NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	546.21
Volume:	519.942
LogP:	2.623
LogD:	0.896
LogS:	-3.8
# Rotatable Bonds:	7
TPSA:	175.37
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.289
Synthetic Accessibility Score:	4.953
Fsp3:	0.72
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.156
MDCK Permeability:	3.948392259189859e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.253
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.753

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	95.84933471679688%
Volume Distribution (VD):	1.288
Pgp-substrate:	1.8792020082473755%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.284
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.273
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.023

ADMET: Excretion

Clearance (CL):	1.341
Half-life (T1/2):	0.181

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.881
AMES Toxicity:	0.411
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.282
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.041
Respiratory Toxicity:	0.2

Download Data

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

Natural Product: NPC478044

Natural Product ID:	NPC478044
*Common Name:**	Suncheonoside D
IUPAC Name:	S-methyl 3,5-dimethyl-2-propan-2-yl-4,6-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]benzenecarbothioate
Synonyms:
Standard InCHIKey:	JEZSIZIVEGJGBG-FGUYRURZSA-N
Standard InCHI:	InChI=1S/C25H38O11S/c1-8(2)13-9(3)21(35-24-19(30)17(28)15(26)11(5)33-24)10(4)22(14(13)23(32)37-7)36-25-20(31)18(29)16(27)12(6)34-25/h8,11-12,15-20,24-31H,1-7H3/t11-,12-,15-,16-,17+,18+,19+,20+,24-,25-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(C(=C(C(=C2C)C(C)C)C(=O)SC)O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O)O)O)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122180312
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO33687	Streptomyces sp. SSC21	Species	Streptomycetaceae	Bacteria	isolated from a sediment sample	Suncheon Bay, Korea	2013	PMID[26078114]

☑ 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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	75	%	PMID[26078114]

☑ 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 NPC478044 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	403
0.1-0.2	1797
0.2-0.3	3663
0.3-0.4	8878
0.4-0.5	9996
0.5-0.6	5948
0.6-0.7	7244
0.7-0.8	4618
0.8-0.85	135
0.85-0.9	12
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.974	High Similarity	NPC478042
0.9615	High Similarity	NPC478041
0.8683	High Similarity	NPC473202
0.8675	High Similarity	NPC178851
0.8639	High Similarity	NPC213052
0.8631	High Similarity	NPC477670
0.8598	High Similarity	NPC470358
0.8588	High Similarity	NPC63105
0.8571	High Similarity	NPC259905
0.8538	High Similarity	NPC46958
0.8521	High Similarity	NPC298778
0.848	Intermediate Similarity	NPC474345
0.8471	Intermediate Similarity	NPC30432
0.8471	Intermediate Similarity	NPC111536
0.8471	Intermediate Similarity	NPC271385
0.8471	Intermediate Similarity	NPC5029
0.8471	Intermediate Similarity	NPC76128
0.8466	Intermediate Similarity	NPC477687
0.8466	Intermediate Similarity	NPC477671
0.8447	Intermediate Similarity	NPC38775
0.8439	Intermediate Similarity	NPC84494
0.8439	Intermediate Similarity	NPC245059
0.843	Intermediate Similarity	NPC475246
0.8402	Intermediate Similarity	NPC249977
0.8393	Intermediate Similarity	NPC7752
0.8391	Intermediate Similarity	NPC470453
0.8391	Intermediate Similarity	NPC477860
0.8391	Intermediate Similarity	NPC470448
0.8391	Intermediate Similarity	NPC470452
0.8391	Intermediate Similarity	NPC164047
0.8391	Intermediate Similarity	NPC475161
0.8383	Intermediate Similarity	NPC216752
0.8372	Intermediate Similarity	NPC199533
0.8372	Intermediate Similarity	NPC68381
0.8372	Intermediate Similarity	NPC146803
0.8372	Intermediate Similarity	NPC3718
0.8372	Intermediate Similarity	NPC470454
0.8354	Intermediate Similarity	NPC470603
0.8354	Intermediate Similarity	NPC470605
0.8354	Intermediate Similarity	NPC470604
0.8352	Intermediate Similarity	NPC475352
0.8352	Intermediate Similarity	NPC229817
0.8352	Intermediate Similarity	NPC475220
0.8352	Intermediate Similarity	NPC473686
0.8352	Intermediate Similarity	NPC221140
0.8343	Intermediate Similarity	NPC475662
0.8343	Intermediate Similarity	NPC473631
0.8343	Intermediate Similarity	NPC473717
0.8343	Intermediate Similarity	NPC293227
0.8324	Intermediate Similarity	NPC475233
0.8323	Intermediate Similarity	NPC472345
0.8314	Intermediate Similarity	NPC98776
0.8313	Intermediate Similarity	NPC279732
0.8303	Intermediate Similarity	NPC477675
0.8303	Intermediate Similarity	NPC477674
0.8303	Intermediate Similarity	NPC17521
0.8293	Intermediate Similarity	NPC78021
0.8293	Intermediate Similarity	NPC268950
0.8293	Intermediate Similarity	NPC211158
0.8293	Intermediate Similarity	NPC108706
0.8293	Intermediate Similarity	NPC87304
0.8284	Intermediate Similarity	NPC475979
0.8282	Intermediate Similarity	NPC250488
0.8282	Intermediate Similarity	NPC477672
0.8282	Intermediate Similarity	NPC477673
0.8282	Intermediate Similarity	NPC190217
0.8253	Intermediate Similarity	NPC470606
0.8249	Intermediate Similarity	NPC87583
0.8246	Intermediate Similarity	NPC222455
0.8246	Intermediate Similarity	NPC191653
0.8229	Intermediate Similarity	NPC212290
0.8229	Intermediate Similarity	NPC299149
0.8229	Intermediate Similarity	NPC114257
0.8229	Intermediate Similarity	NPC277710
0.8229	Intermediate Similarity	NPC153578
0.8225	Intermediate Similarity	NPC124155
0.8225	Intermediate Similarity	NPC257566
0.8225	Intermediate Similarity	NPC17432
0.8221	Intermediate Similarity	NPC106025
0.8221	Intermediate Similarity	NPC477240
0.8221	Intermediate Similarity	NPC213723
0.8221	Intermediate Similarity	NPC214454
0.821	Intermediate Similarity	NPC470359
0.8204	Intermediate Similarity	NPC470607
0.8204	Intermediate Similarity	NPC308265
0.8187	Intermediate Similarity	NPC112749
0.8187	Intermediate Similarity	NPC477502
0.8182	Intermediate Similarity	NPC477669
0.8176	Intermediate Similarity	NPC294722
0.8176	Intermediate Similarity	NPC99216
0.8171	Intermediate Similarity	NPC134819
0.8166	Intermediate Similarity	NPC44947
0.8166	Intermediate Similarity	NPC190450
0.8166	Intermediate Similarity	NPC259834
0.8155	Intermediate Similarity	NPC472320
0.8155	Intermediate Similarity	NPC271479
0.8155	Intermediate Similarity	NPC328093
0.815	Intermediate Similarity	NPC471688
0.8144	Intermediate Similarity	NPC23817
0.814	Intermediate Similarity	NPC470206
0.814	Intermediate Similarity	NPC470207
0.8129	Intermediate Similarity	NPC472621
0.8129	Intermediate Similarity	NPC70441
0.8122	Intermediate Similarity	NPC470199
0.8122	Intermediate Similarity	NPC314459
0.811	Intermediate Similarity	NPC191154
0.8107	Intermediate Similarity	NPC47923
0.8103	Intermediate Similarity	NPC208668
0.8103	Intermediate Similarity	NPC25724
0.8103	Intermediate Similarity	NPC472054
0.8098	Intermediate Similarity	NPC199335
0.8092	Intermediate Similarity	NPC477571
0.8092	Intermediate Similarity	NPC78734
0.8092	Intermediate Similarity	NPC241874
0.8092	Intermediate Similarity	NPC150767
0.8092	Intermediate Similarity	NPC477573
0.8092	Intermediate Similarity	NPC477572
0.8084	Intermediate Similarity	NPC295613
0.8084	Intermediate Similarity	NPC261866
0.8084	Intermediate Similarity	NPC473657
0.8084	Intermediate Similarity	NPC206378
0.8084	Intermediate Similarity	NPC45165
0.8081	Intermediate Similarity	NPC472622
0.8081	Intermediate Similarity	NPC474024
0.8075	Intermediate Similarity	NPC18886
0.8072	Intermediate Similarity	NPC106625
0.8072	Intermediate Similarity	NPC472799
0.807	Intermediate Similarity	NPC284277
0.807	Intermediate Similarity	NPC15358
0.807	Intermediate Similarity	NPC475497
0.807	Intermediate Similarity	NPC475366
0.8066	Intermediate Similarity	NPC321046
0.8059	Intermediate Similarity	NPC474763
0.8059	Intermediate Similarity	NPC131745
0.8059	Intermediate Similarity	NPC300537
0.8059	Intermediate Similarity	NPC127782
0.8057	Intermediate Similarity	NPC469601
0.8057	Intermediate Similarity	NPC294149
0.8049	Intermediate Similarity	NPC307052
0.8049	Intermediate Similarity	NPC139966
0.8047	Intermediate Similarity	NPC473623
0.8047	Intermediate Similarity	NPC271270
0.8047	Intermediate Similarity	NPC97285
0.8047	Intermediate Similarity	NPC142860
0.8047	Intermediate Similarity	NPC246469
0.8047	Intermediate Similarity	NPC110349
0.8046	Intermediate Similarity	NPC256760
0.8045	Intermediate Similarity	NPC241847
0.8037	Intermediate Similarity	NPC23084
0.8037	Intermediate Similarity	NPC218685
0.8036	Intermediate Similarity	NPC257309
0.8035	Intermediate Similarity	NPC61791
0.8035	Intermediate Similarity	NPC293629
0.8035	Intermediate Similarity	NPC43587
0.8035	Intermediate Similarity	NPC5319
0.8034	Intermediate Similarity	NPC473883
0.8034	Intermediate Similarity	NPC313452
0.8033	Intermediate Similarity	NPC470195
0.8033	Intermediate Similarity	NPC470200
0.8033	Intermediate Similarity	NPC470193
0.8033	Intermediate Similarity	NPC470194
0.8033	Intermediate Similarity	NPC316274
0.8033	Intermediate Similarity	NPC470196
0.8033	Intermediate Similarity	NPC470197
0.8033	Intermediate Similarity	NPC282474
0.8033	Intermediate Similarity	NPC470198
0.8024	Intermediate Similarity	NPC169248
0.8024	Intermediate Similarity	NPC26195
0.8024	Intermediate Similarity	NPC97052
0.8024	Intermediate Similarity	NPC72649
0.8024	Intermediate Similarity	NPC39351
0.8024	Intermediate Similarity	NPC99233
0.8023	Intermediate Similarity	NPC329119
0.8023	Intermediate Similarity	NPC236934
0.8023	Intermediate Similarity	NPC5778
0.8012	Intermediate Similarity	NPC278419
0.8012	Intermediate Similarity	NPC473509
0.8012	Intermediate Similarity	NPC183672
0.8012	Intermediate Similarity	NPC475131
0.8012	Intermediate Similarity	NPC29830
0.8012	Intermediate Similarity	NPC259182
0.8012	Intermediate Similarity	NPC179198
0.8012	Intermediate Similarity	NPC121001
0.8012	Intermediate Similarity	NPC473770
0.8012	Intermediate Similarity	NPC66087
0.8012	Intermediate Similarity	NPC87708
0.8011	Intermediate Similarity	NPC255799
0.8011	Intermediate Similarity	NPC312630
0.8011	Intermediate Similarity	NPC324220
0.8	Intermediate Similarity	NPC199357
0.8	Intermediate Similarity	NPC105591
0.8	Intermediate Similarity	NPC474239
0.8	Intermediate Similarity	NPC65746
0.8	Intermediate Similarity	NPC203751
0.8	Intermediate Similarity	NPC182045
0.8	Intermediate Similarity	NPC303913
0.8	Intermediate Similarity	NPC85368
0.8	Intermediate Similarity	NPC474779
0.8	Intermediate Similarity	NPC477676
0.8	Intermediate Similarity	NPC469818

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 NPC478044 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	1047
0.2-0.3	2171
0.3-0.4	2739
0.4-0.5	1818
0.5-0.6	716
0.6-0.7	222
0.7-0.8	92
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8035	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7074	Phase 3
0.7931	Intermediate Similarity	NPD7054	Approved
0.7929	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6559	Discontinued
0.7895	Intermediate Similarity	NPD6959	Discontinued
0.7886	Intermediate Similarity	NPD7472	Approved
0.7857	Intermediate Similarity	NPD7819	Suspended
0.7805	Intermediate Similarity	NPD2533	Approved
0.7805	Intermediate Similarity	NPD2532	Approved
0.7805	Intermediate Similarity	NPD2534	Approved
0.7797	Intermediate Similarity	NPD7251	Discontinued
0.7753	Intermediate Similarity	NPD7808	Phase 3
0.774	Intermediate Similarity	NPD6797	Phase 2
0.7709	Intermediate Similarity	NPD8313	Approved
0.7709	Intermediate Similarity	NPD8312	Approved
0.767	Intermediate Similarity	NPD3818	Discontinued
0.7647	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7075	Discontinued
0.7609	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4380	Phase 2
0.7528	Intermediate Similarity	NPD5844	Phase 1
0.7514	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6674	Discontinued
0.7485	Intermediate Similarity	NPD1934	Approved
0.7485	Intermediate Similarity	NPD6801	Discontinued
0.7459	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6166	Phase 2
0.7458	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6651	Approved
0.7443	Intermediate Similarity	NPD7229	Phase 3
0.7443	Intermediate Similarity	NPD6232	Discontinued
0.7429	Intermediate Similarity	NPD5494	Approved
0.7394	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD8151	Discontinued
0.7374	Intermediate Similarity	NPD7228	Approved
0.7345	Intermediate Similarity	NPD5710	Approved
0.7345	Intermediate Similarity	NPD5711	Approved
0.7333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7783	Phase 2
0.731	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3817	Phase 2
0.7289	Intermediate Similarity	NPD2800	Approved
0.7288	Intermediate Similarity	NPD7199	Phase 2
0.7283	Intermediate Similarity	NPD37	Approved
0.7278	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6599	Discontinued
0.7257	Intermediate Similarity	NPD4966	Approved
0.7257	Intermediate Similarity	NPD4967	Phase 2
0.7257	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4965	Approved
0.7241	Intermediate Similarity	NPD8455	Phase 2
0.724	Intermediate Similarity	NPD6781	Approved
0.724	Intermediate Similarity	NPD6777	Approved
0.724	Intermediate Similarity	NPD6782	Approved
0.724	Intermediate Similarity	NPD6776	Approved
0.724	Intermediate Similarity	NPD6778	Approved
0.724	Intermediate Similarity	NPD6779	Approved
0.724	Intermediate Similarity	NPD6780	Approved
0.7238	Intermediate Similarity	NPD7286	Phase 2
0.7225	Intermediate Similarity	NPD7411	Suspended
0.7216	Intermediate Similarity	NPD7698	Approved
0.7216	Intermediate Similarity	NPD7696	Phase 3
0.7216	Intermediate Similarity	NPD7435	Discontinued
0.7216	Intermediate Similarity	NPD7697	Approved
0.7213	Intermediate Similarity	NPD7240	Approved
0.7205	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1652	Phase 2
0.7175	Intermediate Similarity	NPD6234	Discontinued
0.7173	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD6841	Approved
0.7166	Intermediate Similarity	NPD6843	Phase 3
0.7166	Intermediate Similarity	NPD6842	Approved
0.7158	Intermediate Similarity	NPD5953	Discontinued
0.7157	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD2801	Approved
0.7135	Intermediate Similarity	NPD7699	Phase 2
0.7135	Intermediate Similarity	NPD7700	Phase 2
0.7128	Intermediate Similarity	NPD7680	Approved
0.7126	Intermediate Similarity	NPD1549	Phase 2
0.7118	Intermediate Similarity	NPD6799	Approved
0.7111	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2796	Approved
0.7092	Intermediate Similarity	NPD7870	Phase 2
0.7092	Intermediate Similarity	NPD7871	Phase 2
0.7077	Intermediate Similarity	NPD6823	Phase 2
0.7076	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6535	Approved
0.7068	Intermediate Similarity	NPD6534	Approved
0.7066	Intermediate Similarity	NPD2346	Discontinued
0.7056	Intermediate Similarity	NPD3787	Discontinued
0.705	Intermediate Similarity	NPD7801	Approved
0.7041	Intermediate Similarity	NPD4628	Phase 3
0.7041	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1511	Approved
0.7011	Intermediate Similarity	NPD3226	Approved
0.7006	Intermediate Similarity	NPD5402	Approved
0.7006	Intermediate Similarity	NPD6100	Approved
0.7006	Intermediate Similarity	NPD6099	Approved
0.7005	Intermediate Similarity	NPD8319	Approved
0.7005	Intermediate Similarity	NPD8320	Phase 1
0.7	Intermediate Similarity	NPD7874	Approved
0.7	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3751	Discontinued
0.6994	Remote Similarity	NPD7985	Registered
0.6978	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3882	Suspended
0.6966	Remote Similarity	NPD7768	Phase 2
0.6941	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1512	Approved
0.6935	Remote Similarity	NPD7584	Approved
0.6914	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7458	Discontinued
0.6897	Remote Similarity	NPD5403	Approved
0.6879	Remote Similarity	NPD5401	Approved
0.6867	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5124	Phase 1
0.6857	Remote Similarity	NPD1653	Approved
0.6845	Remote Similarity	NPD1510	Phase 2
0.6842	Remote Similarity	NPD8150	Discontinued
0.6839	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6212	Phase 3
0.6839	Remote Similarity	NPD6213	Phase 3
0.6826	Remote Similarity	NPD1607	Approved
0.6821	Remote Similarity	NPD7390	Discontinued
0.68	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.68	Remote Similarity	NPD920	Approved
0.6796	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7930	Approved
0.6755	Remote Similarity	NPD7685	Pre-registration
0.6754	Remote Similarity	NPD8434	Phase 2
0.6746	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8366	Approved
0.6744	Remote Similarity	NPD3750	Approved
0.6744	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.674	Remote Similarity	NPD3749	Approved
0.6707	Remote Similarity	NPD1240	Approved
0.6706	Remote Similarity	NPD2935	Discontinued
0.6706	Remote Similarity	NPD1551	Phase 2
0.6703	Remote Similarity	NPD919	Approved
0.6687	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1243	Approved
0.6683	Remote Similarity	NPD7583	Approved
0.6667	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6765	Approved
0.665	Remote Similarity	NPD7585	Approved
0.6648	Remote Similarity	NPD5049	Phase 3
0.6647	Remote Similarity	NPD3748	Approved
0.6647	Remote Similarity	NPD2799	Discontinued
0.6634	Remote Similarity	NPD7999	Approved
0.6633	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.663	Remote Similarity	NPD1247	Approved
0.662	Remote Similarity	NPD8491	Approved
0.6608	Remote Similarity	NPD2531	Phase 2
0.6591	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD8469	Approved
0.6571	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3926	Phase 2
0.6557	Remote Similarity	NPD6971	Discontinued
0.6556	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD6273	Approved
0.6548	Remote Similarity	NPD4363	Phase 3
0.6548	Remote Similarity	NPD4360	Phase 2
0.6543	Remote Similarity	NPD1091	Approved
0.6541	Remote Similarity	NPD8127	Discontinued
0.6534	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD4625	Phase 3
0.6512	Remote Similarity	NPD8059	Phase 3
0.6512	Remote Similarity	NPD2438	Suspended
0.6512	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD1613	Approved
0.65	Remote Similarity	NPD8285	Discontinued
0.6488	Remote Similarity	NPD2313	Discontinued
0.6488	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5760	Phase 2
0.6484	Remote Similarity	NPD5761	Phase 2
0.6478	Remote Similarity	NPD7340	Approved
0.6474	Remote Similarity	NPD5763	Approved
0.6474	Remote Similarity	NPD7266	Discontinued
0.6474	Remote Similarity	NPD5762	Approved
0.6471	Remote Similarity	NPD6355	Discontinued
0.6471	Remote Similarity	NPD1933	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