NPASS Compound

Structure

NPC259703 OpenBabel07101718282D 22 24 0 0 1 0 0 0 0 0999 V2000 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -1.7321 -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 0.0000 -2.0000 0.0000 C 0 0 0 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 -1.7321 -3.0000 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 -2.5981 -1.5000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 0.8660 -0.5000 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 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 7 2 0 0 0 0 6 13 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.19
Volume:	333.205
LogP:	4.492
LogD:	4.043
LogS:	-4.142
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.808
Synthetic Accessibility Score:	3.882
Fsp3:	0.55
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:	-5.094
MDCK Permeability:	2.272952042403631e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.471
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	96.9549560546875%
Volume Distribution (VD):	1.234
Pgp-substrate:	4.339424133300781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.819
CYP1A2-substrate:	0.881
CYP2C19-inhibitor:	0.545
CYP2C19-substrate:	0.904
CYP2C9-inhibitor:	0.496
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.441
CYP2D6-substrate:	0.856
CYP3A4-inhibitor:	0.501
CYP3A4-substrate:	0.681

ADMET: Excretion

Clearance (CL):	13.081
Half-life (T1/2):	0.382

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.421
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.239
Carcinogencity:	0.349
Eye Corrosion:	0.004
Eye Irritation:	0.534
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC259703

Natural Product ID:	NPC259703
*Common Name:**	Hypargenin D
IUPAC Name:	(4aS,10aR)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-4,10a-dihydro-3H-phenanthren-2-one
Synonyms:	hypargenin D
Standard InCHIKey:	CRJHOCWYQXGNFV-FXAWDEMLSA-N
Standard InCHI:	InChI=1S/C20H26O2/c1-12(2)14-10-13-6-7-17-19(3,4)18(22)8-9-20(17,5)15(13)11-16(14)21/h6-7,10-12,17,21H,8-9H2,1-5H3/t17-,20+/m0/s1
SMILES:	CC(C)c1cc2C=C[C@H]3C(C)(C)C(=O)CC[C@]3(C)c2cc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487019
PubChem CID:	44559795
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
NPO26904	Salvia hypargeia	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[3236010]
NPO26904	Salvia hypargeia	Species	Lamiaceae	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	1
Others	5

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	62.5	ug.mL-1	PMID[491881]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	>	7.0	mm	PMID[491881]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IZ	>	7.0	mm	PMID[491881]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	>	7.0	mm	PMID[491881]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	>	7.0	mm	PMID[491881]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	>	7.0	mm	PMID[491881]

☑ 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 NPC259703 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	269
0.1-0.2	1492
0.2-0.3	2761
0.3-0.4	8101
0.4-0.5	10585
0.5-0.6	8468
0.6-0.7	8816
0.7-0.8	1903
0.8-0.85	188
0.85-0.9	80
0.9-0.95	28
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC32322
0.9739	High Similarity	NPC154696
0.9487	High Similarity	NPC176208
0.9483	High Similarity	NPC241001
0.9407	High Similarity	NPC471187
0.9402	High Similarity	NPC162935
0.9402	High Similarity	NPC249340
0.9328	High Similarity	NPC181334
0.9322	High Similarity	NPC121168
0.9322	High Similarity	NPC11250
0.9256	High Similarity	NPC72667
0.9244	High Similarity	NPC198014
0.9237	High Similarity	NPC253627
0.9231	High Similarity	NPC190501
0.9231	High Similarity	NPC318552
0.9204	High Similarity	NPC250323
0.9174	High Similarity	NPC71610
0.9174	High Similarity	NPC254492
0.9167	High Similarity	NPC199273
0.9145	High Similarity	NPC42657
0.9106	High Similarity	NPC171460
0.9106	High Similarity	NPC276238
0.9098	High Similarity	NPC69424
0.9098	High Similarity	NPC84672
0.9098	High Similarity	NPC176130
0.9098	High Similarity	NPC78364
0.9091	High Similarity	NPC137750
0.9091	High Similarity	NPC87985
0.9068	High Similarity	NPC478121
0.9027	High Similarity	NPC13482
0.9024	High Similarity	NPC96024
0.8983	High Similarity	NPC258366
0.8983	High Similarity	NPC31296
0.8983	High Similarity	NPC473974
0.8983	High Similarity	NPC79933
0.8974	High Similarity	NPC477136
0.8947	High Similarity	NPC176279
0.8947	High Similarity	NPC260323
0.8889	High Similarity	NPC165612
0.8889	High Similarity	NPC471668
0.888	High Similarity	NPC108129
0.8879	High Similarity	NPC195922
0.886	High Similarity	NPC141782
0.8852	High Similarity	NPC75432
0.8843	High Similarity	NPC282577
0.8833	High Similarity	NPC164852
0.881	High Similarity	NPC471851
0.8803	High Similarity	NPC192948
0.8803	High Similarity	NPC35797
0.88	High Similarity	NPC303910
0.877	High Similarity	NPC273683
0.8761	High Similarity	NPC228737
0.8761	High Similarity	NPC151477
0.8739	High Similarity	NPC328694
0.8729	High Similarity	NPC308311
0.8729	High Similarity	NPC477137
0.8729	High Similarity	NPC219112
0.8729	High Similarity	NPC38893
0.872	High Similarity	NPC3009
0.8718	High Similarity	NPC268160
0.8707	High Similarity	NPC46940
0.8707	High Similarity	NPC286222
0.8699	High Similarity	NPC15127
0.8673	High Similarity	NPC21594
0.8672	High Similarity	NPC78307
0.8672	High Similarity	NPC138472
0.8672	High Similarity	NPC477139
0.8667	High Similarity	NPC93071
0.8661	High Similarity	NPC476847
0.8655	High Similarity	NPC172219
0.8655	High Similarity	NPC304510
0.8651	High Similarity	NPC131684
0.8651	High Similarity	NPC206028
0.8644	High Similarity	NPC147179
0.864	High Similarity	NPC30491
0.864	High Similarity	NPC262936
0.8632	High Similarity	NPC715
0.8629	High Similarity	NPC123506
0.8621	High Similarity	NPC470770
0.8621	High Similarity	NPC95716
0.8621	High Similarity	NPC266937
0.8609	High Similarity	NPC58865
0.8605	High Similarity	NPC202225
0.8584	High Similarity	NPC117115
0.8583	High Similarity	NPC154030
0.8583	High Similarity	NPC471671
0.8571	High Similarity	NPC308828
0.8571	High Similarity	NPC469663
0.8571	High Similarity	NPC92
0.8547	High Similarity	NPC62867
0.8547	High Similarity	NPC177962
0.8538	High Similarity	NPC153088
0.8527	High Similarity	NPC49742
0.8527	High Similarity	NPC111845
0.8525	High Similarity	NPC21216
0.8522	High Similarity	NPC11554
0.8516	High Similarity	NPC291001
0.8516	High Similarity	NPC243305
0.8512	High Similarity	NPC126002
0.8512	High Similarity	NPC469644
0.8504	High Similarity	NPC117899
0.85	High Similarity	NPC16030
0.8492	Intermediate Similarity	NPC471530
0.8487	Intermediate Similarity	NPC469719
0.8468	Intermediate Similarity	NPC275145
0.8462	Intermediate Similarity	NPC77772
0.8462	Intermediate Similarity	NPC151537
0.8462	Intermediate Similarity	NPC322753
0.8438	Intermediate Similarity	NPC253488
0.843	Intermediate Similarity	NPC469609
0.8425	Intermediate Similarity	NPC48248
0.8425	Intermediate Similarity	NPC193203
0.8413	Intermediate Similarity	NPC269598
0.8409	Intermediate Similarity	NPC36868
0.8409	Intermediate Similarity	NPC475957
0.8409	Intermediate Similarity	NPC53001
0.84	Intermediate Similarity	NPC173978
0.84	Intermediate Similarity	NPC474766
0.8397	Intermediate Similarity	NPC283088
0.839	Intermediate Similarity	NPC228425
0.8387	Intermediate Similarity	NPC307174
0.8387	Intermediate Similarity	NPC478058
0.8385	Intermediate Similarity	NPC476282
0.8385	Intermediate Similarity	NPC53896
0.8376	Intermediate Similarity	NPC132720
0.8376	Intermediate Similarity	NPC296683
0.8372	Intermediate Similarity	NPC244699
0.8372	Intermediate Similarity	NPC474517
0.8372	Intermediate Similarity	NPC72669
0.8372	Intermediate Similarity	NPC18798
0.8359	Intermediate Similarity	NPC146647
0.8359	Intermediate Similarity	NPC34414
0.8346	Intermediate Similarity	NPC230811
0.8346	Intermediate Similarity	NPC87723
0.8333	Intermediate Similarity	NPC120693
0.8333	Intermediate Similarity	NPC8931
0.8333	Intermediate Similarity	NPC261573
0.8333	Intermediate Similarity	NPC471670
0.8321	Intermediate Similarity	NPC12070
0.8321	Intermediate Similarity	NPC293454
0.8321	Intermediate Similarity	NPC50924
0.8321	Intermediate Similarity	NPC27394
0.8308	Intermediate Similarity	NPC58685
0.8305	Intermediate Similarity	NPC471188
0.8295	Intermediate Similarity	NPC470725
0.8293	Intermediate Similarity	NPC260832
0.8293	Intermediate Similarity	NPC135467
0.8291	Intermediate Similarity	NPC314187
0.8281	Intermediate Similarity	NPC229894
0.8276	Intermediate Similarity	NPC320439
0.8271	Intermediate Similarity	NPC277559
0.8268	Intermediate Similarity	NPC3224
0.8264	Intermediate Similarity	NPC477453
0.8264	Intermediate Similarity	NPC141001
0.8258	Intermediate Similarity	NPC249272
0.8258	Intermediate Similarity	NPC103082
0.8254	Intermediate Similarity	NPC142956
0.8254	Intermediate Similarity	NPC164014
0.825	Intermediate Similarity	NPC471534
0.8244	Intermediate Similarity	NPC475627
0.8244	Intermediate Similarity	NPC475457
0.8244	Intermediate Similarity	NPC18982
0.8244	Intermediate Similarity	NPC475346
0.8244	Intermediate Similarity	NPC114183
0.8244	Intermediate Similarity	NPC115458
0.824	Intermediate Similarity	NPC164947
0.824	Intermediate Similarity	NPC152946
0.8235	Intermediate Similarity	NPC471179
0.8231	Intermediate Similarity	NPC239134
0.8231	Intermediate Similarity	NPC85342
0.823	Intermediate Similarity	NPC225506
0.823	Intermediate Similarity	NPC211885
0.8226	Intermediate Similarity	NPC474175
0.8226	Intermediate Similarity	NPC190971
0.822	Intermediate Similarity	NPC95126
0.822	Intermediate Similarity	NPC475002
0.8217	Intermediate Similarity	NPC25736
0.8217	Intermediate Similarity	NPC99731
0.8211	Intermediate Similarity	NPC151197
0.8211	Intermediate Similarity	NPC182240
0.8197	Intermediate Similarity	NPC299180
0.8195	Intermediate Similarity	NPC472308
0.819	Intermediate Similarity	NPC188677
0.819	Intermediate Similarity	NPC271274
0.8189	Intermediate Similarity	NPC4286
0.8189	Intermediate Similarity	NPC76119
0.8182	Intermediate Similarity	NPC213122
0.8182	Intermediate Similarity	NPC472262
0.8182	Intermediate Similarity	NPC270899
0.8182	Intermediate Similarity	NPC287604
0.8182	Intermediate Similarity	NPC161964
0.8175	Intermediate Similarity	NPC478164
0.8175	Intermediate Similarity	NPC135062
0.8174	Intermediate Similarity	NPC238696
0.8168	Intermediate Similarity	NPC312560
0.8167	Intermediate Similarity	NPC317869
0.8167	Intermediate Similarity	NPC322239
0.816	Intermediate Similarity	NPC120545
0.8158	Intermediate Similarity	NPC252105
0.8154	Intermediate Similarity	NPC55949

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 NPC259703 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	956
0.2-0.3	1085
0.3-0.4	2553
0.4-0.5	2305
0.5-0.6	1347
0.6-0.7	506
0.7-0.8	89
0.8-0.85	7
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9397	High Similarity	NPD2932	Approved
0.9231	High Similarity	NPD3019	Approved
0.8525	High Similarity	NPD3026	Approved
0.8525	High Similarity	NPD3023	Approved
0.8512	High Similarity	NPD3024	Approved
0.8512	High Similarity	NPD3025	Approved
0.8235	Intermediate Similarity	NPD7635	Approved
0.8231	Intermediate Similarity	NPD6663	Approved
0.8203	Intermediate Similarity	NPD5736	Approved
0.816	Intermediate Similarity	NPD1201	Approved
0.813	Intermediate Similarity	NPD3091	Approved
0.812	Intermediate Similarity	NPD2342	Discontinued
0.8065	Intermediate Similarity	NPD1651	Approved
0.8	Intermediate Similarity	NPD4059	Approved
0.7982	Intermediate Similarity	NPD3020	Approved
0.7969	Intermediate Similarity	NPD1283	Approved
0.7965	Intermediate Similarity	NPD288	Approved
0.7926	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD1470	Approved
0.7876	Intermediate Similarity	NPD1809	Phase 2
0.7876	Intermediate Similarity	NPD844	Approved
0.7874	Intermediate Similarity	NPD3092	Approved
0.7833	Intermediate Similarity	NPD4750	Phase 3
0.7823	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD8166	Discontinued
0.777	Intermediate Similarity	NPD7003	Approved
0.7759	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD6099	Approved
0.7737	Intermediate Similarity	NPD6100	Approved
0.7737	Intermediate Similarity	NPD5405	Approved
0.7737	Intermediate Similarity	NPD5406	Approved
0.7737	Intermediate Similarity	NPD5408	Approved
0.7737	Intermediate Similarity	NPD5404	Approved
0.7734	Intermediate Similarity	NPD1281	Approved
0.7719	Intermediate Similarity	NPD2859	Approved
0.7719	Intermediate Similarity	NPD2860	Approved
0.7717	Intermediate Similarity	NPD3095	Discontinued
0.7717	Intermediate Similarity	NPD4626	Approved
0.7699	Intermediate Similarity	NPD845	Approved
0.7687	Intermediate Similarity	NPD8032	Phase 2
0.7686	Intermediate Similarity	NPD3021	Approved
0.7686	Intermediate Similarity	NPD3022	Approved
0.7661	Intermediate Similarity	NPD5951	Approved
0.7634	Intermediate Similarity	NPD3094	Phase 2
0.7632	Intermediate Similarity	NPD2934	Approved
0.7632	Intermediate Similarity	NPD2933	Approved
0.7615	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7390	Discontinued
0.7589	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2286	Discontinued
0.7578	Intermediate Similarity	NPD1751	Approved
0.7518	Intermediate Similarity	NPD4097	Suspended
0.75	Intermediate Similarity	NPD4093	Discontinued
0.7481	Intermediate Similarity	NPD1755	Approved
0.7442	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3300	Phase 2
0.7402	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD3636	Approved
0.7388	Intermediate Similarity	NPD3637	Approved
0.7388	Intermediate Similarity	NPD3635	Approved
0.7372	Intermediate Similarity	NPD2979	Phase 3
0.7372	Intermediate Similarity	NPD4060	Phase 1
0.7368	Intermediate Similarity	NPD1164	Approved
0.7364	Intermediate Similarity	NPD5691	Approved
0.7333	Intermediate Similarity	NPD2606	Approved
0.7333	Intermediate Similarity	NPD2605	Approved
0.7313	Intermediate Similarity	NPD2194	Approved
0.7313	Intermediate Similarity	NPD2195	Approved
0.7313	Intermediate Similarity	NPD4624	Approved
0.7308	Intermediate Similarity	NPD4589	Approved
0.7308	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2346	Discontinued
0.728	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5156	Approved
0.7279	Intermediate Similarity	NPD4625	Phase 3
0.7279	Intermediate Similarity	NPD5155	Approved
0.7273	Intermediate Similarity	NPD3972	Approved
0.7258	Intermediate Similarity	NPD1792	Phase 2
0.725	Intermediate Similarity	NPD846	Approved
0.725	Intermediate Similarity	NPD940	Approved
0.7246	Intermediate Similarity	NPD4140	Approved
0.7244	Intermediate Similarity	NPD497	Approved
0.7239	Intermediate Similarity	NPD2797	Approved
0.7234	Intermediate Similarity	NPD2935	Discontinued
0.723	Intermediate Similarity	NPD7458	Discontinued
0.7206	Intermediate Similarity	NPD3594	Approved
0.7206	Intermediate Similarity	NPD3595	Approved
0.7185	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD2798	Approved
0.7177	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD496	Approved
0.7165	Intermediate Similarity	NPD2229	Approved
0.7165	Intermediate Similarity	NPD495	Approved
0.7165	Intermediate Similarity	NPD2234	Approved
0.7165	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2228	Approved
0.7165	Intermediate Similarity	NPD498	Approved
0.7164	Intermediate Similarity	NPD6696	Suspended
0.7163	Intermediate Similarity	NPD2799	Discontinued
0.7154	Intermediate Similarity	NPD5304	Approved
0.7154	Intermediate Similarity	NPD5303	Approved
0.7143	Intermediate Similarity	NPD6273	Approved
0.7122	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3620	Phase 2
0.7113	Intermediate Similarity	NPD2531	Phase 2
0.7113	Intermediate Similarity	NPD4477	Approved
0.7113	Intermediate Similarity	NPD4476	Approved
0.7113	Intermediate Similarity	NPD2438	Suspended
0.7109	Intermediate Similarity	NPD2629	Approved
0.7101	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3268	Approved
0.7101	Intermediate Similarity	NPD3764	Approved
0.709	Intermediate Similarity	NPD4749	Approved
0.709	Intermediate Similarity	NPD5327	Phase 3
0.7083	Intermediate Similarity	NPD2066	Phase 3
0.7068	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7028	Phase 2
0.7059	Intermediate Similarity	NPD3495	Discontinued
0.7054	Intermediate Similarity	NPD256	Approved
0.7054	Intermediate Similarity	NPD255	Approved
0.7049	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1778	Approved
0.7042	Intermediate Similarity	NPD7743	Approved
0.7042	Intermediate Similarity	NPD7742	Approved
0.7037	Intermediate Similarity	NPD1876	Approved
0.7034	Intermediate Similarity	NPD3750	Approved
0.7031	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7095	Approved
0.7025	Intermediate Similarity	NPD1242	Phase 1
0.7023	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD1444	Approved
0.7016	Intermediate Similarity	NPD1445	Approved
0.7015	Intermediate Similarity	NPD1608	Approved
0.7009	Intermediate Similarity	NPD1088	Approved
0.7007	Intermediate Similarity	NPD4208	Discontinued
0.7	Intermediate Similarity	NPD3226	Approved
0.7	Intermediate Similarity	NPD7340	Approved
0.7	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD943	Approved
0.6991	Remote Similarity	NPD111	Approved
0.6985	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.695	Remote Similarity	NPD5735	Approved
0.695	Remote Similarity	NPD6355	Discontinued
0.6947	Remote Similarity	NPD7610	Discontinued
0.6944	Remote Similarity	NPD4725	Approved
0.6944	Remote Similarity	NPD4726	Approved
0.6944	Remote Similarity	NPD4721	Approved
0.694	Remote Similarity	NPD1611	Approved
0.6929	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6671	Approved
0.6923	Remote Similarity	NPD3317	Approved
0.6918	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7473	Discontinued
0.6918	Remote Similarity	NPD4110	Phase 3
0.6911	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1930	Approved
0.6911	Remote Similarity	NPD1929	Approved
0.6906	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7008	Discontinued
0.6901	Remote Similarity	NPD6353	Approved
0.6901	Remote Similarity	NPD1607	Approved
0.6899	Remote Similarity	NPD1398	Phase 1
0.6894	Remote Similarity	NPD7330	Discontinued
0.6891	Remote Similarity	NPD1693	Approved
0.6891	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4878	Approved
0.6884	Remote Similarity	NPD2861	Phase 2
0.6857	Remote Similarity	NPD6798	Discontinued
0.6857	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3638	Discontinued
0.6849	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5585	Approved
0.6842	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1086	Approved
0.6838	Remote Similarity	NPD1090	Approved
0.6838	Remote Similarity	NPD1089	Approved
0.6835	Remote Similarity	NPD4207	Discontinued
0.6835	Remote Similarity	NPD6232	Discontinued
0.6828	Remote Similarity	NPD2344	Approved
0.6825	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7819	Suspended
0.6812	Remote Similarity	NPD257	Approved
0.6812	Remote Similarity	NPD258	Approved
0.6807	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4628	Phase 3
0.6803	Remote Similarity	NPD3400	Discontinued
0.6791	Remote Similarity	NPD17	Approved
0.679	Remote Similarity	NPD5190	Phase 2
0.6783	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD970	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data