NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	341.995
LogP:	3.283
LogD:	2.755
LogS:	-4.731
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.836
Synthetic Accessibility Score:	4.371
Fsp3:	0.55
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:	-4.789
MDCK Permeability:	2.5090672352234833e-05
Pgp-inhibitor:	0.486
Pgp-substrate:	0.2
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.392
Plasma Protein Binding (PPB):	89.48397064208984%
Volume Distribution (VD):	0.879
Pgp-substrate:	10.706537246704102%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.349
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.692
CYP3A4-inhibitor:	0.218
CYP3A4-substrate:	0.504

ADMET: Excretion

Clearance (CL):	6.305
Half-life (T1/2):	0.039

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.167
Drug-inuced Liver Injury (DILI):	0.139
AMES Toxicity:	0.264
Rat Oral Acute Toxicity:	0.656
Maximum Recommended Daily Dose:	0.873
Skin Sensitization:	0.354
Carcinogencity:	0.175
Eye Corrosion:	0.004
Eye Irritation:	0.043
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC476645

Natural Product ID:	NPC476645
*Common Name:**	(4R,4aS,10R,10aS)-8-ethenyl-4,10-dihydroxy-1,1,4a,7-tetramethyl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
IUPAC Name:	(4R,4aS,10R,10aS)-8-ethenyl-4,10-dihydroxy-1,1,4a,7-tetramethyl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
Synonyms:	Aspergiloid C
Standard InCHIKey:	XKZQNOQYKJKHNV-FBVAEJEDSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-6-12-11(2)7-8-13-15(12)16(22)17(23)18-19(3,4)10-9-14(21)20(13,18)5/h6-8,14,17-18,21,23H,1,9-10H2,2-5H3/t14-,17+,18+,20+/m1/s1
SMILES:	CC1=C(C2=C(C=C1)[C@]3([C@@H](CCC([C@@H]3[C@H](C2=O)O)(C)C)O)C)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	57333711
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO33649	Aspergillus sp. YXf3	Species	Aspergillaceae	Eukaryota	isolated from a healthy leaf of Ginkgo biloba	the campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	30000	nM	PMID[22196792]

☑ 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 NPC476645 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	222
0.1-0.2	1083
0.2-0.3	2227
0.3-0.4	6507
0.4-0.5	12143
0.5-0.6	14478
0.6-0.7	5318
0.7-0.8	653
0.8-0.85	50
0.85-0.9	13
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9279	High Similarity	NPC471189
0.9018	High Similarity	NPC265513
0.8824	High Similarity	NPC472981
0.8803	High Similarity	NPC222968
0.8803	High Similarity	NPC323440
0.8803	High Similarity	NPC80605
0.8739	High Similarity	NPC471186
0.8707	High Similarity	NPC215419
0.8696	High Similarity	NPC143768
0.8629	High Similarity	NPC478162
0.8629	High Similarity	NPC478165
0.8571	High Similarity	NPC318173
0.8534	High Similarity	NPC470253
0.8516	High Similarity	NPC78307
0.8462	Intermediate Similarity	NPC471721
0.845	Intermediate Similarity	NPC23894
0.8448	Intermediate Similarity	NPC471188
0.843	Intermediate Similarity	NPC183339
0.843	Intermediate Similarity	NPC133389
0.843	Intermediate Similarity	NPC234337
0.8376	Intermediate Similarity	NPC93287
0.8359	Intermediate Similarity	NPC471851
0.8347	Intermediate Similarity	NPC202015
0.8333	Intermediate Similarity	NPC142326
0.8333	Intermediate Similarity	NPC94751
0.8306	Intermediate Similarity	NPC472681
0.8306	Intermediate Similarity	NPC328107
0.8305	Intermediate Similarity	NPC326664
0.8293	Intermediate Similarity	NPC293831
0.8293	Intermediate Similarity	NPC369
0.8291	Intermediate Similarity	NPC292834
0.8261	Intermediate Similarity	NPC112903
0.8258	Intermediate Similarity	NPC475957
0.8189	Intermediate Similarity	NPC115797
0.8189	Intermediate Similarity	NPC51448
0.8174	Intermediate Similarity	NPC100767
0.8174	Intermediate Similarity	NPC185763
0.8174	Intermediate Similarity	NPC83409
0.8168	Intermediate Similarity	NPC474659
0.8168	Intermediate Similarity	NPC202225
0.816	Intermediate Similarity	NPC85511
0.8151	Intermediate Similarity	NPC196673
0.8145	Intermediate Similarity	NPC269923
0.8145	Intermediate Similarity	NPC167323
0.8136	Intermediate Similarity	NPC186128
0.8136	Intermediate Similarity	NPC280789
0.813	Intermediate Similarity	NPC472680
0.813	Intermediate Similarity	NPC472679
0.8108	Intermediate Similarity	NPC324602
0.8099	Intermediate Similarity	NPC469843
0.8092	Intermediate Similarity	NPC126516
0.8092	Intermediate Similarity	NPC310662
0.8087	Intermediate Similarity	NPC172483
0.8077	Intermediate Similarity	NPC476847
0.807	Intermediate Similarity	NPC247976
0.8065	Intermediate Similarity	NPC476234
0.8062	Intermediate Similarity	NPC276238
0.8062	Intermediate Similarity	NPC171460
0.8047	Intermediate Similarity	NPC176130
0.8047	Intermediate Similarity	NPC84672
0.8047	Intermediate Similarity	NPC78364
0.8047	Intermediate Similarity	NPC69424
0.8031	Intermediate Similarity	NPC275576
0.8017	Intermediate Similarity	NPC62138
0.8016	Intermediate Similarity	NPC318067
0.8	Intermediate Similarity	NPC108129
0.7969	Intermediate Similarity	NPC253681
0.7969	Intermediate Similarity	NPC169913
0.7956	Intermediate Similarity	NPC248068
0.7955	Intermediate Similarity	NPC477139
0.7955	Intermediate Similarity	NPC329913
0.7949	Intermediate Similarity	NPC472979
0.7949	Intermediate Similarity	NPC27252
0.7934	Intermediate Similarity	NPC93181
0.7934	Intermediate Similarity	NPC186933
0.7931	Intermediate Similarity	NPC134120
0.7931	Intermediate Similarity	NPC243601
0.7923	Intermediate Similarity	NPC262819
0.7914	Intermediate Similarity	NPC478160
0.7913	Intermediate Similarity	NPC274443
0.7907	Intermediate Similarity	NPC72667
0.7895	Intermediate Similarity	NPC133809
0.7895	Intermediate Similarity	NPC128248
0.7895	Intermediate Similarity	NPC136810
0.7881	Intermediate Similarity	NPC149455
0.7881	Intermediate Similarity	NPC64642
0.7881	Intermediate Similarity	NPC472982
0.7874	Intermediate Similarity	NPC471187
0.7857	Intermediate Similarity	NPC185208
0.7857	Intermediate Similarity	NPC219573
0.7851	Intermediate Similarity	NPC67377
0.7846	Intermediate Similarity	NPC3009
0.7845	Intermediate Similarity	NPC56168
0.7833	Intermediate Similarity	NPC218855
0.7829	Intermediate Similarity	NPC473220
0.7829	Intermediate Similarity	NPC470753
0.7829	Intermediate Similarity	NPC254492
0.7826	Intermediate Similarity	NPC244427
0.7826	Intermediate Similarity	NPC222390
0.7812	Intermediate Similarity	NPC199273
0.7812	Intermediate Similarity	NPC181334
0.781	Intermediate Similarity	NPC471853
0.7805	Intermediate Similarity	NPC212891
0.7797	Intermediate Similarity	NPC472980
0.7797	Intermediate Similarity	NPC211439
0.7788	Intermediate Similarity	NPC239185
0.7786	Intermediate Similarity	NPC303910
0.7786	Intermediate Similarity	NPC49272
0.7778	Intermediate Similarity	NPC471670
0.777	Intermediate Similarity	NPC478164
0.7769	Intermediate Similarity	NPC262936
0.7769	Intermediate Similarity	NPC30491
0.7761	Intermediate Similarity	NPC477893
0.7761	Intermediate Similarity	NPC477896
0.776	Intermediate Similarity	NPC204784
0.7759	Intermediate Similarity	NPC329556
0.7752	Intermediate Similarity	NPC137750
0.7752	Intermediate Similarity	NPC470765
0.775	Intermediate Similarity	NPC474057
0.775	Intermediate Similarity	NPC137315
0.775	Intermediate Similarity	NPC475002
0.775	Intermediate Similarity	NPC95126
0.7739	Intermediate Similarity	NPC225079
0.7739	Intermediate Similarity	NPC476993
0.7734	Intermediate Similarity	NPC12881
0.7734	Intermediate Similarity	NPC140118
0.7727	Intermediate Similarity	NPC471334
0.7724	Intermediate Similarity	NPC9274
0.7719	Intermediate Similarity	NPC134882
0.7712	Intermediate Similarity	NPC37914
0.771	Intermediate Similarity	NPC96024
0.7705	Intermediate Similarity	NPC130591
0.7705	Intermediate Similarity	NPC241851
0.7705	Intermediate Similarity	NPC234637
0.7704	Intermediate Similarity	NPC153088
0.7698	Intermediate Similarity	NPC308572
0.7698	Intermediate Similarity	NPC238861
0.7698	Intermediate Similarity	NPC77000
0.7687	Intermediate Similarity	NPC203486
0.7687	Intermediate Similarity	NPC111845
0.7687	Intermediate Similarity	NPC48929
0.7681	Intermediate Similarity	NPC182869
0.768	Intermediate Similarity	NPC472698
0.768	Intermediate Similarity	NPC472697
0.7674	Intermediate Similarity	NPC295664
0.7664	Intermediate Similarity	NPC476643
0.7658	Intermediate Similarity	NPC220596
0.7656	Intermediate Similarity	NPC182333
0.7656	Intermediate Similarity	NPC65627
0.7656	Intermediate Similarity	NPC273336
0.7652	Intermediate Similarity	NPC221825
0.7647	Intermediate Similarity	NPC203732
0.7643	Intermediate Similarity	NPC127857
0.7642	Intermediate Similarity	NPC221275
0.7634	Intermediate Similarity	NPC472678
0.7632	Intermediate Similarity	NPC265220
0.7623	Intermediate Similarity	NPC471481
0.7623	Intermediate Similarity	NPC469547
0.7619	Intermediate Similarity	NPC472708
0.7615	Intermediate Similarity	NPC328997
0.7615	Intermediate Similarity	NPC123506
0.7615	Intermediate Similarity	NPC87985
0.7615	Intermediate Similarity	NPC294050
0.7607	Intermediate Similarity	NPC19856
0.7606	Intermediate Similarity	NPC60509
0.7606	Intermediate Similarity	NPC81698
0.7606	Intermediate Similarity	NPC250046
0.76	Intermediate Similarity	NPC45794
0.7597	Intermediate Similarity	NPC77691
0.7597	Intermediate Similarity	NPC198014
0.7597	Intermediate Similarity	NPC273683
0.7594	Intermediate Similarity	NPC72915
0.7589	Intermediate Similarity	NPC323420
0.7586	Intermediate Similarity	NPC109514
0.7583	Intermediate Similarity	NPC470252
0.7578	Intermediate Similarity	NPC154696
0.7571	Intermediate Similarity	NPC477209
0.7565	Intermediate Similarity	NPC75724
0.7563	Intermediate Similarity	NPC193640
0.7563	Intermediate Similarity	NPC25385
0.7563	Intermediate Similarity	NPC475905
0.7559	Intermediate Similarity	NPC473243
0.7559	Intermediate Similarity	NPC105709
0.7557	Intermediate Similarity	NPC71610
0.7557	Intermediate Similarity	NPC474106
0.7557	Intermediate Similarity	NPC470648
0.7556	Intermediate Similarity	NPC138472
0.7556	Intermediate Similarity	NPC52407
0.7552	Intermediate Similarity	NPC478163
0.7552	Intermediate Similarity	NPC165260
0.7552	Intermediate Similarity	NPC5568
0.7552	Intermediate Similarity	NPC161239
0.7552	Intermediate Similarity	NPC198455
0.7552	Intermediate Similarity	NPC7095
0.7542	Intermediate Similarity	NPC249067
0.7542	Intermediate Similarity	NPC329282
0.7541	Intermediate Similarity	NPC66208
0.7538	Intermediate Similarity	NPC152525
0.7538	Intermediate Similarity	NPC234890
0.7538	Intermediate Similarity	NPC68756

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 NPC476645 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	835
0.2-0.3	1284
0.3-0.4	2885
0.4-0.5	2368
0.5-0.6	1253
0.6-0.7	262
0.7-0.8	24
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
0.8205	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD5951	Approved
0.7886	Intermediate Similarity	NPD7610	Discontinued
0.7788	Intermediate Similarity	NPD3495	Discontinued
0.777	Intermediate Similarity	NPD7236	Approved
0.7759	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD1929	Approved
0.7759	Intermediate Similarity	NPD1930	Approved
0.7698	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7961	Discontinued
0.7652	Intermediate Similarity	NPD2066	Phase 3
0.7622	Intermediate Similarity	NPD7239	Suspended
0.7581	Intermediate Similarity	NPD3317	Approved
0.7559	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD1237	Approved
0.7519	Intermediate Similarity	NPD7008	Discontinued
0.75	Intermediate Similarity	NPD2629	Approved
0.75	Intermediate Similarity	NPD4879	Approved
0.7402	Intermediate Similarity	NPD7009	Phase 2
0.7388	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6858	Approved
0.7339	Intermediate Similarity	NPD7094	Approved
0.7287	Intermediate Similarity	NPD3019	Approved
0.7281	Intermediate Similarity	NPD1088	Approved
0.7231	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD1932	Approved
0.7155	Intermediate Similarity	NPD1693	Approved
0.7155	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2329	Discontinued
0.7154	Intermediate Similarity	NPD2932	Approved
0.7154	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7057	Phase 3
0.7152	Intermediate Similarity	NPD7058	Phase 2
0.713	Intermediate Similarity	NPD7631	Approved
0.7105	Intermediate Similarity	NPD1086	Approved
0.7105	Intermediate Similarity	NPD1089	Approved
0.7105	Intermediate Similarity	NPD1090	Approved
0.7077	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1201	Approved
0.7043	Intermediate Similarity	NPD7609	Phase 3
0.7025	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD800	Approved
0.7014	Intermediate Similarity	NPD7003	Approved
0.7008	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4878	Approved
0.697	Remote Similarity	NPD3026	Approved
0.697	Remote Similarity	NPD3023	Approved
0.6949	Remote Similarity	NPD1989	Approved
0.6947	Remote Similarity	NPD3024	Approved
0.6947	Remote Similarity	NPD3025	Approved
0.6906	Remote Similarity	NPD6663	Approved
0.6901	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4198	Discontinued
0.6897	Remote Similarity	NPD1239	Approved
0.6892	Remote Similarity	NPD6273	Approved
0.6891	Remote Similarity	NPD1564	Approved
0.6891	Remote Similarity	NPD1565	Approved
0.6891	Remote Similarity	NPD1566	Phase 3
0.6875	Remote Similarity	NPD6010	Discontinued
0.6871	Remote Similarity	NPD8165	Discontinued
0.6871	Remote Similarity	NPD7390	Discontinued
0.687	Remote Similarity	NPD3091	Approved
0.6867	Remote Similarity	NPD7458	Discontinued
0.6866	Remote Similarity	NPD3972	Approved
0.6861	Remote Similarity	NPD5736	Approved
0.6855	Remote Similarity	NPD7799	Discontinued
0.685	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1087	Approved
0.6842	Remote Similarity	NPD650	Approved
0.6838	Remote Similarity	NPD1470	Approved
0.6824	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD2345	Approved
0.6767	Remote Similarity	NPD3095	Discontinued
0.6736	Remote Similarity	NPD5405	Approved
0.6736	Remote Similarity	NPD5406	Approved
0.6736	Remote Similarity	NPD5408	Approved
0.6736	Remote Similarity	NPD5404	Approved
0.6694	Remote Similarity	NPD9495	Approved
0.6693	Remote Similarity	NPD1317	Discontinued
0.6691	Remote Similarity	NPD5157	Phase 1
0.6691	Remote Similarity	NPD5159	Phase 2
0.6691	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2346	Discontinued
0.6689	Remote Similarity	NPD3300	Phase 2
0.6667	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7305	Phase 1
0.6667	Remote Similarity	NPD7714	Approved
0.6667	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD3092	Approved
0.6667	Remote Similarity	NPD7715	Approved
0.6667	Remote Similarity	NPD5222	Approved
0.6645	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4199	Phase 3
0.6642	Remote Similarity	NPD1283	Approved
0.6639	Remote Similarity	NPD5286	Approved
0.6639	Remote Similarity	NPD4696	Approved
0.6639	Remote Similarity	NPD5285	Approved
0.6639	Remote Similarity	NPD1563	Approved
0.6614	Remote Similarity	NPD2182	Approved
0.6613	Remote Similarity	NPD6647	Phase 2
0.6612	Remote Similarity	NPD5173	Approved
0.6612	Remote Similarity	NPD4755	Approved
0.661	Remote Similarity	NPD6079	Approved
0.6594	Remote Similarity	NPD3094	Phase 2
0.6585	Remote Similarity	NPD5223	Approved
0.6583	Remote Similarity	NPD6049	Phase 2
0.6583	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5328	Approved
0.6575	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD1651	Approved
0.656	Remote Similarity	NPD5909	Discontinued
0.6555	Remote Similarity	NPD1508	Approved
0.6554	Remote Similarity	NPD8166	Discontinued
0.6549	Remote Similarity	NPD7713	Phase 3
0.6544	Remote Similarity	NPD6287	Discontinued
0.6538	Remote Similarity	NPD7635	Approved
0.6532	Remote Similarity	NPD5211	Phase 2
0.6532	Remote Similarity	NPD5224	Approved
0.6532	Remote Similarity	NPD5226	Approved
0.6532	Remote Similarity	NPD5225	Approved
0.6532	Remote Similarity	NPD4633	Approved
0.6529	Remote Similarity	NPD4697	Phase 3
0.651	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD5048	Discontinued
0.6504	Remote Similarity	NPD4700	Approved
0.65	Remote Similarity	NPD7084	Phase 3
0.6493	Remote Similarity	NPD7741	Discontinued
0.6491	Remote Similarity	NPD9491	Approved
0.649	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD8368	Discontinued
0.648	Remote Similarity	NPD5175	Approved
0.648	Remote Similarity	NPD5174	Approved
0.648	Remote Similarity	NPD5765	Approved
0.6466	Remote Similarity	NPD3618	Phase 1
0.6466	Remote Similarity	NPD405	Clinical (unspecified phase)
0.646	Remote Similarity	NPD942	Approved
0.6457	Remote Similarity	NPD6685	Approved
0.6452	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5347	Phase 2
0.6441	Remote Similarity	NPD5346	Phase 2
0.6438	Remote Similarity	NPD6959	Discontinued
0.6434	Remote Similarity	NPD2067	Discontinued
0.6429	Remote Similarity	NPD164	Approved
0.6429	Remote Similarity	NPD5141	Approved
0.6429	Remote Similarity	NPD2798	Approved
0.6429	Remote Similarity	NPD3226	Approved
0.6423	Remote Similarity	NPD1281	Approved
0.6423	Remote Similarity	NPD5618	Discontinued
0.6418	Remote Similarity	NPD6065	Approved
0.6414	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6966	Discovery
0.6406	Remote Similarity	NPD2342	Discontinued
0.6403	Remote Similarity	NPD1876	Approved
0.6402	Remote Similarity	NPD5844	Phase 1
0.6397	Remote Similarity	NPD5125	Phase 3
0.6397	Remote Similarity	NPD5305	Approved
0.6397	Remote Similarity	NPD5306	Approved
0.6397	Remote Similarity	NPD5126	Approved
0.6393	Remote Similarity	NPD1843	Approved
0.6391	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD8150	Discontinued
0.6389	Remote Similarity	NPD2979	Phase 3
0.6389	Remote Similarity	NPD4140	Approved
0.6387	Remote Similarity	NPD3672	Approved
0.6387	Remote Similarity	NPD3673	Approved
0.6382	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.638	Remote Similarity	NPD7473	Discontinued
0.6371	Remote Similarity	NPD7798	Approved
0.6369	Remote Similarity	NPD8407	Phase 2
0.6369	Remote Similarity	NPD7819	Suspended
0.6351	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD1471	Phase 3
0.6349	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD4754	Approved
0.6333	Remote Similarity	NPD7515	Phase 2
0.6331	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5697	Approved
0.6327	Remote Similarity	NPD2799	Discontinued
0.6325	Remote Similarity	NPD5279	Phase 3
0.6324	Remote Similarity	NPD1245	Approved
0.6323	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD8032	Phase 2
0.6316	Remote Similarity	NPD8435	Approved
0.6316	Remote Similarity	NPD226	Approved
0.6316	Remote Similarity	NPD4766	Approved
0.6316	Remote Similarity	NPD8361	Approved
0.6316	Remote Similarity	NPD8360	Approved
0.6312	Remote Similarity	NPD4980	Approved
0.6308	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4806	Approved
0.6304	Remote Similarity	NPD4807	Approved
0.6303	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD3528	Clinical (unspecified phase)

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