NPASS Compound

Structure

CID147179 OpenBabel06191715522D 22 24 0 0 1 0 0 0 0 0999 V2000 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 9 1 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 1 0 0 0 17 19 1 0 0 0 0 17 22 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	4.861
LogD:	4.264
LogS:	-4.044
# 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:	0.801
Synthetic Accessibility Score:	3.63
Fsp3:	0.7
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:	-4.77
MDCK Permeability:	1.9696637536981143e-05
Pgp-inhibitor:	0.948
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.288
Plasma Protein Binding (PPB):	96.69266510009766%
Volume Distribution (VD):	1.779
Pgp-substrate:	3.5472240447998047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.182
CYP1A2-substrate:	0.809
CYP2C19-inhibitor:	0.223
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.27
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.27
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.173
CYP3A4-substrate:	0.503

ADMET: Excretion

Clearance (CL):	10.382
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.835
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.768
Carcinogencity:	0.033
Eye Corrosion:	0.007
Eye Irritation:	0.494
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC147179

Natural Product ID:	NPC147179
*Common Name:**	Totaradiol
IUPAC Name:	(2S,4aS,10aR)-1,1,4a-trimethyl-8-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-2,7-diol
Synonyms:	Totaradiol
Standard InCHIKey:	NORGIWDZGWMMGU-ABSDTBQOSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-12(2)18-13-6-9-16-19(3,4)17(22)10-11-20(16,5)14(13)7-8-15(18)21/h7-8,12,16-17,21-22H,6,9-11H2,1-5H3/t16-,17-,20+/m0/s1
SMILES:	CC(C)c1c2CC[C@H]3C(C)(C)[C@H](CC[C@]3(C)c2ccc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446064
PubChem CID:	9995105
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
NPO5234	Myrica nagi	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5234	Myrica nagi	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5234	Myrica nagi	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5234	Myrica nagi	Species	Myricaceae	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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	25.0	ug.mL-1	PMID[569911]
NPT2539	Organism	Corynebacterium ammoniagenes	Corynebacterium ammoniagenes	MIC	=	100.0	ug.mL-1	PMID[569911]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[569911]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	200.0	ug.mL-1	PMID[569911]
NPT167	Organism	Propionibacterium acnes	Propionibacterium acnes	MIC	=	25.0	ug.mL-1	PMID[569911]

☑ 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 NPC147179 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	277
0.1-0.2	1444
0.2-0.3	3155
0.3-0.4	9244
0.4-0.5	10172
0.5-0.6	10096
0.6-0.7	6594
0.7-0.8	1457
0.8-0.85	152
0.85-0.9	64
0.9-0.95	23
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC268160
0.9907	High Similarity	NPC219112
0.9907	High Similarity	NPC308828
0.9727	High Similarity	NPC469609
0.9725	High Similarity	NPC38893
0.9725	High Similarity	NPC477137
0.9725	High Similarity	NPC308311
0.9636	High Similarity	NPC477136
0.9633	High Similarity	NPC192948
0.9633	High Similarity	NPC35797
0.955	High Similarity	NPC471671
0.9545	High Similarity	NPC469663
0.9545	High Similarity	NPC92
0.9533	High Similarity	NPC141782
0.9464	High Similarity	NPC469644
0.9459	High Similarity	NPC304510
0.9459	High Similarity	NPC172219
0.9381	High Similarity	NPC260832
0.9381	High Similarity	NPC135467
0.9358	High Similarity	NPC228425
0.9304	High Similarity	NPC471794
0.9266	High Similarity	NPC176279
0.9266	High Similarity	NPC260323
0.9204	High Similarity	NPC48342
0.9204	High Similarity	NPC164649
0.9204	High Similarity	NPC154030
0.9189	High Similarity	NPC195922
0.9182	High Similarity	NPC250323
0.9174	High Similarity	NPC13482
0.913	High Similarity	NPC328504
0.9115	High Similarity	NPC16030
0.9091	High Similarity	NPC95716
0.9068	High Similarity	NPC87985
0.906	High Similarity	NPC198014
0.9052	High Similarity	NPC253627
0.9027	High Similarity	NPC257540
0.9027	High Similarity	NPC471668
0.9027	High Similarity	NPC247858
0.9027	High Similarity	NPC474358
0.9027	High Similarity	NPC137496
0.9027	High Similarity	NPC474387
0.9027	High Similarity	NPC154511
0.9009	High Similarity	NPC46940
0.9	High Similarity	NPC132720
0.8991	High Similarity	NPC11554
0.8983	High Similarity	NPC181334
0.8929	High Similarity	NPC715
0.8919	High Similarity	NPC322753
0.8919	High Similarity	NPC77772
0.8899	High Similarity	NPC151477
0.8898	High Similarity	NPC471187
0.8889	High Similarity	NPC77569
0.8889	High Similarity	NPC142198
0.885	High Similarity	NPC471534
0.8814	High Similarity	NPC152946
0.8814	High Similarity	NPC11250
0.8793	High Similarity	NPC151197
0.8793	High Similarity	NPC93071
0.8793	High Similarity	NPC126002
0.8772	High Similarity	NPC469719
0.876	High Similarity	NPC471077
0.875	High Similarity	NPC470770
0.875	High Similarity	NPC4286
0.875	High Similarity	NPC266937
0.875	High Similarity	NPC76119
0.8739	High Similarity	NPC58865
0.8727	High Similarity	NPC472979
0.8727	High Similarity	NPC27252
0.8718	High Similarity	NPC68339
0.8716	High Similarity	NPC117115
0.8716	High Similarity	NPC243601
0.8696	High Similarity	NPC141001
0.8678	High Similarity	NPC325294
0.8678	High Similarity	NPC321822
0.8678	High Similarity	NPC71610
0.8673	High Similarity	NPC62867
0.8673	High Similarity	NPC177962
0.8655	High Similarity	NPC478058
0.8655	High Similarity	NPC321402
0.8655	High Similarity	NPC71094
0.8649	High Similarity	NPC149455
0.8649	High Similarity	NPC64642
0.8649	High Similarity	NPC472982
0.8649	High Similarity	NPC262365
0.8644	High Similarity	NPC259703
0.8644	High Similarity	NPC32322
0.8636	High Similarity	NPC271274
0.8636	High Similarity	NPC21594
0.8632	High Similarity	NPC323074
0.8609	High Similarity	NPC474486
0.8595	High Similarity	NPC124030
0.8595	High Similarity	NPC137750
0.8584	High Similarity	NPC151537
0.8571	High Similarity	NPC162935
0.8571	High Similarity	NPC475166
0.8571	High Similarity	NPC314187
0.8571	High Similarity	NPC249340
0.8559	High Similarity	NPC472980
0.8559	High Similarity	NPC320439
0.8559	High Similarity	NPC318581
0.8559	High Similarity	NPC477037
0.8559	High Similarity	NPC325544
0.8525	High Similarity	NPC100414
0.8525	High Similarity	NPC43000
0.8519	High Similarity	NPC211885
0.8519	High Similarity	NPC225506
0.8509	High Similarity	NPC302371
0.85	High Similarity	NPC176208
0.85	High Similarity	NPC121168
0.8496	Intermediate Similarity	NPC296683
0.8496	Intermediate Similarity	NPC44732
0.8487	Intermediate Similarity	NPC241001
0.8475	Intermediate Similarity	NPC42657
0.8462	Intermediate Similarity	NPC299180
0.8455	Intermediate Similarity	NPC30491
0.8455	Intermediate Similarity	NPC262936
0.8455	Intermediate Similarity	NPC108164
0.8455	Intermediate Similarity	NPC186889
0.8455	Intermediate Similarity	NPC476536
0.8455	Intermediate Similarity	NPC475225
0.8435	Intermediate Similarity	NPC322239
0.8435	Intermediate Similarity	NPC317869
0.8426	Intermediate Similarity	NPC128723
0.8426	Intermediate Similarity	NPC122005
0.8426	Intermediate Similarity	NPC252821
0.8421	Intermediate Similarity	NPC308689
0.8417	Intermediate Similarity	NPC154696
0.8403	Intermediate Similarity	NPC99734
0.8403	Intermediate Similarity	NPC318552
0.8403	Intermediate Similarity	NPC190501
0.839	Intermediate Similarity	NPC206
0.8378	Intermediate Similarity	NPC138942
0.8364	Intermediate Similarity	NPC235762
0.8364	Intermediate Similarity	NPC471228
0.8364	Intermediate Similarity	NPC168829
0.8364	Intermediate Similarity	NPC19856
0.8362	Intermediate Similarity	NPC12656
0.8362	Intermediate Similarity	NPC107240
0.8349	Intermediate Similarity	NPC294741
0.8348	Intermediate Similarity	NPC473521
0.8348	Intermediate Similarity	NPC471179
0.8346	Intermediate Similarity	NPC78307
0.8333	Intermediate Similarity	NPC471851
0.8333	Intermediate Similarity	NPC476847
0.8333	Intermediate Similarity	NPC312341
0.8333	Intermediate Similarity	NPC77492
0.8291	Intermediate Similarity	NPC84999
0.8291	Intermediate Similarity	NPC246760
0.8288	Intermediate Similarity	NPC323810
0.8288	Intermediate Similarity	NPC288411
0.8288	Intermediate Similarity	NPC238696
0.8273	Intermediate Similarity	NPC51015
0.8273	Intermediate Similarity	NPC252105
0.8268	Intermediate Similarity	NPC85595
0.8268	Intermediate Similarity	NPC321086
0.8257	Intermediate Similarity	NPC78119
0.8257	Intermediate Similarity	NPC299762
0.8257	Intermediate Similarity	NPC132078
0.8257	Intermediate Similarity	NPC51333
0.8257	Intermediate Similarity	NPC92730
0.8257	Intermediate Similarity	NPC216468
0.8257	Intermediate Similarity	NPC33675
0.8254	Intermediate Similarity	NPC196193
0.825	Intermediate Similarity	NPC103916
0.825	Intermediate Similarity	NPC478121
0.823	Intermediate Similarity	NPC66834
0.822	Intermediate Similarity	NPC261973
0.822	Intermediate Similarity	NPC312105
0.8217	Intermediate Similarity	NPC103082
0.8214	Intermediate Similarity	NPC219286
0.8214	Intermediate Similarity	NPC47284
0.8214	Intermediate Similarity	NPC471350
0.8214	Intermediate Similarity	NPC99557
0.8211	Intermediate Similarity	NPC265413
0.8211	Intermediate Similarity	NPC10154
0.8205	Intermediate Similarity	NPC473137
0.8205	Intermediate Similarity	NPC249270
0.8203	Intermediate Similarity	NPC227719
0.8198	Intermediate Similarity	NPC269212
0.8197	Intermediate Similarity	NPC297057
0.8182	Intermediate Similarity	NPC72729
0.8182	Intermediate Similarity	NPC174911
0.8182	Intermediate Similarity	NPC129176
0.8182	Intermediate Similarity	NPC213730
0.8175	Intermediate Similarity	NPC276238
0.8167	Intermediate Similarity	NPC176893
0.8165	Intermediate Similarity	NPC474073
0.8165	Intermediate Similarity	NPC79241
0.8165	Intermediate Similarity	NPC225464
0.8165	Intermediate Similarity	NPC6597
0.816	Intermediate Similarity	NPC78364
0.816	Intermediate Similarity	NPC176130
0.816	Intermediate Similarity	NPC69424
0.816	Intermediate Similarity	NPC84672
0.8148	Intermediate Similarity	NPC222146
0.8148	Intermediate Similarity	NPC144682
0.8148	Intermediate Similarity	NPC8392
0.8142	Intermediate Similarity	NPC53740
0.8142	Intermediate Similarity	NPC54765
0.8142	Intermediate Similarity	NPC155072

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 NPC147179 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	919
0.2-0.3	1329
0.3-0.4	2807
0.4-0.5	2043
0.5-0.6	1232
0.6-0.7	451
0.7-0.8	87
0.8-0.85	10
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9204	High Similarity	NPD3091	Approved
0.8889	High Similarity	NPD3092	Approved
0.8718	High Similarity	NPD3095	Discontinued
0.8595	High Similarity	NPD3094	Phase 2
0.8403	Intermediate Similarity	NPD4059	Approved
0.8403	Intermediate Similarity	NPD3019	Approved
0.8393	Intermediate Similarity	NPD2342	Discontinued
0.8348	Intermediate Similarity	NPD7635	Approved
0.8306	Intermediate Similarity	NPD5736	Approved
0.8257	Intermediate Similarity	NPD3020	Approved
0.825	Intermediate Similarity	NPD2932	Approved
0.8148	Intermediate Similarity	NPD1809	Phase 2
0.8073	Intermediate Similarity	NPD288	Approved
0.8056	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6663	Approved
0.8018	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD3620	Phase 2
0.7982	Intermediate Similarity	NPD844	Approved
0.7982	Intermediate Similarity	NPD2859	Approved
0.7982	Intermediate Similarity	NPD2860	Approved
0.7963	Intermediate Similarity	NPD845	Approved
0.7931	Intermediate Similarity	NPD3022	Approved
0.7931	Intermediate Similarity	NPD3021	Approved
0.789	Intermediate Similarity	NPD2934	Approved
0.789	Intermediate Similarity	NPD2933	Approved
0.7879	Intermediate Similarity	NPD7742	Approved
0.7879	Intermediate Similarity	NPD7743	Approved
0.7869	Intermediate Similarity	NPD4093	Discontinued
0.7863	Intermediate Similarity	NPD4097	Suspended
0.7846	Intermediate Similarity	NPD4140	Approved
0.784	Intermediate Similarity	NPD5327	Phase 3
0.7823	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD2286	Discontinued
0.7805	Intermediate Similarity	NPD1751	Approved
0.7797	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD4624	Approved
0.7786	Intermediate Similarity	NPD5735	Approved
0.7778	Intermediate Similarity	NPD4750	Phase 3
0.7742	Intermediate Similarity	NPD3023	Approved
0.7742	Intermediate Similarity	NPD3026	Approved
0.7724	Intermediate Similarity	NPD3024	Approved
0.7724	Intermediate Similarity	NPD3025	Approved
0.7719	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD2606	Approved
0.7674	Intermediate Similarity	NPD2605	Approved
0.7667	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4626	Approved
0.7647	Intermediate Similarity	NPD3638	Discontinued
0.7615	Intermediate Similarity	NPD5155	Approved
0.7615	Intermediate Similarity	NPD5156	Approved
0.7597	Intermediate Similarity	NPD3636	Approved
0.7597	Intermediate Similarity	NPD3635	Approved
0.7597	Intermediate Similarity	NPD3637	Approved
0.7594	Intermediate Similarity	NPD6353	Approved
0.7576	Intermediate Similarity	NPD4060	Phase 1
0.7538	Intermediate Similarity	NPD3595	Approved
0.7538	Intermediate Similarity	NPD3594	Approved
0.7536	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD4589	Approved
0.7519	Intermediate Similarity	NPD2194	Approved
0.7519	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD2195	Approved
0.748	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD1792	Phase 2
0.7478	Intermediate Similarity	NPD846	Approved
0.7478	Intermediate Similarity	NPD940	Approved
0.7462	Intermediate Similarity	NPD2861	Phase 2
0.744	Intermediate Similarity	NPD5691	Approved
0.7424	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD1201	Approved
0.7381	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD2228	Approved
0.7377	Intermediate Similarity	NPD2229	Approved
0.7377	Intermediate Similarity	NPD2234	Approved
0.7364	Intermediate Similarity	NPD6696	Suspended
0.736	Intermediate Similarity	NPD5304	Approved
0.736	Intermediate Similarity	NPD5303	Approved
0.7348	Intermediate Similarity	NPD4625	Phase 3
0.7317	Intermediate Similarity	NPD497	Approved
0.7308	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7041	Phase 2
0.7305	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7266	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3645	Discontinued
0.7254	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4726	Approved
0.7246	Intermediate Similarity	NPD4725	Approved
0.7246	Intermediate Similarity	NPD4721	Approved
0.7241	Intermediate Similarity	NPD1242	Phase 1
0.7236	Intermediate Similarity	NPD496	Approved
0.7236	Intermediate Similarity	NPD495	Approved
0.7236	Intermediate Similarity	NPD498	Approved
0.7231	Intermediate Similarity	NPD1283	Approved
0.7227	Intermediate Similarity	NPD1445	Approved
0.7227	Intermediate Similarity	NPD1444	Approved
0.7222	Intermediate Similarity	NPD111	Approved
0.7222	Intermediate Similarity	NPD7741	Discontinued
0.7222	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7003	Approved
0.7214	Intermediate Similarity	NPD8166	Discontinued
0.72	Intermediate Similarity	NPD7340	Approved
0.7176	Intermediate Similarity	NPD1470	Approved
0.7165	Intermediate Similarity	NPD1651	Approved
0.7154	Intermediate Similarity	NPD4659	Approved
0.7132	Intermediate Similarity	NPD1610	Phase 2
0.7132	Intermediate Similarity	NPD3657	Discovery
0.7121	Intermediate Similarity	NPD6584	Phase 3
0.712	Intermediate Similarity	NPD6671	Approved
0.712	Intermediate Similarity	NPD7157	Approved
0.7101	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD8651	Approved
0.7097	Intermediate Similarity	NPD1398	Phase 1
0.7097	Intermediate Similarity	NPD5283	Phase 1
0.7087	Intermediate Similarity	NPD7330	Discontinued
0.7083	Intermediate Similarity	NPD6273	Approved
0.7077	Intermediate Similarity	NPD2233	Approved
0.7077	Intermediate Similarity	NPD2230	Approved
0.7077	Intermediate Similarity	NPD2232	Approved
0.7071	Intermediate Similarity	NPD7037	Approved
0.7059	Intermediate Similarity	NPD2238	Phase 2
0.705	Intermediate Similarity	NPD5405	Approved
0.705	Intermediate Similarity	NPD5404	Approved
0.705	Intermediate Similarity	NPD5406	Approved
0.705	Intermediate Similarity	NPD5408	Approved
0.7045	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4103	Phase 2
0.7042	Intermediate Similarity	NPD8131	Suspended
0.7034	Intermediate Similarity	NPD5699	Approved
0.7031	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1669	Approved
0.7023	Intermediate Similarity	NPD4749	Approved
0.7021	Intermediate Similarity	NPD6674	Discontinued
0.7014	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD5763	Approved
0.7	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1281	Approved
0.6985	Remote Similarity	NPD8032	Phase 2
0.6985	Remote Similarity	NPD6405	Approved
0.6985	Remote Similarity	NPD6407	Approved
0.6978	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2684	Approved
0.6963	Remote Similarity	NPD3027	Phase 3
0.6957	Remote Similarity	NPD2157	Approved
0.6957	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3028	Approved
0.6944	Remote Similarity	NPD2420	Approved
0.6944	Remote Similarity	NPD2421	Approved
0.694	Remote Similarity	NPD4208	Discontinued
0.6935	Remote Similarity	NPD228	Approved
0.6934	Remote Similarity	NPD3109	Approved
0.6934	Remote Similarity	NPD3110	Approved
0.6923	Remote Similarity	NPD3143	Discontinued
0.6917	Remote Similarity	NPD1129	Approved
0.6917	Remote Similarity	NPD1133	Approved
0.6917	Remote Similarity	NPD1134	Approved
0.6917	Remote Similarity	NPD1131	Approved
0.6917	Remote Similarity	NPD1135	Approved
0.6912	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5451	Approved
0.6911	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2629	Approved
0.6905	Remote Similarity	NPD9614	Approved
0.6905	Remote Similarity	NPD1793	Approved
0.6905	Remote Similarity	NPD1791	Approved
0.6905	Remote Similarity	NPD9618	Approved
0.6905	Remote Similarity	NPD5951	Approved
0.6899	Remote Similarity	NPD1357	Approved
0.6894	Remote Similarity	NPD6583	Phase 3
0.6894	Remote Similarity	NPD6582	Phase 2
0.6857	Remote Similarity	NPD4108	Discontinued
0.6857	Remote Similarity	NPD1753	Discontinued
0.685	Remote Similarity	NPD709	Approved
0.6846	Remote Similarity	NPD7725	Approved
0.6846	Remote Similarity	NPD2668	Approved
0.6846	Remote Similarity	NPD2667	Approved
0.6838	Remote Similarity	NPD7095	Approved
0.6833	Remote Similarity	NPD9500	Approved
0.6831	Remote Similarity	NPD4256	Phase 2
0.6831	Remote Similarity	NPD4257	Approved
0.6828	Remote Similarity	NPD7390	Discontinued
0.6824	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1548	Phase 1
0.6818	Remote Similarity	NPD2231	Phase 2
0.6818	Remote Similarity	NPD2561	Approved
0.6818	Remote Similarity	NPD3070	Discontinued
0.6818	Remote Similarity	NPD2235	Phase 2
0.6818	Remote Similarity	NPD2562	Approved
0.6812	Remote Similarity	NPD2979	Phase 3
0.6812	Remote Similarity	NPD1613	Approved
0.6812	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6099	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