Approved
0.633	Remote Similarity	NPD5175	Approved
0.6325	Remote Similarity	NPD6335	Approved
0.6325	Remote Similarity	NPD7327	Approved
0.6325	Remote Similarity	NPD6313	Approved
0.6325	Remote Similarity	NPD6314	Approved
0.6325	Remote Similarity	NPD7328	Approved
0.6311	Remote Similarity	NPD8293	Discontinued
0.6306	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8033	Approved
0.63	Remote Similarity	NPD5279	Phase 3
0.6286	Remote Similarity	NPD5210	Approved
0.6286	Remote Similarity	NPD4629	Approved
0.6283	Remote Similarity	NPD4634	Approved
0.6277	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6101	Approved
0.6275	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4753	Phase 2
0.6271	Remote Similarity	NPD7100	Approved
0.6271	Remote Similarity	NPD7516	Approved
0.6271	Remote Similarity	NPD7101	Approved
0.625	Remote Similarity	NPD7645	Phase 2
0.625	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4221	Approved
0.6224	Remote Similarity	NPD4223	Phase 3
0.6218	Remote Similarity	NPD8377	Approved
0.6218	Remote Similarity	NPD8294	Approved
0.6214	Remote Similarity	NPD5207	Approved
0.6204	Remote Similarity	NPD6648	Approved
0.6198	Remote Similarity	NPD6067	Discontinued
0.6196	Remote Similarity	NPD5777	Approved
0.6186	Remote Similarity	NPD7525	Registered
0.6182	Remote Similarity	NPD4754	Approved
0.618	Remote Similarity	NPD4224	Phase 2
0.6176	Remote Similarity	NPD5208	Approved
0.617	Remote Similarity	NPD7339	Approved
0.617	Remote Similarity	NPD6942	Approved
0.6167	Remote Similarity	NPD8296	Approved
0.6167	Remote Similarity	NPD8517	Approved
0.6167	Remote Similarity	NPD8515	Approved
0.6167	Remote Similarity	NPD8378	Approved
0.6167	Remote Similarity	NPD8380	Approved
0.6167	Remote Similarity	NPD8335	Approved
0.6167	Remote Similarity	NPD7503	Approved
0.6167	Remote Similarity	NPD8513	Phase 3
0.6167	Remote Similarity	NPD8379	Approved
0.6167	Remote Similarity	NPD8516	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