NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1298.61
Volume:	1213.265
LogP:	-0.924
LogD:	0.098
LogS:	-2.208
# Rotatable Bonds:	13
TPSA:	482.74
# H-Bond Aceptor:	30
# H-Bond Donor:	18
# Rings:	11
# Heavy Atoms:	30

MedChem Properties

QED Drug-Likeness Score:	0.077
Synthetic Accessibility Score:	7.663
Fsp3:	0.983
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:	-6.7
MDCK Permeability:	0.0007377418805845082
Pgp-inhibitor:	0.841
Pgp-substrate:	0.892
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.267
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.328
Plasma Protein Binding (PPB):	39.10387420654297%
Volume Distribution (VD):	-0.308
Pgp-substrate:	20.06757164001465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	-0.577
Half-life (T1/2):	0.705

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.88
Skin Sensitization:	0.022
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.293

Download Data

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

Natural Product: NPC477465

Natural Product ID:	NPC477465
*Common Name:**	(3S,5S,6R)-4-[(2S,3S,5R)-3-[(4S,6S)-4,5-dihydroxy-6-methyl-3-[(3S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-6-[[(1R,2R,4S,5R,10S,13R,17S,21R,22R,23S)-2,21,22,23-tetrahydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-10-yl]oxy]-5-[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
IUPAC Name:	(3S,5S,6R)-4-[(2S,3S,5R)-3-[(4S,6S)-4,5-dihydroxy-6-methyl-3-[(3S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-6-[[(1R,2R,4S,5R,10S,13R,17S,21R,22R,23S)-2,21,22,23-tetrahydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-10-yl]oxy]-5-[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms:
Standard InCHIKey:	MFFNPNFZJAQCRY-UJEMSRJFSA-N
Standard InCHI:	InChI=1S/C60H98O30/c1-20-29(64)33(68)37(72)48(80-20)87-42-35(70)30(65)21(2)81-50(42)88-43-36(71)32(67)23(19-62)83-51(43)85-40-39(74)41(47(77)78)86-52(44(40)89-49-38(73)34(69)31(66)22(18-61)82-49)84-28-12-13-56(7)24(55(28,5)6)10-14-57(8)25(56)11-15-59-26-16-54(3,4)45(75)46(76)60(26,53(79)90-59)27(63)17-58(57,59)9/h20-46,48-53,61-76,79H,10-19H2,1-9H3,(H,77,78)/t20-,21-,22?,23?,24?,25?,26?,27+,28-,29-,30?,31+,32-,33?,34?,35-,36?,37-,38-,39-,40?,41?,42?,43-,44-,45-,46-,48?,49-,50?,51-,52+,53-,56-,57+,58-,59-,60+/m0/s1
SMILES:	C[C@H]1[C@@H](C([C@@H](C(O1)OC2[C@H](C([C@@H](OC2O[C@@H]3[C@@H](OC([C@@H](C3O)O)CO)OC4[C@@H]([C@@H](OC([C@H]4O)C(=O)O)O[C@H]5CC[C@@]6(C7CC[C@]89C1CC([C@H]([C@@H]([C@@]1([C@@H](C[C@]8([C@@]7(CCC6C5(C)C)C)C)O)[C@H](O9)O)O)O)(C)C)C)O[C@H]1[C@H](C([C@@H](C(O1)CO)O)O)O)C)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44388619
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO22350	Maesa balansae	Species	Primulaceae	Eukaryota	Leaves	Deo Khe, Dai Tu district, Thai Nguyen province in Vietnam	2000-NOV	PMID[15633999]
NPO22350	Maesa balansae	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	CC50	>	32	ug/ml	PMID[15633999]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	IC50	>	32	ug/ml	PMID[15633999]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	IC90	>	32	ug/ml	PMID[15633999]

☑ 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 NPC477465 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	566
0.1-0.2	4028
0.2-0.3	9143
0.3-0.4	12516
0.4-0.5	7580
0.5-0.6	4518
0.6-0.7	2436
0.7-0.8	1523
0.8-0.85	316
0.85-0.9	52
0.9-0.95	18
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.934	High Similarity	NPC22709
0.9259	High Similarity	NPC157571
0.9252	High Similarity	NPC470622
0.9245	High Similarity	NPC207693
0.9151	High Similarity	NPC126753
0.9074	High Similarity	NPC471431
0.8972	High Similarity	NPC471430
0.8929	High Similarity	NPC179429
0.8899	High Similarity	NPC66513
0.8889	High Similarity	NPC471626
0.8889	High Similarity	NPC473688
0.8889	High Similarity	NPC262567
0.8889	High Similarity	NPC231566
0.8879	High Similarity	NPC273189
0.8879	High Similarity	NPC184805
0.8807	High Similarity	NPC87393
0.8807	High Similarity	NPC236753
0.8807	High Similarity	NPC228190
0.8796	High Similarity	NPC475234
0.8796	High Similarity	NPC475630
0.8796	High Similarity	NPC40716
0.8796	High Similarity	NPC138219
0.8785	High Similarity	NPC267637
0.8762	High Similarity	NPC471428
0.8762	High Similarity	NPC51579
0.8762	High Similarity	NPC471426
0.8762	High Similarity	NPC471427
0.8716	High Similarity	NPC469826
0.8704	High Similarity	NPC158051
0.8704	High Similarity	NPC158367
0.8704	High Similarity	NPC119628
0.8667	High Similarity	NPC471374
0.8667	High Similarity	NPC471375
0.8667	High Similarity	NPC209798
0.8649	High Similarity	NPC469824
0.8624	High Similarity	NPC203974
0.8598	High Similarity	NPC80640
0.8487	Intermediate Similarity	NPC470218
0.8462	Intermediate Similarity	NPC470478
0.844	Intermediate Similarity	NPC469827
0.8411	Intermediate Similarity	NPC80417
0.8403	Intermediate Similarity	NPC23275
0.8403	Intermediate Similarity	NPC33068
0.839	Intermediate Similarity	NPC131469
0.839	Intermediate Similarity	NPC313110
0.8381	Intermediate Similarity	NPC471424
0.8381	Intermediate Similarity	NPC471429
0.8381	Intermediate Similarity	NPC205129
0.8381	Intermediate Similarity	NPC106701
0.8381	Intermediate Similarity	NPC189575
0.8381	Intermediate Similarity	NPC471425
0.8319	Intermediate Similarity	NPC478066
0.8319	Intermediate Similarity	NPC200049
0.8319	Intermediate Similarity	NPC302543
0.8319	Intermediate Similarity	NPC283417
0.8319	Intermediate Similarity	NPC235405
0.8319	Intermediate Similarity	NPC258617
0.8319	Intermediate Similarity	NPC281148
0.8319	Intermediate Similarity	NPC30735
0.8319	Intermediate Similarity	NPC257211
0.8305	Intermediate Similarity	NPC302887
0.8305	Intermediate Similarity	NPC187618
0.8304	Intermediate Similarity	NPC469825
0.8286	Intermediate Similarity	NPC253611
0.8286	Intermediate Similarity	NPC267238
0.8286	Intermediate Similarity	NPC148593
0.8286	Intermediate Similarity	NPC77717
0.8286	Intermediate Similarity	NPC471373
0.825	Intermediate Similarity	NPC470477
0.8235	Intermediate Similarity	NPC40775
0.8235	Intermediate Similarity	NPC187290
0.8235	Intermediate Similarity	NPC213952
0.8235	Intermediate Similarity	NPC475591
0.8235	Intermediate Similarity	NPC4749
0.8235	Intermediate Similarity	NPC249848
0.8235	Intermediate Similarity	NPC235438
0.8235	Intermediate Similarity	NPC107966
0.8235	Intermediate Similarity	NPC80986
0.8235	Intermediate Similarity	NPC10607
0.8235	Intermediate Similarity	NPC21691
0.8235	Intermediate Similarity	NPC236870
0.822	Intermediate Similarity	NPC236657
0.822	Intermediate Similarity	NPC118440
0.819	Intermediate Similarity	NPC323231
0.819	Intermediate Similarity	NPC171741
0.819	Intermediate Similarity	NPC18724
0.819	Intermediate Similarity	NPC224003
0.819	Intermediate Similarity	NPC470623
0.8182	Intermediate Similarity	NPC181066
0.8182	Intermediate Similarity	NPC475368
0.8182	Intermediate Similarity	NPC469947
0.8182	Intermediate Similarity	NPC273962
0.8182	Intermediate Similarity	NPC284449
0.8151	Intermediate Similarity	NPC104372
0.8151	Intermediate Similarity	NPC11242
0.8151	Intermediate Similarity	NPC159309
0.8151	Intermediate Similarity	NPC22956
0.8151	Intermediate Similarity	NPC51099
0.8151	Intermediate Similarity	NPC64715
0.8151	Intermediate Similarity	NPC275225
0.8151	Intermediate Similarity	NPC31838
0.8151	Intermediate Similarity	NPC293031
0.8151	Intermediate Similarity	NPC223301
0.8151	Intermediate Similarity	NPC171544
0.8151	Intermediate Similarity	NPC297263
0.8151	Intermediate Similarity	NPC114484
0.8151	Intermediate Similarity	NPC222580
0.8151	Intermediate Similarity	NPC86222
0.8151	Intermediate Similarity	NPC301449
0.8151	Intermediate Similarity	NPC62725
0.8151	Intermediate Similarity	NPC68767
0.8142	Intermediate Similarity	NPC473817
0.8142	Intermediate Similarity	NPC273002
0.8142	Intermediate Similarity	NPC220836
0.8142	Intermediate Similarity	NPC92297
0.8142	Intermediate Similarity	NPC94086
0.8142	Intermediate Similarity	NPC233433
0.8103	Intermediate Similarity	NPC79193
0.8099	Intermediate Similarity	NPC160452
0.8087	Intermediate Similarity	NPC477492
0.8087	Intermediate Similarity	NPC477489
0.8083	Intermediate Similarity	NPC162574
0.8067	Intermediate Similarity	NPC473645
0.8067	Intermediate Similarity	NPC267694
0.8067	Intermediate Similarity	NPC153673
0.8067	Intermediate Similarity	NPC144644
0.8067	Intermediate Similarity	NPC37860
0.8067	Intermediate Similarity	NPC110385
0.8067	Intermediate Similarity	NPC142151
0.8053	Intermediate Similarity	NPC202898
0.8053	Intermediate Similarity	NPC475319
0.8053	Intermediate Similarity	NPC92890
0.8049	Intermediate Similarity	NPC470476
0.8049	Intermediate Similarity	NPC470475
0.8033	Intermediate Similarity	NPC285091
0.8017	Intermediate Similarity	NPC44716
0.8017	Intermediate Similarity	NPC2370
0.8	Intermediate Similarity	NPC478154
0.8	Intermediate Similarity	NPC473062
0.8	Intermediate Similarity	NPC75417
0.7983	Intermediate Similarity	NPC192791
0.7983	Intermediate Similarity	NPC114441
0.7983	Intermediate Similarity	NPC471577
0.7983	Intermediate Similarity	NPC473884
0.7983	Intermediate Similarity	NPC208381
0.7983	Intermediate Similarity	NPC214484
0.7983	Intermediate Similarity	NPC35405
0.7983	Intermediate Similarity	NPC39211
0.7983	Intermediate Similarity	NPC157868
0.7983	Intermediate Similarity	NPC180550
0.7983	Intermediate Similarity	NPC309780
0.7983	Intermediate Similarity	NPC475171
0.7983	Intermediate Similarity	NPC469945
0.7983	Intermediate Similarity	NPC207738
0.7983	Intermediate Similarity	NPC11551
0.7983	Intermediate Similarity	NPC472949
0.7983	Intermediate Similarity	NPC477464
0.7983	Intermediate Similarity	NPC6377
0.7982	Intermediate Similarity	NPC472144
0.7966	Intermediate Similarity	NPC224121
0.7963	Intermediate Similarity	NPC475785
0.7963	Intermediate Similarity	NPC475765
0.7951	Intermediate Similarity	NPC471963
0.7951	Intermediate Similarity	NPC247315
0.7951	Intermediate Similarity	NPC471962
0.7946	Intermediate Similarity	NPC470167
0.7937	Intermediate Similarity	NPC478151
0.7928	Intermediate Similarity	NPC471254
0.792	Intermediate Similarity	NPC173435
0.792	Intermediate Similarity	NPC476775
0.792	Intermediate Similarity	NPC478155
0.792	Intermediate Similarity	NPC134914
0.792	Intermediate Similarity	NPC172374
0.792	Intermediate Similarity	NPC45346
0.792	Intermediate Similarity	NPC271610
0.792	Intermediate Similarity	NPC476780
0.792	Intermediate Similarity	NPC301639
0.792	Intermediate Similarity	NPC476074
0.792	Intermediate Similarity	NPC264566
0.792	Intermediate Similarity	NPC475167
0.792	Intermediate Similarity	NPC329993
0.792	Intermediate Similarity	NPC475377
0.792	Intermediate Similarity	NPC478064
0.792	Intermediate Similarity	NPC25998
0.792	Intermediate Similarity	NPC478065
0.792	Intermediate Similarity	NPC476774
0.792	Intermediate Similarity	NPC262796
0.7917	Intermediate Similarity	NPC476991
0.7899	Intermediate Similarity	NPC237191
0.7899	Intermediate Similarity	NPC475899
0.7899	Intermediate Similarity	NPC286347
0.7899	Intermediate Similarity	NPC105800
0.7899	Intermediate Similarity	NPC232237
0.7895	Intermediate Similarity	NPC472079
0.789	Intermediate Similarity	NPC472145
0.789	Intermediate Similarity	NPC74466
0.789	Intermediate Similarity	NPC470632
0.789	Intermediate Similarity	NPC472273
0.7886	Intermediate Similarity	NPC87662
0.7876	Intermediate Similarity	NPC215408

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 NPC477465 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	600
0.1-0.2	3979
0.2-0.3	3037
0.3-0.4	870
0.4-0.5	366
0.5-0.6	213
0.6-0.7	74
0.7-0.8	8
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.812	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD8328	Phase 3
0.7788	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD8133	Approved
0.7227	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8171	Discontinued
0.7143	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7329	Approved
0.6947	Remote Similarity	NPD7736	Approved
0.6875	Remote Similarity	NPD8517	Approved
0.6875	Remote Similarity	NPD8515	Approved
0.6875	Remote Similarity	NPD8516	Approved
0.678	Remote Similarity	NPD1700	Approved
0.6744	Remote Similarity	NPD8513	Phase 3
0.6742	Remote Similarity	NPD8293	Discontinued
0.6697	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD3669	Approved
0.6642	Remote Similarity	NPD7319	Approved
0.6615	Remote Similarity	NPD6921	Approved
0.6565	Remote Similarity	NPD6370	Approved
0.6541	Remote Similarity	NPD7507	Approved
0.6538	Remote Similarity	NPD8377	Approved
0.6538	Remote Similarity	NPD8294	Approved
0.6514	Remote Similarity	NPD1780	Approved
0.6514	Remote Similarity	NPD1779	Approved
0.6489	Remote Similarity	NPD8378	Approved
0.6489	Remote Similarity	NPD8380	Approved
0.6489	Remote Similarity	NPD8296	Approved
0.6489	Remote Similarity	NPD8379	Approved
0.6489	Remote Similarity	NPD8335	Approved
0.6475	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7492	Approved
0.6429	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD6616	Approved
0.6412	Remote Similarity	NPD6054	Approved
0.6412	Remote Similarity	NPD6059	Approved
0.637	Remote Similarity	NPD7078	Approved
0.6364	Remote Similarity	NPD8033	Approved
0.6357	Remote Similarity	NPD6940	Discontinued
0.6336	Remote Similarity	NPD7516	Approved
0.6311	Remote Similarity	NPD8084	Approved
0.6311	Remote Similarity	NPD8138	Approved
0.6311	Remote Similarity	NPD8082	Approved
0.6311	Remote Similarity	NPD8083	Approved
0.6311	Remote Similarity	NPD8139	Approved
0.6311	Remote Similarity	NPD8085	Approved
0.6311	Remote Similarity	NPD8086	Approved
0.629	Remote Similarity	NPD8393	Approved
0.6288	Remote Similarity	NPD6319	Approved
0.626	Remote Similarity	NPD7328	Approved
0.626	Remote Similarity	NPD7327	Approved
0.626	Remote Similarity	NPD8275	Approved
0.626	Remote Similarity	NPD8276	Approved
0.6241	Remote Similarity	NPD6015	Approved
0.6241	Remote Similarity	NPD6016	Approved
0.6239	Remote Similarity	NPD6697	Approved
0.6239	Remote Similarity	NPD6115	Approved
0.6239	Remote Similarity	NPD6118	Approved
0.6239	Remote Similarity	NPD6114	Approved
0.621	Remote Similarity	NPD8081	Approved
0.6194	Remote Similarity	NPD5988	Approved
0.619	Remote Similarity	NPD6686	Approved
0.6147	Remote Similarity	NPD6116	Phase 1
0.6126	Remote Similarity	NPD6928	Phase 2
0.6124	Remote Similarity	NPD6882	Approved
0.6124	Remote Similarity	NPD8297	Approved
0.6111	Remote Similarity	NPD6412	Phase 2
0.6102	Remote Similarity	NPD8034	Phase 2
0.6102	Remote Similarity	NPD8035	Phase 2
0.6075	Remote Similarity	NPD3181	Approved
0.6061	Remote Similarity	NPD6009	Approved
0.6055	Remote Similarity	NPD6117	Approved
0.6038	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD1810	Approved
0.6019	Remote Similarity	NPD1811	Approved
0.6016	Remote Similarity	NPD6373	Approved
0.6016	Remote Similarity	NPD6372	Approved
0.6016	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD8307	Discontinued
0.5984	Remote Similarity	NPD8140	Approved
0.5971	Remote Similarity	NPD6033	Approved
0.5969	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD3703	Phase 2
0.5923	Remote Similarity	NPD6649	Approved
0.5923	Remote Similarity	NPD6650	Approved
0.592	Remote Similarity	NPD8301	Approved
0.592	Remote Similarity	NPD8300	Approved
0.5906	Remote Similarity	NPD5739	Approved
0.5906	Remote Similarity	NPD7128	Approved
0.5906	Remote Similarity	NPD6402	Approved
0.5906	Remote Similarity	NPD6675	Approved
0.5905	Remote Similarity	NPD898	Approved
0.5905	Remote Similarity	NPD896	Approved
0.5905	Remote Similarity	NPD897	Approved
0.5899	Remote Similarity	NPD8074	Phase 3
0.5891	Remote Similarity	NPD8306	Approved
0.5891	Remote Similarity	NPD8305	Approved
0.5882	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7503	Approved
0.5872	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD7902	Approved
0.5846	Remote Similarity	NPD8087	Discontinued
0.5839	Remote Similarity	NPD8080	Discontinued
0.5833	Remote Similarity	NPD4632	Approved
0.5814	Remote Similarity	NPD6881	Approved
0.5814	Remote Similarity	NPD7320	Approved
0.5814	Remote Similarity	NPD6899	Approved
0.5802	Remote Similarity	NPD8130	Phase 1
0.5794	Remote Similarity	NPD7139	Approved
0.5794	Remote Similarity	NPD7140	Approved
0.5794	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD2254	Approved
0.5741	Remote Similarity	NPD2686	Approved
0.5741	Remote Similarity	NPD2687	Approved
0.5738	Remote Similarity	NPD7748	Approved
0.5736	Remote Similarity	NPD5697	Approved
0.5736	Remote Similarity	NPD5701	Approved
0.5736	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD7102	Approved
0.5725	Remote Similarity	NPD7290	Approved
0.5725	Remote Similarity	NPD6883	Approved
0.5704	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5693	Remote Similarity	NPD8346	Approved
0.5693	Remote Similarity	NPD8345	Approved
0.5693	Remote Similarity	NPD8347	Approved
0.5683	Remote Similarity	NPD7604	Phase 2
0.5682	Remote Similarity	NPD6847	Approved
0.5682	Remote Similarity	NPD6869	Approved
0.5682	Remote Similarity	NPD6617	Approved
0.5676	Remote Similarity	NPD3702	Approved
0.5652	Remote Similarity	NPD5983	Phase 2
0.5649	Remote Similarity	NPD6013	Approved
0.5649	Remote Similarity	NPD6014	Approved
0.5649	Remote Similarity	NPD6012	Approved
0.5648	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.561	Remote Similarity	NPD7900	Approved
0.561	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD4634	Approved
0.5603	Remote Similarity	NPD6336	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data