NPASS Compound

Structure

NPC48860 OpenBabel07101718182D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.7146 4.7165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6745 2.1749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6924 4.1223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1999 3.4579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6290 3.4579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8597 1.7184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7651 1.7184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7146 3.7550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7651 2.6800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1942 2.6800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0269 1.2377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8597 2.6800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1942 1.7184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0269 3.1607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6290 0.9405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7146 0.6434 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1999 0.9405 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6796 2.9771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0269 0.2761 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0269 4.1223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1942 0.1626 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6924 3.1607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 3 22 1 0 0 0 0 4 8 2 0 0 0 0 4 9 1 0 0 0 0 5 8 1 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 9 18 1 1 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 21 2 0 0 0 0 16 17 1 6 0 0 0 16 23 1 0 0 0 0 17 2 1 6 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.13
Volume:	316.478
LogP:	2.056
LogD:	1.094
LogS:	-3.244
# Rotatable Bonds:	1
TPSA:	96.36
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.607
Synthetic Accessibility Score:	4.486
Fsp3:	0.529
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.718
MDCK Permeability:	1.23193040053593e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.241
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	90.90633392333984%
Volume Distribution (VD):	0.685
Pgp-substrate:	4.628167629241943%

ADMET: Metabolism

CYP1A2-inhibitor:	0.355
CYP1A2-substrate:	0.735
CYP2C19-inhibitor:	0.092
CYP2C19-substrate:	0.587
CYP2C9-inhibitor:	0.367
CYP2C9-substrate:	0.688
CYP2D6-inhibitor:	0.172
CYP2D6-substrate:	0.395
CYP3A4-inhibitor:	0.304
CYP3A4-substrate:	0.205

ADMET: Excretion

Clearance (CL):	11.558
Half-life (T1/2):	0.705

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.573
AMES Toxicity:	0.186
Rat Oral Acute Toxicity:	0.352
Maximum Recommended Daily Dose:	0.434
Skin Sensitization:	0.807
Carcinogencity:	0.039
Eye Corrosion:	0.012
Eye Irritation:	0.15
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: NPC48860

Natural Product ID:	NPC48860
*Common Name:**	UPIWWAMGNOLUMT-WKQJMJEJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UPIWWAMGNOLUMT-WKQJMJEJSA-N
Standard InCHI:	InChI=1S/C17H20O6/c1-8-4-9(18)7-17(2)16(23-17)15(21)13-10(5-8)14(20)12(22-3)6-11(13)19/h4,6,9,16,18-20H,5,7H2,1-3H3/b8-4-/t9-,16-,17-/m1/s1
SMILES:	COc1cc(O)c2c(c1O)C/C(=C[C@H](C[C@@]1([C@@H](C2=O)O1)C)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409097
PubChem CID:	71746988
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO33125	tricholoma terreum	Species	Tricholomataceae	Eukaryota	Fruiting Bodies	n.a.	n.a.	PMID[23837944]
NPO33125	tricholoma terreum	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28956915]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	21100.0	nM	PMID[550667]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	21000.0	nM	PMID[550667]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6500.0	nM	PMID[550667]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	14900.0	nM	PMID[550667]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	17800.0	nM	PMID[550667]

☑ 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 NPC48860 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	437
0.1-0.2	1751
0.2-0.3	4729
0.3-0.4	10387
0.4-0.5	7423
0.5-0.6	4365
0.6-0.7	5697
0.7-0.8	6344
0.8-0.85	1400
0.85-0.9	153
0.9-0.95	4
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC201560
0.9615	High Similarity	NPC191360
0.9057	High Similarity	NPC477410
0.9012	High Similarity	NPC472049
0.9	High Similarity	NPC161947
0.9	High Similarity	NPC155302
0.8987	High Similarity	NPC16082
0.8987	High Similarity	NPC82592
0.8987	High Similarity	NPC79998
0.8974	High Similarity	NPC103509
0.8957	High Similarity	NPC20237
0.8951	High Similarity	NPC475985
0.8944	High Similarity	NPC87431
0.8938	High Similarity	NPC476242
0.8938	High Similarity	NPC329091
0.8924	High Similarity	NPC281477
0.8902	High Similarity	NPC117854
0.8902	High Similarity	NPC158761
0.8902	High Similarity	NPC283041
0.8902	High Similarity	NPC477154
0.8902	High Similarity	NPC6588
0.8896	High Similarity	NPC224280
0.8896	High Similarity	NPC470457
0.8882	High Similarity	NPC263449
0.8875	High Similarity	NPC179732
0.8875	High Similarity	NPC241904
0.8875	High Similarity	NPC300727
0.8875	High Similarity	NPC84935
0.8875	High Similarity	NPC190020
0.8875	High Similarity	NPC77679
0.8868	High Similarity	NPC99381
0.8841	High Similarity	NPC477517
0.8841	High Similarity	NPC170245
0.8834	High Similarity	NPC470459
0.8834	High Similarity	NPC249181
0.8834	High Similarity	NPC41301
0.8834	High Similarity	NPC476822
0.8834	High Similarity	NPC7483
0.8827	High Similarity	NPC61010
0.8827	High Similarity	NPC308992
0.882	High Similarity	NPC152904
0.8812	High Similarity	NPC274730
0.8812	High Similarity	NPC150227
0.8812	High Similarity	NPC317383
0.8788	High Similarity	NPC470456
0.878	High Similarity	NPC234052
0.878	High Similarity	NPC475888
0.878	High Similarity	NPC191930
0.878	High Similarity	NPC326520
0.8773	High Similarity	NPC211107
0.8773	High Similarity	NPC472964
0.8773	High Similarity	NPC215612
0.8765	High Similarity	NPC200746
0.8765	High Similarity	NPC470183
0.8765	High Similarity	NPC14353
0.8765	High Similarity	NPC56085
0.8765	High Similarity	NPC472902
0.8765	High Similarity	NPC228785
0.8765	High Similarity	NPC246478
0.8758	High Similarity	NPC470402
0.8758	High Similarity	NPC469584
0.8758	High Similarity	NPC29841
0.8758	High Similarity	NPC474208
0.8758	High Similarity	NPC471479
0.8758	High Similarity	NPC235215
0.8758	High Similarity	NPC475267
0.8758	High Similarity	NPC7973
0.8758	High Similarity	NPC48208
0.8758	High Similarity	NPC156057
0.8758	High Similarity	NPC471515
0.8758	High Similarity	NPC472438
0.8758	High Similarity	NPC203891
0.8758	High Similarity	NPC78302
0.8758	High Similarity	NPC110070
0.8758	High Similarity	NPC162869
0.8758	High Similarity	NPC474836
0.8758	High Similarity	NPC101830
0.875	High Similarity	NPC199926
0.8742	High Similarity	NPC327225
0.8735	High Similarity	NPC247136
0.8734	High Similarity	NPC469619
0.8734	High Similarity	NPC469670
0.8734	High Similarity	NPC96501
0.8727	High Similarity	NPC470462
0.872	High Similarity	NPC474240
0.872	High Similarity	NPC248638
0.872	High Similarity	NPC152659
0.872	High Similarity	NPC236521
0.8718	High Similarity	NPC107625
0.8712	High Similarity	NPC173137
0.8712	High Similarity	NPC278052
0.8712	High Similarity	NPC40491
0.8712	High Similarity	NPC474186
0.8704	High Similarity	NPC4481
0.8704	High Similarity	NPC288669
0.8704	High Similarity	NPC18607
0.8704	High Similarity	NPC176300
0.8704	High Similarity	NPC22472
0.8704	High Similarity	NPC105242
0.8704	High Similarity	NPC9609
0.8704	High Similarity	NPC204854
0.8704	High Similarity	NPC152166
0.8704	High Similarity	NPC55738
0.8704	High Similarity	NPC130894
0.8704	High Similarity	NPC100123
0.8704	High Similarity	NPC7846
0.8704	High Similarity	NPC300943
0.8704	High Similarity	NPC143828
0.8704	High Similarity	NPC115798
0.8704	High Similarity	NPC191459
0.8704	High Similarity	NPC25495
0.8704	High Similarity	NPC261004
0.8704	High Similarity	NPC19687
0.8704	High Similarity	NPC253634
0.8704	High Similarity	NPC18772
0.8704	High Similarity	NPC195832
0.8696	High Similarity	NPC43243
0.8696	High Similarity	NPC13858
0.8696	High Similarity	NPC303255
0.8696	High Similarity	NPC292107
0.8696	High Similarity	NPC474520
0.8696	High Similarity	NPC201837
0.8696	High Similarity	NPC268161
0.8696	High Similarity	NPC320825
0.8696	High Similarity	NPC235165
0.8696	High Similarity	NPC55619
0.8696	High Similarity	NPC471500
0.8696	High Similarity	NPC245546
0.8696	High Similarity	NPC200388
0.8696	High Similarity	NPC49824
0.8696	High Similarity	NPC24640
0.8696	High Similarity	NPC266960
0.8696	High Similarity	NPC326037
0.8696	High Similarity	NPC250922
0.8696	High Similarity	NPC100916
0.8696	High Similarity	NPC255106
0.8688	High Similarity	NPC89474
0.8688	High Similarity	NPC477048
0.8688	High Similarity	NPC124714
0.8688	High Similarity	NPC250557
0.8688	High Similarity	NPC477047
0.8679	High Similarity	NPC45291
0.8679	High Similarity	NPC19980
0.8671	High Similarity	NPC102003
0.8671	High Similarity	NPC92722
0.8667	High Similarity	NPC472450
0.8667	High Similarity	NPC275780
0.8667	High Similarity	NPC239752
0.8667	High Similarity	NPC62261
0.8662	High Similarity	NPC210320
0.8662	High Similarity	NPC61871
0.8662	High Similarity	NPC55557
0.8662	High Similarity	NPC30647
0.8659	High Similarity	NPC25152
0.865	High Similarity	NPC36217
0.865	High Similarity	NPC475886
0.865	High Similarity	NPC470326
0.865	High Similarity	NPC287328
0.865	High Similarity	NPC320359
0.865	High Similarity	NPC139036
0.865	High Similarity	NPC282009
0.865	High Similarity	NPC474287
0.8642	High Similarity	NPC305663
0.8642	High Similarity	NPC472910
0.8642	High Similarity	NPC472913
0.8642	High Similarity	NPC245758
0.8642	High Similarity	NPC67876
0.8642	High Similarity	NPC227192
0.8642	High Similarity	NPC163524
0.8642	High Similarity	NPC176665
0.8642	High Similarity	NPC224137
0.8642	High Similarity	NPC217677
0.8642	High Similarity	NPC287979
0.8642	High Similarity	NPC96167
0.8642	High Similarity	NPC93376
0.8642	High Similarity	NPC165977
0.8642	High Similarity	NPC222814
0.8642	High Similarity	NPC78103
0.8642	High Similarity	NPC99597
0.8642	High Similarity	NPC246466
0.8642	High Similarity	NPC189179
0.8642	High Similarity	NPC472914
0.8642	High Similarity	NPC75215
0.8642	High Similarity	NPC223787
0.8642	High Similarity	NPC52530
0.8642	High Similarity	NPC210084
0.8642	High Similarity	NPC472911
0.8634	High Similarity	NPC472048
0.8634	High Similarity	NPC189960
0.8634	High Similarity	NPC213622
0.8634	High Similarity	NPC130589
0.8634	High Similarity	NPC134287
0.8634	High Similarity	NPC201451
0.8634	High Similarity	NPC26227
0.8634	High Similarity	NPC68727
0.8634	High Similarity	NPC32557
0.8634	High Similarity	NPC80534
0.8634	High Similarity	NPC234485
0.8634	High Similarity	NPC67396
0.8634	High Similarity	NPC56786

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 NPC48860 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	1068
0.2-0.3	2201
0.3-0.4	2613
0.4-0.5	1602
0.5-0.6	853
0.6-0.7	320
0.7-0.8	105
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.858	High Similarity	NPD3882	Suspended
0.8571	High Similarity	NPD2801	Approved
0.8509	High Similarity	NPD1934	Approved
0.8443	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6166	Phase 2
0.8344	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3817	Phase 2
0.8137	Intermediate Similarity	NPD1512	Approved
0.8129	Intermediate Similarity	NPD3818	Discontinued
0.8092	Intermediate Similarity	NPD6797	Phase 2
0.8046	Intermediate Similarity	NPD7251	Discontinued
0.8035	Intermediate Similarity	NPD7074	Phase 3
0.8012	Intermediate Similarity	NPD1511	Approved
0.8	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD7808	Phase 3
0.7988	Intermediate Similarity	NPD5494	Approved
0.7977	Intermediate Similarity	NPD7054	Approved
0.7965	Intermediate Similarity	NPD7473	Discontinued
0.7963	Intermediate Similarity	NPD2533	Approved
0.7963	Intermediate Similarity	NPD2532	Approved
0.7963	Intermediate Similarity	NPD2534	Approved
0.7962	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4380	Phase 2
0.7931	Intermediate Similarity	NPD7472	Approved
0.7925	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD5844	Phase 1
0.787	Intermediate Similarity	NPD7075	Discontinued
0.7857	Intermediate Similarity	NPD5402	Approved
0.7853	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1247	Approved
0.7816	Intermediate Similarity	NPD3751	Discontinued
0.7798	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3787	Discontinued
0.7791	Intermediate Similarity	NPD6799	Approved
0.7784	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD230	Phase 1
0.7747	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6801	Discontinued
0.7725	Intermediate Similarity	NPD6599	Discontinued
0.7692	Intermediate Similarity	NPD1465	Phase 2
0.767	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6959	Discontinued
0.7625	Intermediate Similarity	NPD1510	Phase 2
0.7595	Intermediate Similarity	NPD943	Approved
0.7595	Intermediate Similarity	NPD1240	Approved
0.7593	Intermediate Similarity	NPD1549	Phase 2
0.7588	Intermediate Similarity	NPD7819	Suspended
0.7561	Intermediate Similarity	NPD6190	Approved
0.7543	Intermediate Similarity	NPD3926	Phase 2
0.7541	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.7514	Intermediate Similarity	NPD6234	Discontinued
0.7514	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD1607	Approved
0.7473	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2796	Approved
0.7442	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5403	Approved
0.7439	Intermediate Similarity	NPD2800	Approved
0.7427	Intermediate Similarity	NPD37	Approved
0.7399	Intermediate Similarity	NPD4966	Approved
0.7399	Intermediate Similarity	NPD4965	Approved
0.7399	Intermediate Similarity	NPD4967	Phase 2
0.7389	Intermediate Similarity	NPD9494	Approved
0.7368	Intermediate Similarity	NPD6777	Approved
0.7368	Intermediate Similarity	NPD6780	Approved
0.7368	Intermediate Similarity	NPD6776	Approved
0.7368	Intermediate Similarity	NPD6778	Approved
0.7368	Intermediate Similarity	NPD6781	Approved
0.7368	Intermediate Similarity	NPD6782	Approved
0.7368	Intermediate Similarity	NPD6779	Approved
0.7362	Intermediate Similarity	NPD2935	Discontinued
0.7345	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7435	Discontinued
0.7329	Intermediate Similarity	NPD447	Suspended
0.7321	Intermediate Similarity	NPD5401	Approved
0.7321	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7228	Approved
0.7289	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5710	Approved
0.7288	Intermediate Similarity	NPD5711	Approved
0.7267	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD3749	Approved
0.7253	Intermediate Similarity	NPD6559	Discontinued
0.7253	Intermediate Similarity	NPD7685	Pre-registration
0.7243	Intermediate Similarity	NPD8150	Discontinued
0.7232	Intermediate Similarity	NPD7199	Phase 2
0.7207	Intermediate Similarity	NPD2403	Approved
0.7195	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1653	Approved
0.7186	Intermediate Similarity	NPD4628	Phase 3
0.7186	Intermediate Similarity	NPD3750	Approved
0.7178	Intermediate Similarity	NPD6651	Approved
0.7168	Intermediate Similarity	NPD7411	Suspended
0.7165	Intermediate Similarity	NPD7698	Approved
0.7165	Intermediate Similarity	NPD7696	Phase 3
0.7165	Intermediate Similarity	NPD7697	Approved
0.7152	Intermediate Similarity	NPD6100	Approved
0.7152	Intermediate Similarity	NPD6099	Approved
0.7151	Intermediate Similarity	NPD8434	Phase 2
0.7135	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7871	Phase 2
0.7128	Intermediate Similarity	NPD7870	Phase 2
0.7121	Intermediate Similarity	NPD7874	Approved
0.7121	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7701	Phase 2
0.7105	Intermediate Similarity	NPD6534	Approved
0.7105	Intermediate Similarity	NPD6535	Approved
0.7098	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD9269	Phase 2
0.7063	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7390	Discontinued
0.7045	Intermediate Similarity	NPD5353	Approved
0.7019	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4111	Phase 1
0.7006	Intermediate Similarity	NPD7768	Phase 2
0.7	Intermediate Similarity	NPD7801	Approved
0.6995	Remote Similarity	NPD7700	Phase 2
0.6995	Remote Similarity	NPD7699	Phase 2
0.6985	Remote Similarity	NPD8151	Discontinued
0.6971	Remote Similarity	NPD5089	Approved
0.6971	Remote Similarity	NPD5090	Approved
0.6961	Remote Similarity	NPD5242	Approved
0.6959	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3226	Approved
0.6946	Remote Similarity	NPD1551	Phase 2
0.6942	Remote Similarity	NPD7907	Approved
0.6939	Remote Similarity	NPD6823	Phase 2
0.6936	Remote Similarity	NPD920	Approved
0.6933	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4665	Approved
0.6923	Remote Similarity	NPD2654	Approved
0.6918	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2344	Approved
0.6898	Remote Similarity	NPD8312	Approved
0.6898	Remote Similarity	NPD8313	Approved
0.6888	Remote Similarity	NPD2493	Approved
0.6888	Remote Similarity	NPD2494	Approved
0.6886	Remote Similarity	NPD3748	Approved
0.6882	Remote Similarity	NPD7240	Approved
0.6882	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4582	Approved
0.6869	Remote Similarity	NPD4583	Approved
0.6856	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4060	Phase 1
0.6848	Remote Similarity	NPD2163	Approved
0.6845	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7783	Phase 2
0.6832	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5953	Discontinued
0.6824	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1243	Approved
0.6821	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4002	Approved
0.6818	Remote Similarity	NPD4004	Approved
0.6815	Remote Similarity	NPD9268	Approved
0.6811	Remote Similarity	NPD7286	Phase 2
0.6807	Remote Similarity	NPD6355	Discontinued
0.6805	Remote Similarity	NPD2346	Discontinued
0.6802	Remote Similarity	NPD3300	Phase 2
0.6802	Remote Similarity	NPD3452	Approved
0.6802	Remote Similarity	NPD3450	Approved
0.6788	Remote Similarity	NPD6233	Phase 2
0.6786	Remote Similarity	NPD2799	Discontinued
0.6784	Remote Similarity	NPD8320	Phase 1
0.6784	Remote Similarity	NPD8319	Approved
0.6779	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2424	Discontinued
0.675	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2309	Approved
0.6727	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6798	Discontinued
0.6706	Remote Similarity	NPD1471	Phase 3
0.6705	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD4585	Approved
0.6702	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3705	Approved
0.6686	Remote Similarity	NPD7033	Discontinued
0.6685	Remote Similarity	NPD6385	Approved
0.6685	Remote Similarity	NPD6386	Approved
0.6684	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2974	Approved
0.6684	Remote Similarity	NPD2975	Approved
0.6684	Remote Similarity	NPD2973	Approved
0.6667	Remote Similarity	NPD4580	Approved
0.6667	Remote Similarity	NPD4363	Phase 3
0.6667	Remote Similarity	NPD4360	Phase 2
0.6648	Remote Similarity	NPD6844	Discontinued
0.6647	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3620	Phase 2
0.6646	Remote Similarity	NPD9717	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