NPASS Compound

Structure

NPC472404 OpenBabel07101718182D 24 25 0 0 1 0 0 0 0 0999 V2000 -4.1980 -2.1248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6072 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4392 -3.4392 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 -3.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.7321 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 -3.2321 -1.8660 0.0000 C 0 0 3 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 -2.7321 -2.7321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.2321 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 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.3660 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6072 -4.1980 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 12 1 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 10 18 1 0 0 0 0 11 24 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.11
Volume:	346.115
LogP:	4.339
LogD:	3.544
LogS:	-3.974
# Rotatable Bonds:	0
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.694
Synthetic Accessibility Score:	4.332
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.773
MDCK Permeability:	2.464394856360741e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.318
Plasma Protein Binding (PPB):	98.67706298828125%
Volume Distribution (VD):	0.539
Pgp-substrate:	1.4348074197769165%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.861
CYP2C19-inhibitor:	0.764
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.887
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.876
CYP2D6-substrate:	0.205
CYP3A4-inhibitor:	0.682
CYP3A4-substrate:	0.276

ADMET: Excretion

Clearance (CL):	11.697
Half-life (T1/2):	0.774

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.301
Drug-inuced Liver Injury (DILI):	0.774
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.297
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.652
Carcinogencity:	0.475
Eye Corrosion:	0.004
Eye Irritation:	0.121
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC472404

Natural Product ID:	NPC472404
*Common Name:**	SQFBFKKGAWCQAU-UXBLZVDNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SQFBFKKGAWCQAU-UXBLZVDNSA-N
Standard InCHI:	InChI=1S/C18H21ClO5/c1-9-5-4-6-10(2)18(23)16-12(7-15(22)24-11(9)3)17(19)14(21)8-13(16)20/h6,8-9,11,20-21H,4-5,7H2,1-3H3/b10-6+
SMILES:	CC1CCC=C(C(=O)C2=C(CC(=O)OC1C)C(=C(C=C2O)O)Cl)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3400935
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO30056	Exserohilum rostratum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332857]
NPO30056	Exserohilum rostratum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18774863]
NPO30056	Exserohilum rostratum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25537529]

☑ 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	2
Others	1

Activity Type	# Activity
Cell Line	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	>	70.0	%	PMID[452394]
NPT2	Others	Unspecified		IC50	=	210.0	nM	PMID[452394]
NPT2	Others	Unspecified		IC50	=	336.0	nM	PMID[452394]

☑ 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 NPC472404 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	367
0.1-0.2	1763
0.2-0.3	4772
0.3-0.4	11770
0.4-0.5	7876
0.5-0.6	6972
0.6-0.7	7659
0.7-0.8	1433
0.8-0.85	54
0.85-0.9	14
0.9-0.95	13
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9673	High Similarity	NPC472405
0.9673	High Similarity	NPC298401
0.961	High Similarity	NPC473696
0.9487	High Similarity	NPC173352
0.9487	High Similarity	NPC58653
0.9427	High Similarity	NPC28669
0.9427	High Similarity	NPC474061
0.9423	High Similarity	NPC470081
0.9367	High Similarity	NPC472032
0.9359	High Similarity	NPC474096
0.8792	High Similarity	NPC472403
0.8766	High Similarity	NPC477569
0.8667	High Similarity	NPC9121
0.8667	High Similarity	NPC177307
0.8654	High Similarity	NPC477567
0.8654	High Similarity	NPC477566
0.86	High Similarity	NPC474771
0.86	High Similarity	NPC149372
0.86	High Similarity	NPC474849
0.86	High Similarity	NPC65837
0.86	High Similarity	NPC178467
0.8543	High Similarity	NPC475974
0.8497	Intermediate Similarity	NPC478201
0.8497	Intermediate Similarity	NPC472035
0.8452	Intermediate Similarity	NPC470422
0.8447	Intermediate Similarity	NPC280497
0.8415	Intermediate Similarity	NPC245122
0.8382	Intermediate Similarity	NPC470103
0.8377	Intermediate Similarity	NPC313123
0.8377	Intermediate Similarity	NPC478217
0.8366	Intermediate Similarity	NPC474655
0.8333	Intermediate Similarity	NPC126882
0.8333	Intermediate Similarity	NPC478203
0.8333	Intermediate Similarity	NPC210966
0.8324	Intermediate Similarity	NPC99937
0.8301	Intermediate Similarity	NPC33144
0.8301	Intermediate Similarity	NPC191835
0.8301	Intermediate Similarity	NPC478200
0.8284	Intermediate Similarity	NPC474857
0.828	Intermediate Similarity	NPC257558
0.828	Intermediate Similarity	NPC472034
0.8269	Intermediate Similarity	NPC354984
0.8269	Intermediate Similarity	NPC478202
0.8253	Intermediate Similarity	NPC470563
0.8249	Intermediate Similarity	NPC221185
0.8239	Intermediate Similarity	NPC470100
0.8235	Intermediate Similarity	NPC70380
0.8232	Intermediate Similarity	NPC470559
0.8228	Intermediate Similarity	NPC472033
0.8225	Intermediate Similarity	NPC277865
0.8202	Intermediate Similarity	NPC247104
0.8193	Intermediate Similarity	NPC470561
0.8187	Intermediate Similarity	NPC264922
0.8182	Intermediate Similarity	NPC94248
0.8182	Intermediate Similarity	NPC212693
0.8176	Intermediate Similarity	NPC472036
0.8171	Intermediate Similarity	NPC197326
0.815	Intermediate Similarity	NPC471801
0.8136	Intermediate Similarity	NPC470099
0.8129	Intermediate Similarity	NPC92655
0.8121	Intermediate Similarity	NPC41263
0.8117	Intermediate Similarity	NPC71256
0.811	Intermediate Similarity	NPC470564
0.8092	Intermediate Similarity	NPC153783
0.8079	Intermediate Similarity	NPC136411
0.8079	Intermediate Similarity	NPC316091
0.8077	Intermediate Similarity	NPC158472
0.8065	Intermediate Similarity	NPC472602
0.8056	Intermediate Similarity	NPC48822
0.8052	Intermediate Similarity	NPC235115
0.8038	Intermediate Similarity	NPC472006
0.8035	Intermediate Similarity	NPC45072
0.8025	Intermediate Similarity	NPC53649
0.8025	Intermediate Similarity	NPC244923
0.8025	Intermediate Similarity	NPC1704
0.8025	Intermediate Similarity	NPC158634
0.8025	Intermediate Similarity	NPC472603
0.8025	Intermediate Similarity	NPC67650
0.8013	Intermediate Similarity	NPC268052
0.8013	Intermediate Similarity	NPC32360
0.8013	Intermediate Similarity	NPC139634
0.8013	Intermediate Similarity	NPC52358
0.8013	Intermediate Similarity	NPC105456
0.8012	Intermediate Similarity	NPC471641
0.8012	Intermediate Similarity	NPC471642
0.8012	Intermediate Similarity	NPC470562
0.8012	Intermediate Similarity	NPC240622
0.8012	Intermediate Similarity	NPC240253
0.8	Intermediate Similarity	NPC151292
0.8	Intermediate Similarity	NPC214901
0.7978	Intermediate Similarity	NPC108744
0.7978	Intermediate Similarity	NPC313386
0.7977	Intermediate Similarity	NPC477568
0.7975	Intermediate Similarity	NPC474385
0.7974	Intermediate Similarity	NPC43627
0.7966	Intermediate Similarity	NPC191606
0.7965	Intermediate Similarity	NPC470560
0.7962	Intermediate Similarity	NPC472601
0.7962	Intermediate Similarity	NPC472600
0.7961	Intermediate Similarity	NPC219892
0.7961	Intermediate Similarity	NPC189823
0.7944	Intermediate Similarity	NPC220369
0.7937	Intermediate Similarity	NPC312789
0.7925	Intermediate Similarity	NPC51106
0.7925	Intermediate Similarity	NPC159721
0.7922	Intermediate Similarity	NPC474097
0.7919	Intermediate Similarity	NPC262671
0.7919	Intermediate Similarity	NPC201728
0.7911	Intermediate Similarity	NPC472605
0.7911	Intermediate Similarity	NPC472604
0.7911	Intermediate Similarity	NPC475730
0.7907	Intermediate Similarity	NPC470565
0.7901	Intermediate Similarity	NPC215711
0.7901	Intermediate Similarity	NPC73411
0.7898	Intermediate Similarity	NPC88269
0.7898	Intermediate Similarity	NPC162939
0.7895	Intermediate Similarity	NPC17840
0.7895	Intermediate Similarity	NPC247477
0.7888	Intermediate Similarity	NPC107625
0.7885	Intermediate Similarity	NPC135837
0.7885	Intermediate Similarity	NPC194579
0.7882	Intermediate Similarity	NPC68850
0.7877	Intermediate Similarity	NPC471812
0.7877	Intermediate Similarity	NPC471804
0.7877	Intermediate Similarity	NPC471803
0.7875	Intermediate Similarity	NPC277426
0.7875	Intermediate Similarity	NPC151607
0.7875	Intermediate Similarity	NPC86373
0.7875	Intermediate Similarity	NPC280404
0.7875	Intermediate Similarity	NPC42540
0.7875	Intermediate Similarity	NPC210425
0.7857	Intermediate Similarity	NPC48036
0.7843	Intermediate Similarity	NPC320819
0.7841	Intermediate Similarity	NPC306240
0.784	Intermediate Similarity	NPC210320
0.7833	Intermediate Similarity	NPC39409
0.7826	Intermediate Similarity	NPC473692
0.7826	Intermediate Similarity	NPC83272
0.7826	Intermediate Similarity	NPC154720
0.7821	Intermediate Similarity	NPC475955
0.7821	Intermediate Similarity	NPC474499
0.7821	Intermediate Similarity	NPC474726
0.7818	Intermediate Similarity	NPC213224
0.7814	Intermediate Similarity	NPC313541
0.7812	Intermediate Similarity	NPC469542
0.7812	Intermediate Similarity	NPC471731
0.7812	Intermediate Similarity	NPC472610
0.7806	Intermediate Similarity	NPC474394
0.7806	Intermediate Similarity	NPC175943
0.7805	Intermediate Similarity	NPC56204
0.7803	Intermediate Similarity	NPC107283
0.78	Intermediate Similarity	NPC477454
0.7799	Intermediate Similarity	NPC37530
0.7791	Intermediate Similarity	NPC153417
0.779	Intermediate Similarity	NPC471810
0.779	Intermediate Similarity	NPC471807
0.779	Intermediate Similarity	NPC471806
0.7784	Intermediate Similarity	NPC471802
0.7778	Intermediate Similarity	NPC473023
0.7771	Intermediate Similarity	NPC55092
0.7771	Intermediate Similarity	NPC275837
0.7759	Intermediate Similarity	NPC188618
0.7756	Intermediate Similarity	NPC290803
0.7756	Intermediate Similarity	NPC27407
0.7756	Intermediate Similarity	NPC180905
0.7756	Intermediate Similarity	NPC278375
0.7756	Intermediate Similarity	NPC182496
0.775	Intermediate Similarity	NPC469579
0.775	Intermediate Similarity	NPC471640
0.775	Intermediate Similarity	NPC471733
0.775	Intermediate Similarity	NPC471644
0.7748	Intermediate Similarity	NPC473691
0.7744	Intermediate Similarity	NPC84142
0.7742	Intermediate Similarity	NPC37299
0.7742	Intermediate Similarity	NPC180261
0.7736	Intermediate Similarity	NPC99441
0.7736	Intermediate Similarity	NPC155205
0.7735	Intermediate Similarity	NPC121100
0.7735	Intermediate Similarity	NPC471805
0.7735	Intermediate Similarity	NPC471813
0.7733	Intermediate Similarity	NPC131078
0.773	Intermediate Similarity	NPC14098
0.7725	Intermediate Similarity	NPC478221
0.7725	Intermediate Similarity	NPC472890
0.7722	Intermediate Similarity	NPC221104
0.7717	Intermediate Similarity	NPC198163
0.7711	Intermediate Similarity	NPC76041
0.7711	Intermediate Similarity	NPC184284
0.7707	Intermediate Similarity	NPC158481
0.7702	Intermediate Similarity	NPC200207
0.7702	Intermediate Similarity	NPC471639
0.7702	Intermediate Similarity	NPC471643
0.7697	Intermediate Similarity	NPC472891
0.7697	Intermediate Similarity	NPC164762
0.7697	Intermediate Similarity	NPC60413
0.7692	Intermediate Similarity	NPC474519
0.7688	Intermediate Similarity	NPC470842
0.7688	Intermediate Similarity	NPC90411
0.7683	Intermediate Similarity	NPC221352
0.7679	Intermediate Similarity	NPC472623

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 NPC472404 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	1074
0.2-0.3	2010
0.3-0.4	2948
0.4-0.5	1860
0.5-0.6	735
0.6-0.7	204
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7785	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD2403	Approved
0.7394	Intermediate Similarity	NPD2533	Approved
0.7394	Intermediate Similarity	NPD2532	Approved
0.7394	Intermediate Similarity	NPD2534	Approved
0.7353	Intermediate Similarity	NPD7819	Suspended
0.7267	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD230	Phase 1
0.716	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7411	Suspended
0.711	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1510	Phase 2
0.703	Intermediate Similarity	NPD1549	Phase 2
0.7029	Intermediate Similarity	NPD7075	Discontinued
0.7024	Intermediate Similarity	NPD6799	Approved
0.7024	Intermediate Similarity	NPD7390	Discontinued
0.7019	Intermediate Similarity	NPD1240	Approved
0.7019	Intermediate Similarity	NPD943	Approved
0.6983	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3750	Approved
0.6944	Remote Similarity	NPD7473	Discontinued
0.6933	Remote Similarity	NPD1607	Approved
0.6928	Remote Similarity	NPD9545	Approved
0.691	Remote Similarity	NPD6959	Discontinued
0.6909	Remote Similarity	NPD5404	Approved
0.6909	Remote Similarity	NPD5405	Approved
0.6909	Remote Similarity	NPD5406	Approved
0.6909	Remote Similarity	NPD2796	Approved
0.6909	Remote Similarity	NPD5408	Approved
0.6897	Remote Similarity	NPD1934	Approved
0.6895	Remote Similarity	NPD4363	Phase 3
0.6895	Remote Similarity	NPD4360	Phase 2
0.6882	Remote Similarity	NPD1578	Phase 2
0.6882	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4380	Phase 2
0.6879	Remote Similarity	NPD6599	Discontinued
0.6875	Remote Similarity	NPD3882	Suspended
0.6872	Remote Similarity	NPD6232	Discontinued
0.6839	Remote Similarity	NPD958	Approved
0.6836	Remote Similarity	NPD3749	Approved
0.6818	Remote Similarity	NPD3817	Phase 2
0.6815	Remote Similarity	NPD9269	Phase 2
0.6807	Remote Similarity	NPD2935	Discontinued
0.6807	Remote Similarity	NPD1551	Phase 2
0.68	Remote Similarity	NPD6801	Discontinued
0.6797	Remote Similarity	NPD9493	Approved
0.6788	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7768	Phase 2
0.678	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5710	Approved
0.6778	Remote Similarity	NPD5711	Approved
0.6774	Remote Similarity	NPD9268	Approved
0.6771	Remote Similarity	NPD4361	Phase 2
0.6771	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD957	Approved
0.6761	Remote Similarity	NPD2801	Approved
0.6742	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1511	Approved
0.6724	Remote Similarity	NPD3226	Approved
0.6708	Remote Similarity	NPD454	Approved
0.6688	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1470	Approved
0.6686	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5844	Phase 1
0.6647	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1512	Approved
0.6647	Remote Similarity	NPD3748	Approved
0.6646	Remote Similarity	NPD1201	Approved
0.663	Remote Similarity	NPD3818	Discontinued
0.6629	Remote Similarity	NPD5402	Approved
0.6627	Remote Similarity	NPD6651	Approved
0.6612	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6166	Phase 2
0.6612	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5403	Approved
0.66	Remote Similarity	NPD74	Approved
0.66	Remote Similarity	NPD9266	Approved
0.6595	Remote Similarity	NPD7054	Approved
0.6588	Remote Similarity	NPD1243	Approved
0.6588	Remote Similarity	NPD2800	Approved
0.6585	Remote Similarity	NPD3764	Approved
0.6584	Remote Similarity	NPD1164	Approved
0.6575	Remote Similarity	NPD5494	Approved
0.6559	Remote Similarity	NPD7472	Approved
0.6559	Remote Similarity	NPD7074	Phase 3
0.655	Remote Similarity	NPD4628	Phase 3
0.6548	Remote Similarity	NPD2799	Discontinued
0.6543	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD9264	Approved
0.6533	Remote Similarity	NPD9263	Approved
0.6533	Remote Similarity	NPD9267	Approved
0.6533	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5953	Discontinued
0.6524	Remote Similarity	NPD6797	Phase 2
0.6514	Remote Similarity	NPD920	Approved
0.6512	Remote Similarity	NPD3887	Approved
0.6509	Remote Similarity	NPD6100	Approved
0.6509	Remote Similarity	NPD6099	Approved
0.65	Remote Similarity	NPD9717	Approved
0.6494	Remote Similarity	NPD5401	Approved
0.6492	Remote Similarity	NPD8150	Discontinued
0.6489	Remote Similarity	NPD6559	Discontinued
0.6489	Remote Similarity	NPD7251	Discontinued
0.648	Remote Similarity	NPD4915	Approved
0.648	Remote Similarity	NPD1465	Phase 2
0.6474	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4914	Approved
0.6456	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7808	Phase 3
0.6443	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD919	Approved
0.6417	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7286	Phase 2
0.6416	Remote Similarity	NPD6190	Approved
0.6416	Remote Similarity	NPD2354	Approved
0.6404	Remote Similarity	NPD4972	Discontinued
0.64	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.64	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2654	Approved
0.6386	Remote Similarity	NPD411	Approved
0.6386	Remote Similarity	NPD3268	Approved
0.638	Remote Similarity	NPD1203	Approved
0.6374	Remote Similarity	NPD2346	Discontinued
0.6369	Remote Similarity	NPD447	Suspended
0.6364	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6832	Phase 2
0.6348	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD6663	Approved
0.6347	Remote Similarity	NPD520	Approved
0.6346	Remote Similarity	NPD9281	Approved
0.6345	Remote Similarity	NPD4931	Phase 2
0.6339	Remote Similarity	NPD6234	Discontinued
0.6333	Remote Similarity	NPD37	Approved
0.6328	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD4966	Approved
0.6319	Remote Similarity	NPD4965	Approved
0.6319	Remote Similarity	NPD4967	Phase 2
0.6318	Remote Similarity	NPD4386	Approved
0.6318	Remote Similarity	NPD4387	Approved
0.6313	Remote Similarity	NPD4388	Approved
0.6307	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5736	Approved
0.6294	Remote Similarity	NPD6312	Discontinued
0.6283	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD2344	Approved
0.6279	Remote Similarity	NPD2353	Approved
0.6279	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD1184	Approved
0.627	Remote Similarity	NPD7199	Phase 2
0.627	Remote Similarity	NPD1247	Approved
0.6269	Remote Similarity	NPD6785	Approved
0.6269	Remote Similarity	NPD6784	Approved
0.6267	Remote Similarity	NPD9261	Approved
0.6264	Remote Similarity	NPD5353	Approved
0.6264	Remote Similarity	NPD8166	Discontinued
0.6256	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5544	Approved
0.625	Remote Similarity	NPD8312	Approved
0.625	Remote Similarity	NPD8313	Approved
0.6242	Remote Similarity	NPD2798	Approved
0.6237	Remote Similarity	NPD7229	Phase 3
0.6235	Remote Similarity	NPD422	Phase 1
0.6234	Remote Similarity	NPD4750	Phase 3
0.6219	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD8151	Discontinued
0.6203	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD3926	Phase 2
0.62	Remote Similarity	NPD4974	Approved
0.62	Remote Similarity	NPD4975	Approved
0.6196	Remote Similarity	NPD4878	Approved
0.6196	Remote Similarity	NPD1608	Approved
0.6193	Remote Similarity	NPD3300	Phase 2
0.619	Remote Similarity	NPD3751	Discontinued
0.618	Remote Similarity	NPD6273	Approved
0.6176	Remote Similarity	NPD8320	Phase 1
0.6176	Remote Similarity	NPD8319	Approved
0.6175	Remote Similarity	NPD4288	Approved
0.6171	Remote Similarity	NPD7003	Approved
0.6167	Remote Similarity	NPD7458	Discontinued
0.6163	Remote Similarity	NPD7033	Discontinued
0.6163	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD7041	Phase 2
0.6154	Remote Similarity	NPD8434	Phase 2
0.615	Remote Similarity	NPD5543	Approved
0.6149	Remote Similarity	NPD5958	Discontinued
0.6149	Remote Similarity	NPD4534	Discontinued
0.6146	Remote Similarity	NPD3658	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