NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	382.25
Volume:	419.919
LogP:	5.462
LogD:	4.238
LogS:	-4.746
# Rotatable Bonds:	0
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.652
Synthetic Accessibility Score:	4.463
Fsp3:	0.64
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.066
MDCK Permeability:	2.8212796678417362e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.079
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.867
30% Bioavailability (F30%):	0.475

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.242
Plasma Protein Binding (PPB):	96.11331939697266%
Volume Distribution (VD):	1.174
Pgp-substrate:	3.7185940742492676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.815
CYP2C19-inhibitor:	0.676
CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.719
CYP2C9-substrate:	0.782
CYP2D6-inhibitor:	0.826
CYP2D6-substrate:	0.634
CYP3A4-inhibitor:	0.935
CYP3A4-substrate:	0.672

ADMET: Excretion

Clearance (CL):	15.621
Half-life (T1/2):	0.026

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.677
Maximum Recommended Daily Dose:	0.627
Skin Sensitization:	0.815
Carcinogencity:	0.408
Eye Corrosion:	0.013
Eye Irritation:	0.286
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC476847

Natural Product ID:	NPC476847
*Common Name:**	(1S,11R,12S,17S,18S)-3,18-dihydroxy-1,4,8,12,16,16-hexamethyltetracyclo[9.8.0.02,7.012,17]nonadeca-2(7),3,5,8-tetraen-10-one
IUPAC Name:	(1S,11R,12S,17S,18S)-3,18-dihydroxy-1,4,8,12,16,16-hexamethyltetracyclo[9.8.0.02,7.012,17]nonadeca-2(7),3,5,8-tetraen-10-one
Synonyms:
Standard InCHIKey:	QJOJZCFVMYSSFY-YDEYUWIPSA-N
Standard InCHI:	InChI=1S/C25H34O3/c1-14-8-9-16-15(2)12-17(26)22-24(5)11-7-10-23(3,4)21(24)18(27)13-25(22,6)19(16)20(14)28/h8-9,12,18,21-22,27-28H,7,10-11,13H2,1-6H3/t18-,21-,22+,24-,25+/m0/s1
SMILES:	CC1=C(C2=C(C=C1)C(=CC(=O)[C@H]3[C@@]2(C[C@@H]([C@@H]4[C@@]3(CCCC4(C)C)C)O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118737361
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004647] 1-hydroxy-4-unsubstituted benzenoids

*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
NPO33652	Clathria gombawuiensis	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23799303]
NPO33652	Clathria gombawuiensis	Species	Microcionidae	Eukaryota	n.a.	Gageo-do, Korea, at a depth of 25 m	2006-SEP	PMID[25634623]
NPO33652	Clathria gombawuiensis	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29182331]

☑ 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
MIC	2
Others	2

Activity Type	# Activity
Cell Line	2
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	LC50	=	4700	nM	PMID[25634623]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	5400	nM	PMID[25634623]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100	ug/ml	PMID[25634623]
NPT2	Others	Unspecified		MIC	>	100	ug/ml	PMID[25634623]

☑ 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 NPC476847 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	294
0.1-0.2	1247
0.2-0.3	2361
0.3-0.4	5818
0.4-0.5	10552
0.5-0.6	9833
0.6-0.7	10478
0.7-0.8	1954
0.8-0.85	134
0.85-0.9	25
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9055	High Similarity	NPC87985
0.8976	High Similarity	NPC181334
0.8939	High Similarity	NPC78307
0.8931	High Similarity	NPC471851
0.8898	High Similarity	NPC471187
0.8779	High Similarity	NPC276238
0.8769	High Similarity	NPC84672
0.8769	High Similarity	NPC69424
0.8769	High Similarity	NPC176130
0.8769	High Similarity	NPC78364
0.876	High Similarity	NPC137750
0.875	High Similarity	NPC198014
0.874	High Similarity	NPC154696
0.8731	High Similarity	NPC202225
0.8722	High Similarity	NPC165612
0.8692	High Similarity	NPC71610
0.8676	High Similarity	NPC475957
0.8672	High Similarity	NPC11250
0.8661	High Similarity	NPC259703
0.8661	High Similarity	NPC32322
0.8657	High Similarity	NPC477139
0.8633	High Similarity	NPC248068
0.8626	High Similarity	NPC72667
0.8623	High Similarity	NPC471853
0.8594	High Similarity	NPC253627
0.8583	High Similarity	NPC234337
0.8583	High Similarity	NPC133389
0.8583	High Similarity	NPC183339
0.8571	High Similarity	NPC108129
0.8571	High Similarity	NPC471671
0.8561	High Similarity	NPC3009
0.856	High Similarity	NPC92
0.856	High Similarity	NPC469663
0.855	High Similarity	NPC254492
0.8538	High Similarity	NPC199273
0.8527	High Similarity	NPC176208
0.8519	High Similarity	NPC49742
0.8504	High Similarity	NPC469644
0.8496	Intermediate Similarity	NPC303910
0.8496	Intermediate Similarity	NPC171460
0.8492	Intermediate Similarity	NPC172219
0.8492	Intermediate Similarity	NPC304510
0.8489	Intermediate Similarity	NPC3218
0.8485	Intermediate Similarity	NPC30491
0.8485	Intermediate Similarity	NPC262936
0.845	Intermediate Similarity	NPC369
0.845	Intermediate Similarity	NPC249340
0.845	Intermediate Similarity	NPC162935
0.845	Intermediate Similarity	NPC293831
0.8425	Intermediate Similarity	NPC469609
0.8421	Intermediate Similarity	NPC229894
0.8421	Intermediate Similarity	NPC96024
0.8413	Intermediate Similarity	NPC308311
0.8413	Intermediate Similarity	NPC477137
0.8413	Intermediate Similarity	NPC38893
0.8413	Intermediate Similarity	NPC219112
0.8409	Intermediate Similarity	NPC269598
0.8406	Intermediate Similarity	NPC477592
0.8394	Intermediate Similarity	NPC153088
0.8385	Intermediate Similarity	NPC121168
0.8382	Intermediate Similarity	NPC111845
0.8372	Intermediate Similarity	NPC241001
0.837	Intermediate Similarity	NPC18798
0.837	Intermediate Similarity	NPC291001
0.8369	Intermediate Similarity	NPC308572
0.8369	Intermediate Similarity	NPC474961
0.8369	Intermediate Similarity	NPC477209
0.8358	Intermediate Similarity	NPC117899
0.8358	Intermediate Similarity	NPC131684
0.8346	Intermediate Similarity	NPC477136
0.8333	Intermediate Similarity	NPC147179
0.8333	Intermediate Similarity	NPC192948
0.8333	Intermediate Similarity	NPC35797
0.8322	Intermediate Similarity	NPC478160
0.8321	Intermediate Similarity	NPC270899
0.831	Intermediate Similarity	NPC100242
0.8306	Intermediate Similarity	NPC471188
0.8298	Intermediate Similarity	NPC272907
0.8298	Intermediate Similarity	NPC2681
0.8295	Intermediate Similarity	NPC190501
0.8295	Intermediate Similarity	NPC318552
0.8284	Intermediate Similarity	NPC193203
0.8281	Intermediate Similarity	NPC154030
0.8273	Intermediate Similarity	NPC53001
0.8268	Intermediate Similarity	NPC308828
0.8264	Intermediate Similarity	NPC143685
0.8261	Intermediate Similarity	NPC477596
0.8261	Intermediate Similarity	NPC249272
0.8258	Intermediate Similarity	NPC173978
0.8254	Intermediate Similarity	NPC268160
0.8248	Intermediate Similarity	NPC475627
0.8248	Intermediate Similarity	NPC475346
0.8248	Intermediate Similarity	NPC475457
0.8248	Intermediate Similarity	NPC18982
0.8248	Intermediate Similarity	NPC114183
0.8248	Intermediate Similarity	NPC314048
0.8248	Intermediate Similarity	NPC138472
0.8244	Intermediate Similarity	NPC282577
0.8239	Intermediate Similarity	NPC135524
0.8235	Intermediate Similarity	NPC41847
0.8235	Intermediate Similarity	NPC93015
0.8231	Intermediate Similarity	NPC472981
0.8217	Intermediate Similarity	NPC42657
0.8214	Intermediate Similarity	NPC230811
0.8214	Intermediate Similarity	NPC477593
0.8214	Intermediate Similarity	NPC87723
0.8207	Intermediate Similarity	NPC5568
0.8201	Intermediate Similarity	NPC191976
0.8194	Intermediate Similarity	NPC170055
0.8188	Intermediate Similarity	NPC12070
0.8188	Intermediate Similarity	NPC477594
0.8188	Intermediate Similarity	NPC293454
0.8182	Intermediate Similarity	NPC478164
0.8182	Intermediate Similarity	NPC273683
0.8175	Intermediate Similarity	NPC70622
0.8169	Intermediate Similarity	NPC204045
0.8169	Intermediate Similarity	NPC305845
0.8154	Intermediate Similarity	NPC478121
0.8138	Intermediate Similarity	NPC477208
0.8134	Intermediate Similarity	NPC253681
0.8129	Intermediate Similarity	NPC279463
0.8129	Intermediate Similarity	NPC103082
0.8125	Intermediate Similarity	NPC218866
0.8125	Intermediate Similarity	NPC84568
0.8125	Intermediate Similarity	NPC300684
0.8125	Intermediate Similarity	NPC48130
0.8125	Intermediate Similarity	NPC126707
0.812	Intermediate Similarity	NPC152525
0.812	Intermediate Similarity	NPC12818
0.812	Intermediate Similarity	NPC68756
0.812	Intermediate Similarity	NPC234890
0.812	Intermediate Similarity	NPC74507
0.8116	Intermediate Similarity	NPC115458
0.8116	Intermediate Similarity	NPC52407
0.8112	Intermediate Similarity	NPC85310
0.8106	Intermediate Similarity	NPC471794
0.8106	Intermediate Similarity	NPC71094
0.8106	Intermediate Similarity	NPC478058
0.8102	Intermediate Similarity	NPC72669
0.8102	Intermediate Similarity	NPC474517
0.8099	Intermediate Similarity	NPC172311
0.8099	Intermediate Similarity	NPC181560
0.8099	Intermediate Similarity	NPC169452
0.8095	Intermediate Similarity	NPC228425
0.8092	Intermediate Similarity	NPC328504
0.8088	Intermediate Similarity	NPC206028
0.8077	Intermediate Similarity	NPC473974
0.8077	Intermediate Similarity	NPC31296
0.8077	Intermediate Similarity	NPC258366
0.8077	Intermediate Similarity	NPC476645
0.8077	Intermediate Similarity	NPC79933
0.8074	Intermediate Similarity	NPC471077
0.8071	Intermediate Similarity	NPC315275
0.8065	Intermediate Similarity	NPC64642
0.8065	Intermediate Similarity	NPC472982
0.8065	Intermediate Similarity	NPC149455
0.806	Intermediate Similarity	NPC123506
0.8058	Intermediate Similarity	NPC161964
0.8058	Intermediate Similarity	NPC213122
0.8058	Intermediate Similarity	NPC287604
0.8058	Intermediate Similarity	NPC472262
0.8056	Intermediate Similarity	NPC477207
0.8043	Intermediate Similarity	NPC58685
0.8042	Intermediate Similarity	NPC477595
0.8042	Intermediate Similarity	NPC91019
0.8042	Intermediate Similarity	NPC106519
0.8029	Intermediate Similarity	NPC31799
0.8029	Intermediate Similarity	NPC199253
0.8029	Intermediate Similarity	NPC136588
0.8029	Intermediate Similarity	NPC253488
0.8028	Intermediate Similarity	NPC242994
0.8028	Intermediate Similarity	NPC138099
0.8016	Intermediate Similarity	NPC471189
0.8016	Intermediate Similarity	NPC260323
0.8016	Intermediate Similarity	NPC176279
0.8015	Intermediate Similarity	NPC282923
0.8015	Intermediate Similarity	NPC135467
0.8015	Intermediate Similarity	NPC260832
0.8015	Intermediate Similarity	NPC48248
0.8014	Intermediate Similarity	NPC277559
0.8014	Intermediate Similarity	NPC285122
0.8014	Intermediate Similarity	NPC474991
0.8014	Intermediate Similarity	NPC305060
0.8014	Intermediate Similarity	NPC49911
0.8	Intermediate Similarity	NPC283088
0.8	Intermediate Similarity	NPC471906
0.8	Intermediate Similarity	NPC244691
0.7986	Intermediate Similarity	NPC201297
0.7986	Intermediate Similarity	NPC137649
0.7986	Intermediate Similarity	NPC310662
0.7986	Intermediate Similarity	NPC469520
0.7986	Intermediate Similarity	NPC193555
0.7986	Intermediate Similarity	NPC267205
0.7985	Intermediate Similarity	NPC142956
0.7984	Intermediate Similarity	NPC141001
0.7984	Intermediate Similarity	NPC471668
0.7973	Intermediate Similarity	NPC247219
0.7973	Intermediate Similarity	NPC477221
0.7972	Intermediate Similarity	NPC315578
0.7971	Intermediate Similarity	NPC164295

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 NPC476847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	844
0.2-0.3	1300
0.3-0.4	2642
0.4-0.5	2212
0.5-0.6	1366
0.6-0.7	466
0.7-0.8	38
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8295	Intermediate Similarity	NPD3019	Approved
0.8154	Intermediate Similarity	NPD2932	Approved
0.803	Intermediate Similarity	NPD1201	Approved
0.7971	Intermediate Similarity	NPD6663	Approved
0.7941	Intermediate Similarity	NPD5736	Approved
0.7863	Intermediate Similarity	NPD3091	Approved
0.7817	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1470	Approved
0.7761	Intermediate Similarity	NPD3092	Approved
0.7687	Intermediate Similarity	NPD3023	Approved
0.7687	Intermediate Similarity	NPD3026	Approved
0.7674	Intermediate Similarity	NPD7635	Approved
0.7669	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3025	Approved
0.7669	Intermediate Similarity	NPD3024	Approved
0.7639	Intermediate Similarity	NPD5406	Approved
0.7639	Intermediate Similarity	NPD6100	Approved
0.7639	Intermediate Similarity	NPD6099	Approved
0.7639	Intermediate Similarity	NPD5405	Approved
0.7639	Intermediate Similarity	NPD5404	Approved
0.7639	Intermediate Similarity	NPD5408	Approved
0.7635	Intermediate Similarity	NPD7390	Discontinued
0.7584	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD2342	Discontinued
0.7551	Intermediate Similarity	NPD8166	Discontinued
0.7536	Intermediate Similarity	NPD3094	Phase 2
0.75	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3095	Discontinued
0.7448	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7003	Approved
0.7424	Intermediate Similarity	NPD5951	Approved
0.7386	Intermediate Similarity	NPD7458	Discontinued
0.7351	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1651	Approved
0.7226	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4626	Approved
0.7226	Intermediate Similarity	NPD4059	Approved
0.7214	Intermediate Similarity	NPD1283	Approved
0.72	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4628	Phase 3
0.719	Intermediate Similarity	NPD6273	Approved
0.7185	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7473	Discontinued
0.7176	Intermediate Similarity	NPD4750	Phase 3
0.7161	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6959	Discontinued
0.7133	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD288	Approved
0.7113	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3300	Phase 2
0.7103	Intermediate Similarity	NPD8032	Phase 2
0.7101	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7819	Suspended
0.7083	Intermediate Similarity	NPD7008	Discontinued
0.7071	Intermediate Similarity	NPD3972	Approved
0.7055	Intermediate Similarity	NPD4140	Approved
0.7051	Intermediate Similarity	NPD3226	Approved
0.704	Intermediate Similarity	NPD1809	Phase 2
0.704	Intermediate Similarity	NPD844	Approved
0.7037	Intermediate Similarity	NPD2629	Approved
0.7034	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5691	Approved
0.7021	Intermediate Similarity	NPD1755	Approved
0.7016	Intermediate Similarity	NPD845	Approved
0.7013	Intermediate Similarity	NPD2532	Approved
0.7013	Intermediate Similarity	NPD2534	Approved
0.7013	Intermediate Similarity	NPD2533	Approved
0.7008	Intermediate Similarity	NPD3020	Approved
0.7007	Intermediate Similarity	NPD5735	Approved
0.7	Intermediate Similarity	NPD2346	Discontinued
0.7	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1281	Approved
0.6994	Remote Similarity	NPD6232	Discontinued
0.6993	Remote Similarity	NPD7236	Approved
0.6992	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5844	Phase 1
0.6985	Remote Similarity	NPD3317	Approved
0.6981	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.698	Remote Similarity	NPD651	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7743	Approved
0.698	Remote Similarity	NPD7742	Approved
0.6977	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4097	Suspended
0.6959	Remote Similarity	NPD8150	Discontinued
0.6959	Remote Similarity	NPD1607	Approved
0.6953	Remote Similarity	NPD289	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD943	Approved
0.6939	Remote Similarity	NPD3620	Phase 2
0.6934	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD8127	Discontinued
0.6918	Remote Similarity	NPD3764	Approved
0.6903	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5327	Phase 3
0.6901	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4380	Phase 2
0.6884	Remote Similarity	NPD7610	Discontinued
0.6879	Remote Similarity	NPD7239	Suspended
0.6867	Remote Similarity	NPD1510	Phase 2
0.6857	Remote Similarity	NPD1751	Approved
0.6857	Remote Similarity	NPD1778	Approved
0.6857	Remote Similarity	NPD2286	Discontinued
0.6853	Remote Similarity	NPD6696	Suspended
0.6849	Remote Similarity	NPD4625	Phase 3
0.6846	Remote Similarity	NPD6651	Approved
0.6845	Remote Similarity	NPD4956	Approved
0.6842	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7741	Discontinued
0.6835	Remote Similarity	NPD9545	Approved
0.6831	Remote Similarity	NPD1608	Approved
0.6828	Remote Similarity	NPD4208	Discontinued
0.6825	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2979	Phase 3
0.6824	Remote Similarity	NPD4060	Phase 1
0.6824	Remote Similarity	NPD1240	Approved
0.6821	Remote Similarity	NPD2935	Discontinued
0.6818	Remote Similarity	NPD6190	Approved
0.6813	Remote Similarity	NPD37	Approved
0.6806	Remote Similarity	NPD2797	Approved
0.6806	Remote Similarity	NPD1164	Approved
0.6803	Remote Similarity	NPD3268	Approved
0.6802	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1237	Approved
0.6791	Remote Similarity	NPD3021	Approved
0.6791	Remote Similarity	NPD3022	Approved
0.6786	Remote Similarity	NPD4093	Discontinued
0.6784	Remote Similarity	NPD8313	Approved
0.6784	Remote Similarity	NPD8312	Approved
0.6776	Remote Similarity	NPD5763	Approved
0.6776	Remote Similarity	NPD5762	Approved
0.6776	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2860	Approved
0.6772	Remote Similarity	NPD2859	Approved
0.6767	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7094	Approved
0.6765	Remote Similarity	NPD5039	Approved
0.6765	Remote Similarity	NPD6858	Approved
0.6759	Remote Similarity	NPD2798	Approved
0.6759	Remote Similarity	NPD4624	Approved
0.6755	Remote Similarity	NPD2799	Discontinued
0.6753	Remote Similarity	NPD3400	Discontinued
0.6748	Remote Similarity	NPD7075	Discontinued
0.6744	Remote Similarity	NPD2066	Phase 3
0.6733	Remote Similarity	NPD6353	Approved
0.6732	Remote Similarity	NPD1549	Phase 2
0.6726	Remote Similarity	NPD7177	Discontinued
0.6713	Remote Similarity	NPD4878	Approved
0.6712	Remote Similarity	NPD2861	Phase 2
0.6711	Remote Similarity	NPD2438	Suspended
0.6711	Remote Similarity	NPD4477	Approved
0.6711	Remote Similarity	NPD2796	Approved
0.6711	Remote Similarity	NPD4476	Approved
0.6708	Remote Similarity	NPD1934	Approved
0.6693	Remote Similarity	NPD2934	Approved
0.6693	Remote Similarity	NPD2933	Approved
0.6689	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3638	Discontinued
0.6687	Remote Similarity	NPD4965	Approved
0.6687	Remote Similarity	NPD4967	Phase 2
0.6687	Remote Similarity	NPD7229	Phase 3
0.6687	Remote Similarity	NPD4966	Approved
0.6686	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5035	Approved
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD2605	Approved
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2606	Approved
0.6667	Remote Similarity	NPD6004	Phase 3
0.6667	Remote Similarity	NPD5760	Phase 2
0.6647	Remote Similarity	NPD5190	Phase 2
0.6646	Remote Similarity	NPD7411	Suspended
0.6645	Remote Similarity	NPD7033	Discontinued
0.6645	Remote Similarity	NPD3750	Approved
0.6645	Remote Similarity	NPD7305	Phase 1
0.6644	Remote Similarity	NPD7715	Approved
0.6644	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7714	Approved
0.6641	Remote Similarity	NPD940	Approved
0.6641	Remote Similarity	NPD846	Approved
0.6629	Remote Similarity	NPD6534	Approved
0.6629	Remote Similarity	NPD6535	Approved
0.6624	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5156	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