NPASS Compound

Structure

CID176279 OpenBabel06191715552D 21 23 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 0.0000 -2.0000 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 -0.0000 1.0000 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 1.7321 0.0000 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 0.8660 -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 0.8660 -0.5000 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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 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 10 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 16 2 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.23
Volume:	329.688
LogP:	6.146
LogD:	4.737
LogS:	-6.047
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	3.389
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:	-5.015
MDCK Permeability:	1.1975819688814227e-05
Pgp-inhibitor:	0.798
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.223
Plasma Protein Binding (PPB):	98.25569152832031%
Volume Distribution (VD):	3.034
Pgp-substrate:	2.186680555343628%

ADMET: Metabolism

CYP1A2-inhibitor:	0.263
CYP1A2-substrate:	0.87
CYP2C19-inhibitor:	0.466
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.244
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.707
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.494
CYP3A4-substrate:	0.548

ADMET: Excretion

Clearance (CL):	9.002
Half-life (T1/2):	0.079

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.419
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.863
Carcinogencity:	0.1
Eye Corrosion:	0.063
Eye Irritation:	0.928
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: NPC176279

Natural Product ID:	NPC176279
*Common Name:**	Sempervirol
IUPAC Name:	(4bS,8aS)-4b,8,8-trimethyl-3-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol
Synonyms:	Sempervirol
Standard InCHIKey:	RSIJAQZNHHXEJZ-AZUAARDMSA-N
Standard InCHI:	InChI=1S/C20H30O/c1-13(2)15-12-16-14(11-17(15)21)7-8-18-19(3,4)9-6-10-20(16,18)5/h11-13,18,21H,6-10H2,1-5H3/t18-,20+/m0/s1
SMILES:	CC(c1cc2c(cc1O)CC[C@@H]1[C@]2(C)CCCC1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097038
PubChem CID:	12442761
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
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	feces	n.a.	n.a.	PMID[20402524]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8300	Apis mellifera ligustica	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO882	Trogopterus xanthipes	Species	Sciuridae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	40000.0	nM	PMID[466537]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[466537]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	40000.0	nM	PMID[466537]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	40000.0	nM	PMID[466537]

☑ 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 NPC176279 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	370
0.1-0.2	1875
0.2-0.3	4110
0.3-0.4	10746
0.4-0.5	8854
0.5-0.6	10344
0.6-0.7	5019
0.7-0.8	1087
0.8-0.85	177
0.85-0.9	69
0.9-0.95	32
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC260323
0.9717	High Similarity	NPC195922
0.9714	High Similarity	NPC250323
0.9712	High Similarity	NPC141782
0.9626	High Similarity	NPC192948
0.9626	High Similarity	NPC35797
0.9612	High Similarity	NPC151477
0.9537	High Similarity	NPC477137
0.9537	High Similarity	NPC471668
0.9537	High Similarity	NPC38893
0.9537	High Similarity	NPC308311
0.9524	High Similarity	NPC13482
0.945	High Similarity	NPC172219
0.945	High Similarity	NPC304510
0.9439	High Similarity	NPC715
0.9417	High Similarity	NPC117115
0.9364	High Similarity	NPC471671
0.9358	High Similarity	NPC219112
0.9352	High Similarity	NPC268160
0.9346	High Similarity	NPC46940
0.9327	High Similarity	NPC21594
0.9279	High Similarity	NPC93071
0.9279	High Similarity	NPC126002
0.9279	High Similarity	NPC469644
0.9273	High Similarity	NPC477136
0.9266	High Similarity	NPC147179
0.9252	High Similarity	NPC322753
0.9252	High Similarity	NPC95716
0.9245	High Similarity	NPC58865
0.9182	High Similarity	NPC308828
0.9182	High Similarity	NPC469663
0.9182	High Similarity	NPC92
0.9151	High Similarity	NPC11554
0.9099	High Similarity	NPC16030
0.9091	High Similarity	NPC469719
0.9074	High Similarity	NPC77772
0.9074	High Similarity	NPC151537
0.9065	High Similarity	NPC314187
0.9035	High Similarity	NPC249340
0.9035	High Similarity	NPC162935
0.9029	High Similarity	NPC211885
0.9018	High Similarity	NPC469609
0.9018	High Similarity	NPC154030
0.8981	High Similarity	NPC132720
0.8962	High Similarity	NPC271274
0.8957	High Similarity	NPC11250
0.8947	High Similarity	NPC32322
0.8947	High Similarity	NPC259703
0.8909	High Similarity	NPC317869
0.8909	High Similarity	NPC322239
0.8899	High Similarity	NPC266937
0.8899	High Similarity	NPC470770
0.8879	High Similarity	NPC471187
0.887	High Similarity	NPC154696
0.886	High Similarity	NPC135467
0.886	High Similarity	NPC260832
0.885	High Similarity	NPC206
0.8846	High Similarity	NPC225506
0.8839	High Similarity	NPC141001
0.8829	High Similarity	NPC471534
0.8818	High Similarity	NPC62867
0.8818	High Similarity	NPC471179
0.8818	High Similarity	NPC177962
0.8818	High Similarity	NPC228425
0.8803	High Similarity	NPC181334
0.8793	High Similarity	NPC176208
0.8783	High Similarity	NPC241001
0.8774	High Similarity	NPC238696
0.8762	High Similarity	NPC252105
0.8761	High Similarity	NPC299180
0.875	High Similarity	NPC252821
0.875	High Similarity	NPC122005
0.875	High Similarity	NPC299762
0.875	High Similarity	NPC33675
0.8729	High Similarity	NPC137750
0.8707	High Similarity	NPC253627
0.8704	High Similarity	NPC320439
0.8684	High Similarity	NPC164649
0.8684	High Similarity	NPC48342
0.8655	High Similarity	NPC325294
0.8655	High Similarity	NPC321822
0.8655	High Similarity	NPC100414
0.8655	High Similarity	NPC43000
0.8654	High Similarity	NPC77492
0.8654	High Similarity	NPC79241
0.8654	High Similarity	NPC6597
0.8641	High Similarity	NPC144682
0.8641	High Similarity	NPC222146
0.8636	High Similarity	NPC296683
0.8632	High Similarity	NPC121168
0.8632	High Similarity	NPC297057
0.8632	High Similarity	NPC471794
0.8621	High Similarity	NPC328504
0.8609	High Similarity	NPC151197
0.8609	High Similarity	NPC42657
0.8598	High Similarity	NPC272029
0.8585	High Similarity	NPC51015
0.8584	High Similarity	NPC246760
0.8584	High Similarity	NPC84999
0.8583	High Similarity	NPC176130
0.8583	High Similarity	NPC78364
0.8583	High Similarity	NPC108164
0.8583	High Similarity	NPC471077
0.8583	High Similarity	NPC69424
0.8583	High Similarity	NPC84672
0.8571	High Similarity	NPC321589
0.8571	High Similarity	NPC124030
0.8571	High Similarity	NPC263753
0.8559	High Similarity	NPC198014
0.8559	High Similarity	NPC469912
0.8558	High Similarity	NPC312132
0.8558	High Similarity	NPC259512
0.8534	High Similarity	NPC190501
0.8534	High Similarity	NPC478121
0.8534	High Similarity	NPC99734
0.8534	High Similarity	NPC318552
0.8519	High Similarity	NPC99557
0.8519	High Similarity	NPC47284
0.8519	High Similarity	NPC219286
0.8519	High Similarity	NPC243601
0.8519	High Similarity	NPC138942
0.8509	High Similarity	NPC247858
0.8509	High Similarity	NPC474358
0.8509	High Similarity	NPC257540
0.8509	High Similarity	NPC474387
0.8509	High Similarity	NPC137496
0.8509	High Similarity	NPC312105
0.8509	High Similarity	NPC154511
0.8505	High Similarity	NPC168829
0.8505	High Similarity	NPC269212
0.8496	Intermediate Similarity	NPC107240
0.8496	Intermediate Similarity	NPC249270
0.8491	Intermediate Similarity	NPC72729
0.8476	Intermediate Similarity	NPC225464
0.8475	Intermediate Similarity	NPC478058
0.8475	Intermediate Similarity	NPC71094
0.8475	Intermediate Similarity	NPC152946
0.8468	Intermediate Similarity	NPC224870
0.8462	Intermediate Similarity	NPC8392
0.8455	Intermediate Similarity	NPC64586
0.8448	Intermediate Similarity	NPC176893
0.8443	Intermediate Similarity	NPC276238
0.844	Intermediate Similarity	NPC53740
0.843	Intermediate Similarity	NPC72667
0.8426	Intermediate Similarity	NPC288411
0.8417	Intermediate Similarity	NPC76119
0.8417	Intermediate Similarity	NPC87985
0.8417	Intermediate Similarity	NPC4286
0.8407	Intermediate Similarity	NPC117846
0.8396	Intermediate Similarity	NPC92730
0.839	Intermediate Similarity	NPC142198
0.839	Intermediate Similarity	NPC77569
0.8376	Intermediate Similarity	NPC103916
0.8374	Intermediate Similarity	NPC108129
0.8365	Intermediate Similarity	NPC27323
0.8365	Intermediate Similarity	NPC245187
0.8365	Intermediate Similarity	NPC316301
0.8365	Intermediate Similarity	NPC152415
0.8365	Intermediate Similarity	NPC289769
0.8364	Intermediate Similarity	NPC27252
0.8364	Intermediate Similarity	NPC472979
0.8361	Intermediate Similarity	NPC201069
0.8348	Intermediate Similarity	NPC261973
0.8347	Intermediate Similarity	NPC254492
0.8333	Intermediate Similarity	NPC224342
0.8333	Intermediate Similarity	NPC199273
0.8319	Intermediate Similarity	NPC302371
0.8319	Intermediate Similarity	NPC321402
0.8306	Intermediate Similarity	NPC471851
0.8305	Intermediate Similarity	NPC129176
0.8302	Intermediate Similarity	NPC32674
0.8302	Intermediate Similarity	NPC156313
0.8293	Intermediate Similarity	NPC303910
0.8293	Intermediate Similarity	NPC171460
0.8291	Intermediate Similarity	NPC323074
0.8288	Intermediate Similarity	NPC64642
0.8288	Intermediate Similarity	NPC472982
0.8288	Intermediate Similarity	NPC149455
0.8279	Intermediate Similarity	NPC186889
0.8279	Intermediate Similarity	NPC476536
0.8276	Intermediate Similarity	NPC25648
0.8273	Intermediate Similarity	NPC155072
0.8273	Intermediate Similarity	NPC54765
0.8273	Intermediate Similarity	NPC310456
0.8269	Intermediate Similarity	NPC55903
0.8257	Intermediate Similarity	NPC475225
0.8241	Intermediate Similarity	NPC477685
0.824	Intermediate Similarity	NPC321086
0.8235	Intermediate Similarity	NPC474115
0.823	Intermediate Similarity	NPC476632
0.823	Intermediate Similarity	NPC165770
0.823	Intermediate Similarity	NPC4493
0.823	Intermediate Similarity	NPC470723
0.823	Intermediate Similarity	NPC224527
0.823	Intermediate Similarity	NPC225679
0.822	Intermediate Similarity	NPC318581
0.822	Intermediate Similarity	NPC325544
0.822	Intermediate Similarity	NPC68339
0.822	Intermediate Similarity	NPC477037
0.8214	Intermediate Similarity	NPC186385

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 NPC176279 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	997
0.2-0.3	1241
0.3-0.4	2977
0.4-0.5	1961
0.5-0.6	1178
0.6-0.7	325
0.7-0.8	88
0.8-0.85	14
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8879	High Similarity	NPD2342	Discontinued
0.8684	High Similarity	NPD3091	Approved
0.8649	High Similarity	NPD7635	Approved
0.8641	High Similarity	NPD1809	Phase 2
0.8558	High Similarity	NPD288	Approved
0.8534	High Similarity	NPD4059	Approved
0.8534	High Similarity	NPD3019	Approved
0.8462	Intermediate Similarity	NPD844	Approved
0.8396	Intermediate Similarity	NPD3020	Approved
0.839	Intermediate Similarity	NPD3092	Approved
0.8376	Intermediate Similarity	NPD2932	Approved
0.8365	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD845	Approved
0.822	Intermediate Similarity	NPD3095	Discontinued
0.8214	Intermediate Similarity	NPD4750	Phase 3
0.8148	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD4093	Discontinued
0.8115	Intermediate Similarity	NPD3094	Phase 2
0.8113	Intermediate Similarity	NPD2859	Approved
0.8113	Intermediate Similarity	NPD2860	Approved
0.8067	Intermediate Similarity	NPD1751	Approved
0.8067	Intermediate Similarity	NPD2286	Discontinued
0.8053	Intermediate Similarity	NPD3021	Approved
0.8053	Intermediate Similarity	NPD3022	Approved
0.8019	Intermediate Similarity	NPD2934	Approved
0.8019	Intermediate Similarity	NPD2933	Approved
0.7984	Intermediate Similarity	NPD5736	Approved
0.7969	Intermediate Similarity	NPD4097	Suspended
0.7951	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD2606	Approved
0.792	Intermediate Similarity	NPD2605	Approved
0.7857	Intermediate Similarity	NPD5156	Approved
0.7857	Intermediate Similarity	NPD5155	Approved
0.7851	Intermediate Similarity	NPD3026	Approved
0.7851	Intermediate Similarity	NPD3023	Approved
0.784	Intermediate Similarity	NPD3635	Approved
0.784	Intermediate Similarity	NPD3637	Approved
0.784	Intermediate Similarity	NPD3636	Approved
0.7833	Intermediate Similarity	NPD3025	Approved
0.7833	Intermediate Similarity	NPD3024	Approved
0.7778	Intermediate Similarity	NPD3595	Approved
0.7778	Intermediate Similarity	NPD3594	Approved
0.7769	Intermediate Similarity	NPD4589	Approved
0.7769	Intermediate Similarity	NPD4626	Approved
0.776	Intermediate Similarity	NPD4624	Approved
0.776	Intermediate Similarity	NPD2195	Approved
0.776	Intermediate Similarity	NPD2194	Approved
0.7759	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD1792	Phase 2
0.7734	Intermediate Similarity	NPD6663	Approved
0.7731	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3620	Phase 2
0.7674	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD5304	Approved
0.7603	Intermediate Similarity	NPD5303	Approved
0.76	Intermediate Similarity	NPD6696	Suspended
0.7589	Intermediate Similarity	NPD846	Approved
0.7589	Intermediate Similarity	NPD940	Approved
0.7578	Intermediate Similarity	NPD4625	Phase 3
0.7563	Intermediate Similarity	NPD497	Approved
0.7522	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD5327	Phase 3
0.75	Intermediate Similarity	NPD111	Approved
0.75	Intermediate Similarity	NPD1201	Approved
0.748	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD2229	Approved
0.7479	Intermediate Similarity	NPD495	Approved
0.7479	Intermediate Similarity	NPD2234	Approved
0.7479	Intermediate Similarity	NPD498	Approved
0.7479	Intermediate Similarity	NPD2228	Approved
0.7479	Intermediate Similarity	NPD496	Approved
0.7478	Intermediate Similarity	NPD1444	Approved
0.7478	Intermediate Similarity	NPD1445	Approved
0.7459	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7742	Approved
0.7444	Intermediate Similarity	NPD7743	Approved
0.7438	Intermediate Similarity	NPD7340	Approved
0.7405	Intermediate Similarity	NPD4140	Approved
0.7405	Intermediate Similarity	NPD4060	Phase 1
0.7402	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD5691	Approved
0.7385	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4749	Approved
0.736	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5735	Approved
0.7345	Intermediate Similarity	NPD1242	Phase 1
0.7333	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4725	Approved
0.7333	Intermediate Similarity	NPD4721	Approved
0.7333	Intermediate Similarity	NPD1398	Phase 1
0.7333	Intermediate Similarity	NPD4726	Approved
0.7323	Intermediate Similarity	NPD1283	Approved
0.7317	Intermediate Similarity	NPD7330	Discontinued
0.7313	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7003	Approved
0.7293	Intermediate Similarity	NPD6353	Approved
0.7266	Intermediate Similarity	NPD1470	Approved
0.7259	Intermediate Similarity	NPD5404	Approved
0.7259	Intermediate Similarity	NPD5406	Approved
0.7259	Intermediate Similarity	NPD5405	Approved
0.7259	Intermediate Similarity	NPD5408	Approved
0.7258	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD1651	Approved
0.7252	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3638	Discontinued
0.7217	Intermediate Similarity	NPD9500	Approved
0.7213	Intermediate Similarity	NPD6671	Approved
0.7185	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2861	Phase 2
0.7143	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD3143	Discontinued
0.7132	Intermediate Similarity	NPD6099	Approved
0.7132	Intermediate Similarity	NPD6100	Approved
0.7131	Intermediate Similarity	NPD1791	Approved
0.7131	Intermediate Similarity	NPD5951	Approved
0.7131	Intermediate Similarity	NPD1793	Approved
0.7122	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4908	Phase 1
0.7092	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1281	Approved
0.7068	Intermediate Similarity	NPD8032	Phase 2
0.705	Intermediate Similarity	NPD8166	Discontinued
0.7049	Intermediate Similarity	NPD5283	Phase 1
0.7043	Intermediate Similarity	NPD3028	Approved
0.7031	Intermediate Similarity	NPD2230	Approved
0.7031	Intermediate Similarity	NPD3070	Discontinued
0.7031	Intermediate Similarity	NPD2233	Approved
0.7031	Intermediate Similarity	NPD2232	Approved
0.7021	Intermediate Similarity	NPD7041	Phase 2
0.7021	Intermediate Similarity	NPD2420	Approved
0.7021	Intermediate Similarity	NPD2421	Approved
0.7021	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7636	Approved
0.7015	Intermediate Similarity	NPD3109	Approved
0.7015	Intermediate Similarity	NPD3110	Approved
0.6992	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2209	Approved
0.6978	Remote Similarity	NPD2211	Approved
0.6977	Remote Similarity	NPD1669	Approved
0.6972	Remote Similarity	NPD3645	Discontinued
0.6972	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3657	Discovery
0.6953	Remote Similarity	NPD1611	Approved
0.6953	Remote Similarity	NPD1610	Phase 2
0.6947	Remote Similarity	NPD6584	Phase 3
0.6935	Remote Similarity	NPD709	Approved
0.6929	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7095	Approved
0.6912	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7037	Approved
0.6906	Remote Similarity	NPD4257	Approved
0.6906	Remote Similarity	NPD4256	Phase 2
0.6894	Remote Similarity	NPD4208	Discontinued
0.6885	Remote Similarity	NPD228	Approved
0.688	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1980	Approved
0.6875	Remote Similarity	NPD1981	Approved
0.6875	Remote Similarity	NPD1983	Approved
0.6866	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD9608	Approved
0.6864	Remote Similarity	NPD9610	Approved
0.686	Remote Similarity	NPD5451	Approved
0.6857	Remote Similarity	NPD6674	Discontinued
0.6855	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7157	Approved
0.6797	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2668	Approved
0.6797	Remote Similarity	NPD2667	Approved
0.6794	Remote Similarity	NPD8651	Approved
0.6788	Remote Similarity	NPD2157	Approved
0.6772	Remote Similarity	NPD7741	Discontinued
0.6767	Remote Similarity	NPD4212	Discontinued
0.6765	Remote Similarity	NPD6346	Approved
0.6765	Remote Similarity	NPD2979	Phase 3
0.6761	Remote Similarity	NPD8131	Suspended
0.6742	Remote Similarity	NPD1164	Approved
0.6741	Remote Similarity	NPD7294	Phase 1
0.6718	Remote Similarity	NPD4659	Approved
0.6718	Remote Similarity	NPD1755	Approved
0.6718	Remote Similarity	NPD6582	Phase 2
0.6718	Remote Similarity	NPD6583	Phase 3
0.6716	Remote Similarity	NPD4207	Discontinued
0.6714	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD9377	Approved
0.6694	Remote Similarity	NPD5535	Approved
0.6694	Remote Similarity	NPD9379	Approved
0.6693	Remote Similarity	NPD7644	Approved
0.6691	Remote Similarity	NPD4108	Discontinued
0.669	Remote Similarity	NPD6090	Discontinued
0.669	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD6387	Discontinued
0.6667	Remote Similarity	NPD4198	Discontinued

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