NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.12
Volume:	276.044
LogP:	4.435
LogD:	3.489
LogS:	-4.373
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.81
Synthetic Accessibility Score:	2.828
Fsp3:	0.176
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:	-4.989
MDCK Permeability:	1.9860266547766514e-05
Pgp-inhibitor:	0.633
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.912
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.641
Plasma Protein Binding (PPB):	97.20945739746094%
Volume Distribution (VD):	0.66
Pgp-substrate:	1.768272042274475%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.748
CYP2C19-inhibitor:	0.325
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.331
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.884
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.451
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	9.355
Half-life (T1/2):	0.55

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.387
AMES Toxicity:	0.602
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.868
Carcinogencity:	0.181
Eye Corrosion:	0.047
Eye Irritation:	0.967
Respiratory Toxicity:	0.492

Download Data

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

Natural Product: NPC95716

Natural Product ID:	NPC95716
*Common Name:**	Effusol
IUPAC Name:	5-ethenyl-1-methyl-9,10-dihydrophenanthrene-2,7-diol
Synonyms:	NSC-371300
Standard InCHIKey:	GEXAPRXWKRZPCK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O2/c1-3-11-8-13(18)9-12-4-5-14-10(2)16(19)7-6-15(14)17(11)12/h3,6-9,18-19H,1,4-5H2,2H3
SMILES:	C=Cc1cc(cc2CCc3c(C)c(ccc3-c12)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL205119
PubChem CID:	100801
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO40173	Juncus inflexus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808510]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30892891]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1150	Juncus effusus	Species	Juncaceae	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	5
MIC	1
Others	5

Activity Type	# Activity
Individual Protein	7
Organism	3
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	IC50	=	240.0	nM	PMID[491135]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	IC50	=	12.0	nM	PMID[491135]
NPT2981	Individual Protein	dTDP-4-dehydrorhamnose reductase	Mycobacterium tuberculosis	IC50	=	25000.0	nM	PMID[491136]
NPT544	Protein Family	Estrogen receptor	Homo sapiens	Ratio IC50	=	20.0	n.a.	PMID[491135]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	20.0	ug.mL-1	PMID[491136]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Ratio	=	16.0	n.a.	PMID[491137]
NPT665	Individual Protein	Solute carrier family 22 member 6	Homo sapiens	IC50	=	23300.0	nM	PMID[491138]
NPT669	Individual Protein	Solute carrier family 22 member 8	Homo sapiens	Inhibition	>	50.0	%	PMID[491138]
NPT665	Individual Protein	Solute carrier family 22 member 6	Homo sapiens	Inhibition	>	50.0	%	PMID[491138]
NPT669	Individual Protein	Solute carrier family 22 member 8	Homo sapiens	IC50	=	22700.0	nM	PMID[491138]

☑ 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 NPC95716 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	303
0.1-0.2	1984
0.2-0.3	4806
0.3-0.4	12347
0.4-0.5	6330
0.5-0.6	8337
0.6-0.7	6396
0.7-0.8	1755
0.8-0.85	287
0.85-0.9	120
0.9-0.95	26
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9904	High Similarity	NPC46940
0.9623	High Similarity	NPC715
0.9533	High Similarity	NPC195922
0.9519	High Similarity	NPC11554
0.9429	High Similarity	NPC58865
0.9429	High Similarity	NPC314187
0.934	High Similarity	NPC141782
0.9273	High Similarity	NPC299180
0.9259	High Similarity	NPC322239
0.9252	High Similarity	NPC151537
0.9252	High Similarity	NPC260323
0.9252	High Similarity	NPC176279
0.9238	High Similarity	NPC151477
0.9231	High Similarity	NPC138942
0.9223	High Similarity	NPC168829
0.9174	High Similarity	NPC268160
0.9167	High Similarity	NPC250323
0.9159	High Similarity	NPC296683
0.9159	High Similarity	NPC13482
0.9143	High Similarity	NPC271274
0.9135	High Similarity	NPC238696
0.9135	High Similarity	NPC288411
0.9091	High Similarity	NPC192948
0.9091	High Similarity	NPC147179
0.9091	High Similarity	NPC35797
0.9048	High Similarity	NPC117115
0.9009	High Similarity	NPC471668
0.9009	High Similarity	NPC38893
0.9009	High Similarity	NPC261973
0.9009	High Similarity	NPC219112
0.9009	High Similarity	NPC308311
0.9009	High Similarity	NPC477137
0.9009	High Similarity	NPC308828
0.9	High Similarity	NPC249270
0.9	High Similarity	NPC107240
0.8962	High Similarity	NPC54765
0.8962	High Similarity	NPC21594
0.8957	High Similarity	NPC176208
0.8938	High Similarity	NPC176893
0.8929	High Similarity	NPC16030
0.8929	High Similarity	NPC304510
0.8929	High Similarity	NPC172219
0.8929	High Similarity	NPC477136
0.8909	High Similarity	NPC321589
0.8899	High Similarity	NPC77772
0.8899	High Similarity	NPC322753
0.886	High Similarity	NPC103916
0.885	High Similarity	NPC469609
0.885	High Similarity	NPC471671
0.8839	High Similarity	NPC469663
0.8839	High Similarity	NPC92
0.8835	High Similarity	NPC156313
0.8835	High Similarity	NPC32674
0.8807	High Similarity	NPC132720
0.8796	High Similarity	NPC262365
0.8796	High Similarity	NPC95344
0.8772	High Similarity	NPC151197
0.8772	High Similarity	NPC126002
0.8772	High Similarity	NPC469644
0.8772	High Similarity	NPC93071
0.8762	High Similarity	NPC51015
0.875	High Similarity	NPC84999
0.875	High Similarity	NPC246760
0.875	High Similarity	NPC469719
0.8739	High Similarity	NPC317869
0.8739	High Similarity	NPC117846
0.8727	High Similarity	NPC266937
0.8727	High Similarity	NPC470770
0.8727	High Similarity	NPC165770
0.8727	High Similarity	NPC4493
0.8727	High Similarity	NPC225679
0.8727	High Similarity	NPC476632
0.8696	High Similarity	NPC260832
0.8696	High Similarity	NPC135467
0.8679	High Similarity	NPC168393
0.8679	High Similarity	NPC233827
0.8673	High Similarity	NPC141001
0.8667	High Similarity	NPC225506
0.8667	High Similarity	NPC211885
0.8661	High Similarity	NPC471534
0.8654	High Similarity	NPC77492
0.8649	High Similarity	NPC177962
0.8649	High Similarity	NPC43525
0.8649	High Similarity	NPC471179
0.8649	High Similarity	NPC228425
0.8649	High Similarity	NPC62867
0.8644	High Similarity	NPC224342
0.8641	High Similarity	NPC26244
0.8641	High Similarity	NPC274678
0.8636	High Similarity	NPC44732
0.8632	High Similarity	NPC71094
0.8624	High Similarity	NPC233835
0.8621	High Similarity	NPC129176
0.8621	High Similarity	NPC259703
0.8621	High Similarity	NPC32322
0.8598	High Similarity	NPC254965
0.8598	High Similarity	NPC327811
0.8598	High Similarity	NPC272029
0.8596	High Similarity	NPC470760
0.8571	High Similarity	NPC35344
0.8571	High Similarity	NPC263753
0.8571	High Similarity	NPC92730
0.8571	High Similarity	NPC141003
0.8571	High Similarity	NPC122005
0.8571	High Similarity	NPC252821
0.8559	High Similarity	NPC308689
0.8558	High Similarity	NPC82664
0.8558	High Similarity	NPC216520
0.8558	High Similarity	NPC132271
0.8558	High Similarity	NPC473388
0.8558	High Similarity	NPC292730
0.8547	High Similarity	NPC249340
0.8547	High Similarity	NPC162935
0.8547	High Similarity	NPC253627
0.8545	High Similarity	NPC202647
0.8544	High Similarity	NPC76938
0.8544	High Similarity	NPC128062
0.8544	High Similarity	NPC151715
0.8544	High Similarity	NPC245187
0.8532	High Similarity	NPC320439
0.8522	High Similarity	NPC154030
0.8522	High Similarity	NPC48342
0.8522	High Similarity	NPC164649
0.8519	High Similarity	NPC99557
0.8519	High Similarity	NPC219286
0.8509	High Similarity	NPC115808
0.8505	High Similarity	NPC108497
0.85	High Similarity	NPC170485
0.8496	Intermediate Similarity	NPC12656
0.8491	Intermediate Similarity	NPC72729
0.8482	Intermediate Similarity	NPC302371
0.8482	Intermediate Similarity	NPC286222
0.8482	Intermediate Similarity	NPC228988
0.8482	Intermediate Similarity	NPC166995
0.8476	Intermediate Similarity	NPC225464
0.8476	Intermediate Similarity	NPC79241
0.8476	Intermediate Similarity	NPC6597
0.8475	Intermediate Similarity	NPC297057
0.8475	Intermediate Similarity	NPC471794
0.8475	Intermediate Similarity	NPC11250
0.8468	Intermediate Similarity	NPC224870
0.8462	Intermediate Similarity	NPC241001
0.8462	Intermediate Similarity	NPC8392
0.8462	Intermediate Similarity	NPC328504
0.8462	Intermediate Similarity	NPC32714
0.8455	Intermediate Similarity	NPC63698
0.8455	Intermediate Similarity	NPC61885
0.8448	Intermediate Similarity	NPC42657
0.8447	Intermediate Similarity	NPC271440
0.8443	Intermediate Similarity	NPC276238
0.844	Intermediate Similarity	NPC67250
0.8435	Intermediate Similarity	NPC25648
0.8421	Intermediate Similarity	NPC474486
0.8411	Intermediate Similarity	NPC252105
0.8411	Intermediate Similarity	NPC12221
0.8403	Intermediate Similarity	NPC198014
0.8403	Intermediate Similarity	NPC471187
0.8396	Intermediate Similarity	NPC128723
0.8396	Intermediate Similarity	NPC299762
0.8396	Intermediate Similarity	NPC33675
0.8393	Intermediate Similarity	NPC469912
0.8393	Intermediate Similarity	NPC224527
0.839	Intermediate Similarity	NPC237667
0.839	Intermediate Similarity	NPC154696
0.8381	Intermediate Similarity	NPC259512
0.8381	Intermediate Similarity	NPC312132
0.8378	Intermediate Similarity	NPC254833
0.8378	Intermediate Similarity	NPC19808
0.8378	Intermediate Similarity	NPC33728
0.8378	Intermediate Similarity	NPC228343
0.8376	Intermediate Similarity	NPC99734
0.8376	Intermediate Similarity	NPC190501
0.8376	Intermediate Similarity	NPC318552
0.8376	Intermediate Similarity	NPC478121
0.8376	Intermediate Similarity	NPC475245
0.8362	Intermediate Similarity	NPC206
0.8362	Intermediate Similarity	NPC328694
0.8362	Intermediate Similarity	NPC63010
0.8361	Intermediate Similarity	NPC96024
0.8361	Intermediate Similarity	NPC215300
0.835	Intermediate Similarity	NPC204210
0.835	Intermediate Similarity	NPC45040
0.8349	Intermediate Similarity	NPC47284
0.8348	Intermediate Similarity	NPC247858
0.8348	Intermediate Similarity	NPC154511
0.8348	Intermediate Similarity	NPC474387
0.8348	Intermediate Similarity	NPC257540
0.8348	Intermediate Similarity	NPC137496
0.8348	Intermediate Similarity	NPC474358
0.8333	Intermediate Similarity	NPC228503
0.8333	Intermediate Similarity	NPC269212
0.8333	Intermediate Similarity	NPC473137
0.8333	Intermediate Similarity	NPC181334
0.8333	Intermediate Similarity	NPC138248
0.8333	Intermediate Similarity	NPC61685
0.8319	Intermediate Similarity	NPC121168
0.8318	Intermediate Similarity	NPC129373
0.8318	Intermediate Similarity	NPC248396
0.8318	Intermediate Similarity	NPC48730
0.8318	Intermediate Similarity	NPC294741

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 NPC95716 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	1087
0.2-0.3	1074
0.3-0.4	2887
0.4-0.5	1949
0.5-0.6	1224
0.6-0.7	480
0.7-0.8	97
0.8-0.85	15
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9238	High Similarity	NPD2342	Discontinued
0.8991	High Similarity	NPD7635	Approved
0.875	High Similarity	NPD3020	Approved
0.8641	High Similarity	NPD2859	Approved
0.8641	High Similarity	NPD2860	Approved
0.8544	High Similarity	NPD2933	Approved
0.8544	High Similarity	NPD2934	Approved
0.8534	High Similarity	NPD2286	Discontinued
0.8522	High Similarity	NPD3091	Approved
0.8462	Intermediate Similarity	NPD844	Approved
0.8381	Intermediate Similarity	NPD288	Approved
0.8378	Intermediate Similarity	NPD3021	Approved
0.8378	Intermediate Similarity	NPD3022	Approved
0.8376	Intermediate Similarity	NPD4059	Approved
0.8376	Intermediate Similarity	NPD3019	Approved
0.8291	Intermediate Similarity	NPD4093	Discontinued
0.8286	Intermediate Similarity	NPD1809	Phase 2
0.8269	Intermediate Similarity	NPD845	Approved
0.825	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD3092	Approved
0.822	Intermediate Similarity	NPD2932	Approved
0.819	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3095	Discontinued
0.8053	Intermediate Similarity	NPD4750	Phase 3
0.8017	Intermediate Similarity	NPD497	Approved
0.8	Intermediate Similarity	NPD4625	Phase 3
0.7967	Intermediate Similarity	NPD3094	Phase 2
0.7934	Intermediate Similarity	NPD1201	Approved
0.7931	Intermediate Similarity	NPD496	Approved
0.7931	Intermediate Similarity	NPD495	Approved
0.7931	Intermediate Similarity	NPD498	Approved
0.7917	Intermediate Similarity	NPD4626	Approved
0.7909	Intermediate Similarity	NPD940	Approved
0.7909	Intermediate Similarity	NPD846	Approved
0.7881	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD5736	Approved
0.7823	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD1242	Phase 1
0.7778	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD1751	Approved
0.7769	Intermediate Similarity	NPD4589	Approved
0.775	Intermediate Similarity	NPD5304	Approved
0.775	Intermediate Similarity	NPD5303	Approved
0.7739	Intermediate Similarity	NPD1792	Phase 2
0.7717	Intermediate Similarity	NPD5156	Approved
0.7717	Intermediate Similarity	NPD5155	Approved
0.7705	Intermediate Similarity	NPD3026	Approved
0.7705	Intermediate Similarity	NPD3023	Approved
0.7692	Intermediate Similarity	NPD4097	Suspended
0.7686	Intermediate Similarity	NPD1651	Approved
0.7686	Intermediate Similarity	NPD3024	Approved
0.7686	Intermediate Similarity	NPD3025	Approved
0.768	Intermediate Similarity	NPD1470	Approved
0.7679	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4060	Phase 1
0.767	Intermediate Similarity	NPD111	Approved
0.7652	Intermediate Similarity	NPD5404	Approved
0.7652	Intermediate Similarity	NPD5406	Approved
0.7652	Intermediate Similarity	NPD5405	Approved
0.7652	Intermediate Similarity	NPD5408	Approved
0.7638	Intermediate Similarity	NPD2605	Approved
0.7638	Intermediate Similarity	NPD2606	Approved
0.7627	Intermediate Similarity	NPD2229	Approved
0.7627	Intermediate Similarity	NPD2234	Approved
0.7627	Intermediate Similarity	NPD2228	Approved
0.7619	Intermediate Similarity	NPD4624	Approved
0.7607	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1283	Approved
0.7597	Intermediate Similarity	NPD6663	Approved
0.7559	Intermediate Similarity	NPD3637	Approved
0.7559	Intermediate Similarity	NPD3636	Approved
0.7559	Intermediate Similarity	NPD3635	Approved
0.7541	Intermediate Similarity	NPD5691	Approved
0.752	Intermediate Similarity	NPD1669	Approved
0.7519	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2421	Approved
0.7518	Intermediate Similarity	NPD2420	Approved
0.75	Intermediate Similarity	NPD3028	Approved
0.75	Intermediate Similarity	NPD709	Approved
0.75	Intermediate Similarity	NPD3594	Approved
0.75	Intermediate Similarity	NPD6671	Approved
0.75	Intermediate Similarity	NPD3595	Approved
0.748	Intermediate Similarity	NPD2195	Approved
0.748	Intermediate Similarity	NPD2194	Approved
0.7479	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD1444	Approved
0.7478	Intermediate Similarity	NPD1445	Approved
0.7444	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD2861	Phase 2
0.7405	Intermediate Similarity	NPD3620	Phase 2
0.7405	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7390	Discontinued
0.7381	Intermediate Similarity	NPD5327	Phase 3
0.7364	Intermediate Similarity	NPD4908	Phase 1
0.736	Intermediate Similarity	NPD1281	Approved
0.736	Intermediate Similarity	NPD1611	Approved
0.7344	Intermediate Similarity	NPD6584	Phase 3
0.7333	Intermediate Similarity	NPD5283	Phase 1
0.7333	Intermediate Similarity	NPD1398	Phase 1
0.7323	Intermediate Similarity	NPD6696	Suspended
0.7317	Intermediate Similarity	NPD7330	Discontinued
0.7313	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7743	Approved
0.7313	Intermediate Similarity	NPD7742	Approved
0.7299	Intermediate Similarity	NPD7003	Approved
0.7295	Intermediate Similarity	NPD7340	Approved
0.7288	Intermediate Similarity	NPD5451	Approved
0.7273	Intermediate Similarity	NPD4140	Approved
0.7266	Intermediate Similarity	NPD1164	Approved
0.7266	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD7041	Phase 2
0.7244	Intermediate Similarity	NPD4749	Approved
0.7239	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1610	Phase 2
0.7222	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD5735	Approved
0.7217	Intermediate Similarity	NPD9500	Approved
0.7214	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4725	Approved
0.7206	Intermediate Similarity	NPD4726	Approved
0.7206	Intermediate Similarity	NPD4721	Approved
0.72	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD228	Approved
0.7165	Intermediate Similarity	NPD2233	Approved
0.7165	Intermediate Similarity	NPD2232	Approved
0.7165	Intermediate Similarity	NPD2230	Approved
0.7164	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD6353	Approved
0.7154	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7037	Approved
0.7131	Intermediate Similarity	NPD5951	Approved
0.7131	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6583	Phase 3
0.7109	Intermediate Similarity	NPD6582	Phase 2
0.7107	Intermediate Similarity	NPD5535	Approved
0.7101	Intermediate Similarity	NPD3638	Discontinued
0.708	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3845	Phase 1
0.7059	Intermediate Similarity	NPD4108	Discontinued
0.7045	Intermediate Similarity	NPD7095	Approved
0.704	Intermediate Similarity	NPD1548	Phase 1
0.7029	Intermediate Similarity	NPD4257	Approved
0.7029	Intermediate Similarity	NPD4256	Phase 2
0.7015	Intermediate Similarity	NPD2979	Phase 3
0.7009	Intermediate Similarity	NPD9610	Approved
0.7009	Intermediate Similarity	NPD9608	Approved
0.7008	Intermediate Similarity	NPD3143	Discontinued
0.7008	Intermediate Similarity	NPD1981	Approved
0.7008	Intermediate Similarity	NPD1983	Approved
0.7008	Intermediate Similarity	NPD1980	Approved
0.7007	Intermediate Similarity	NPD2935	Discontinued
0.7	Intermediate Similarity	NPD3053	Approved
0.7	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4103	Phase 2
0.7	Intermediate Similarity	NPD3055	Approved
0.7	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1793	Approved
0.6992	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3764	Approved
0.6992	Remote Similarity	NPD1791	Approved
0.6977	Remote Similarity	NPD4659	Approved
0.697	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD9377	Approved
0.6967	Remote Similarity	NPD9379	Approved
0.694	Remote Similarity	NPD6407	Approved
0.694	Remote Similarity	NPD8032	Phase 2
0.694	Remote Similarity	NPD6405	Approved
0.6935	Remote Similarity	NPD6387	Discontinued
0.6929	Remote Similarity	NPD2668	Approved
0.6929	Remote Similarity	NPD8166	Discontinued
0.6929	Remote Similarity	NPD2667	Approved
0.6923	Remote Similarity	NPD5310	Approved
0.6923	Remote Similarity	NPD5311	Approved
0.6917	Remote Similarity	NPD2684	Approved
0.6917	Remote Similarity	NPD3027	Phase 3
0.6912	Remote Similarity	NPD2157	Approved
0.6899	Remote Similarity	NPD3070	Discontinued
0.6897	Remote Similarity	NPD1616	Discontinued
0.6894	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD968	Approved
0.6884	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4476	Approved
0.6884	Remote Similarity	NPD4477	Approved
0.688	Remote Similarity	NPD7636	Approved
0.6875	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2797	Approved
0.687	Remote Similarity	NPD9273	Approved
0.6853	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3444	Approved
0.685	Remote Similarity	NPD3445	Approved
0.685	Remote Similarity	NPD3443	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