NPASS Compound

Structure

NPC475035 OpenBabel07101719152D 23 23 0 0 1 0 0 0 0 0999 V2000 -2.3660 1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1340 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 1.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 3.3660 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 9 1 0 0 0 0 4 16 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 10 3 1 1 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 6 0 0 0 12 13 1 0 0 0 0 12 18 1 1 0 0 0 13 15 1 0 0 0 0 13 19 1 6 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 1 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.17
Volume:	330.358
LogP:	1.094
LogD:	0.11
LogS:	-1.203
# Rotatable Bonds:	7
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.501
Synthetic Accessibility Score:	4.766
Fsp3:	0.688
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.554
MDCK Permeability:	0.00011892797192558646
Pgp-inhibitor:	0.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.604
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.204

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.21
Plasma Protein Binding (PPB):	65.67668914794922%
Volume Distribution (VD):	0.33
Pgp-substrate:	32.442115783691406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.839
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.182
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.259
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	1.418
Half-life (T1/2):	0.909

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.063
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.111
Carcinogencity:	0.009
Eye Corrosion:	0.005
Eye Irritation:	0.136
Respiratory Toxicity:	0.082

Download Data

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

Natural Product: NPC475035

Natural Product ID:	NPC475035
*Common Name:**	Rac-Menthiafolic Acid 6-O-Beta-D-Quinovopyranoside
IUPAC Name:	(2E)-2,6-dimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyocta-2,7-dienoic acid
Synonyms:
Standard InCHIKey:	GGHLYRUPOWRANQ-SFUNJQCVSA-N
Standard InCHI:	InChI=1S/C16H26O7/c1-5-16(4,8-6-7-9(2)14(20)21)23-15-13(19)12(18)11(17)10(3)22-15/h5,7,10-13,15,17-19H,1,6,8H2,2-4H3,(H,20,21)/b9-7+/t10-,11-,12+,13-,15+,16?/m1/s1
SMILES:	CC1C(C(C(C(O1)OC(C)(CCC=C(C)C(=O)O)C=C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL493441
PubChem CID:	23902356
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000215] Sugar acids and derivatives

*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
NPO3615	Acacia concinna	Species	Fabaceae	Eukaryota	fruits	myanmar	n.a.	PMID[11141109]
NPO3615	Acacia concinna	Species	Fabaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	>	100.0	ug ml-1	PMID[500920]

☑ 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 NPC475035 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	170
0.1-0.2	1508
0.2-0.3	5470
0.3-0.4	13091
0.4-0.5	12287
0.5-0.6	7206
0.6-0.7	2529
0.7-0.8	371
0.8-0.85	40
0.85-0.9	18
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC475037
0.9383	High Similarity	NPC475034
0.9259	High Similarity	NPC266718
0.8974	High Similarity	NPC229655
0.8736	High Similarity	NPC477749
0.8734	High Similarity	NPC326661
0.8706	High Similarity	NPC118077
0.8706	High Similarity	NPC475186
0.869	High Similarity	NPC470124
0.8675	High Similarity	NPC473315
0.8675	High Similarity	NPC142111
0.8659	High Similarity	NPC469469
0.8636	High Similarity	NPC472196
0.8636	High Similarity	NPC472195
0.8636	High Similarity	NPC238090
0.8571	High Similarity	NPC473308
0.8554	High Similarity	NPC251026
0.8539	High Similarity	NPC159698
0.8506	High Similarity	NPC477748
0.8409	Intermediate Similarity	NPC118078
0.8409	Intermediate Similarity	NPC202886
0.8391	Intermediate Similarity	NPC470137
0.8372	Intermediate Similarity	NPC208473
0.8313	Intermediate Similarity	NPC127295
0.8313	Intermediate Similarity	NPC163362
0.8295	Intermediate Similarity	NPC285588
0.8256	Intermediate Similarity	NPC471494
0.8222	Intermediate Similarity	NPC61201
0.8202	Intermediate Similarity	NPC6414
0.8202	Intermediate Similarity	NPC327253
0.8202	Intermediate Similarity	NPC303451
0.8161	Intermediate Similarity	NPC311163
0.8132	Intermediate Similarity	NPC294293
0.8111	Intermediate Similarity	NPC110072
0.8105	Intermediate Similarity	NPC13171
0.8105	Intermediate Similarity	NPC195510
0.8043	Intermediate Similarity	NPC170204
0.8025	Intermediate Similarity	NPC472174
0.8023	Intermediate Similarity	NPC44261
0.8022	Intermediate Similarity	NPC320089
0.8022	Intermediate Similarity	NPC320552
0.8	Intermediate Similarity	NPC473311
0.7979	Intermediate Similarity	NPC169468
0.7979	Intermediate Similarity	NPC61630
0.7979	Intermediate Similarity	NPC307517
0.7979	Intermediate Similarity	NPC81483
0.7978	Intermediate Similarity	NPC137368
0.7976	Intermediate Similarity	NPC321728
0.7959	Intermediate Similarity	NPC254538
0.7959	Intermediate Similarity	NPC474285
0.7957	Intermediate Similarity	NPC306041
0.7952	Intermediate Similarity	NPC475711
0.7935	Intermediate Similarity	NPC2003
0.7935	Intermediate Similarity	NPC25701
0.7917	Intermediate Similarity	NPC201191
0.7912	Intermediate Similarity	NPC9447
0.7895	Intermediate Similarity	NPC255677
0.7895	Intermediate Similarity	NPC306344
0.7895	Intermediate Similarity	NPC22149
0.7857	Intermediate Similarity	NPC477314
0.7857	Intermediate Similarity	NPC248775
0.7849	Intermediate Similarity	NPC469543
0.7841	Intermediate Similarity	NPC477746
0.7841	Intermediate Similarity	NPC477747
0.7812	Intermediate Similarity	NPC198992
0.7812	Intermediate Similarity	NPC298255
0.7812	Intermediate Similarity	NPC28304
0.7805	Intermediate Similarity	NPC472173
0.7802	Intermediate Similarity	NPC117596
0.7791	Intermediate Similarity	NPC280367
0.7789	Intermediate Similarity	NPC203627
0.7765	Intermediate Similarity	NPC180725
0.7765	Intermediate Similarity	NPC470149
0.7765	Intermediate Similarity	NPC470148
0.7755	Intermediate Similarity	NPC86095
0.7742	Intermediate Similarity	NPC475927
0.7742	Intermediate Similarity	NPC256368
0.7742	Intermediate Similarity	NPC475832
0.7738	Intermediate Similarity	NPC474026
0.7738	Intermediate Similarity	NPC110813
0.7717	Intermediate Similarity	NPC472199
0.7717	Intermediate Similarity	NPC472197
0.7717	Intermediate Similarity	NPC472126
0.7717	Intermediate Similarity	NPC472124
0.7717	Intermediate Similarity	NPC472125
0.7717	Intermediate Similarity	NPC469410
0.7684	Intermediate Similarity	NPC474194
0.7683	Intermediate Similarity	NPC132938
0.7677	Intermediate Similarity	NPC239961
0.7674	Intermediate Similarity	NPC133226
0.7674	Intermediate Similarity	NPC470147
0.7667	Intermediate Similarity	NPC313658
0.7667	Intermediate Similarity	NPC125142
0.7667	Intermediate Similarity	NPC316138
0.766	Intermediate Similarity	NPC101051
0.7653	Intermediate Similarity	NPC267869
0.7653	Intermediate Similarity	NPC118761
0.7653	Intermediate Similarity	NPC284929
0.7653	Intermediate Similarity	NPC234304
0.7653	Intermediate Similarity	NPC197541
0.7647	Intermediate Similarity	NPC133377
0.764	Intermediate Similarity	NPC470658
0.7629	Intermediate Similarity	NPC57586
0.7629	Intermediate Similarity	NPC471637
0.7629	Intermediate Similarity	NPC154132
0.7629	Intermediate Similarity	NPC475655
0.7629	Intermediate Similarity	NPC475157
0.7629	Intermediate Similarity	NPC2313
0.7614	Intermediate Similarity	NPC263087
0.7614	Intermediate Similarity	NPC2379
0.7614	Intermediate Similarity	NPC27314
0.7614	Intermediate Similarity	NPC31019
0.7614	Intermediate Similarity	NPC106912
0.7609	Intermediate Similarity	NPC471569
0.7609	Intermediate Similarity	NPC3952
0.7609	Intermediate Similarity	NPC307699
0.7604	Intermediate Similarity	NPC40182
0.7604	Intermediate Similarity	NPC472015
0.7604	Intermediate Similarity	NPC198422
0.759	Intermediate Similarity	NPC315843
0.759	Intermediate Similarity	NPC107654
0.7579	Intermediate Similarity	NPC54731
0.7579	Intermediate Similarity	NPC241911
0.7564	Intermediate Similarity	NPC31496
0.7553	Intermediate Similarity	NPC472198
0.7551	Intermediate Similarity	NPC250545
0.7551	Intermediate Similarity	NPC261117
0.7551	Intermediate Similarity	NPC222062
0.7551	Intermediate Similarity	NPC310804
0.7528	Intermediate Similarity	NPC78673
0.7528	Intermediate Similarity	NPC288471
0.7528	Intermediate Similarity	NPC186155
0.7528	Intermediate Similarity	NPC160517
0.7526	Intermediate Similarity	NPC130792
0.75	Intermediate Similarity	NPC11383
0.75	Intermediate Similarity	NPC475046
0.75	Intermediate Similarity	NPC315070
0.75	Intermediate Similarity	NPC310450
0.75	Intermediate Similarity	NPC96597
0.75	Intermediate Similarity	NPC91197
0.75	Intermediate Similarity	NPC40812
0.75	Intermediate Similarity	NPC125551
0.75	Intermediate Similarity	NPC474959
0.75	Intermediate Similarity	NPC309503
0.75	Intermediate Similarity	NPC155319
0.75	Intermediate Similarity	NPC472290
0.75	Intermediate Similarity	NPC239547
0.75	Intermediate Similarity	NPC82251
0.75	Intermediate Similarity	NPC133450
0.7475	Intermediate Similarity	NPC197736
0.7473	Intermediate Similarity	NPC45409
0.747	Intermediate Similarity	NPC477303
0.747	Intermediate Similarity	NPC477311
0.7468	Intermediate Similarity	NPC19769
0.7449	Intermediate Similarity	NPC20673
0.7449	Intermediate Similarity	NPC219038
0.7447	Intermediate Similarity	NPC471483
0.7442	Intermediate Similarity	NPC279532
0.7423	Intermediate Similarity	NPC187268
0.7423	Intermediate Similarity	NPC187761
0.7423	Intermediate Similarity	NPC83895
0.7419	Intermediate Similarity	NPC270908
0.7419	Intermediate Similarity	NPC470573
0.7419	Intermediate Similarity	NPC65665
0.7419	Intermediate Similarity	NPC177668
0.7419	Intermediate Similarity	NPC231710
0.7419	Intermediate Similarity	NPC216826
0.7419	Intermediate Similarity	NPC473448
0.7419	Intermediate Similarity	NPC120021
0.7416	Intermediate Similarity	NPC315559
0.7416	Intermediate Similarity	NPC161045
0.7416	Intermediate Similarity	NPC284472
0.7416	Intermediate Similarity	NPC286770
0.7416	Intermediate Similarity	NPC229799
0.74	Intermediate Similarity	NPC474917
0.7396	Intermediate Similarity	NPC173329
0.7396	Intermediate Similarity	NPC472995
0.7396	Intermediate Similarity	NPC143446
0.7396	Intermediate Similarity	NPC288350
0.7391	Intermediate Similarity	NPC471755
0.7391	Intermediate Similarity	NPC471756
0.7391	Intermediate Similarity	NPC248312
0.7386	Intermediate Similarity	NPC473339
0.7386	Intermediate Similarity	NPC21693
0.7386	Intermediate Similarity	NPC471552
0.7386	Intermediate Similarity	NPC236649
0.7381	Intermediate Similarity	NPC477308
0.7381	Intermediate Similarity	NPC477315
0.7381	Intermediate Similarity	NPC477305
0.7381	Intermediate Similarity	NPC477316
0.7381	Intermediate Similarity	NPC477304
0.7381	Intermediate Similarity	NPC477312
0.7381	Intermediate Similarity	NPC477309
0.7381	Intermediate Similarity	NPC477313
0.7375	Intermediate Similarity	NPC201356
0.7374	Intermediate Similarity	NPC471599
0.7374	Intermediate Similarity	NPC121423
0.7368	Intermediate Similarity	NPC71589
0.7363	Intermediate Similarity	NPC61527
0.7363	Intermediate Similarity	NPC47937

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 NPC475035 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1861
0.2-0.3	4079
0.3-0.4	2143
0.4-0.5	664
0.5-0.6	224
0.6-0.7	26
0.7-0.8	5
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
0.7789	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6698	Approved
0.7419	Intermediate Similarity	NPD46	Approved
0.7419	Intermediate Similarity	NPD7838	Discovery
0.7353	Intermediate Similarity	NPD6686	Approved
0.71	Intermediate Similarity	NPD5344	Discontinued
0.6957	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6633	Remote Similarity	NPD7983	Approved
0.6607	Remote Similarity	NPD7328	Approved
0.6607	Remote Similarity	NPD7327	Approved
0.6579	Remote Similarity	NPD8513	Phase 3
0.6579	Remote Similarity	NPD8516	Approved
0.6579	Remote Similarity	NPD8515	Approved
0.6579	Remote Similarity	NPD8517	Approved
0.6549	Remote Similarity	NPD7516	Approved
0.6491	Remote Similarity	NPD8294	Approved
0.6491	Remote Similarity	NPD8377	Approved
0.6489	Remote Similarity	NPD6110	Phase 1
0.6466	Remote Similarity	NPD7642	Approved
0.6466	Remote Similarity	NPD7830	Approved
0.6466	Remote Similarity	NPD7829	Approved
0.6435	Remote Similarity	NPD8380	Approved
0.6435	Remote Similarity	NPD8378	Approved
0.6435	Remote Similarity	NPD8033	Approved
0.6435	Remote Similarity	NPD8296	Approved
0.6435	Remote Similarity	NPD8335	Approved
0.6435	Remote Similarity	NPD8379	Approved
0.6429	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6371	Approved
0.6408	Remote Similarity	NPD4225	Approved
0.6364	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7507	Approved
0.6316	Remote Similarity	NPD7641	Discontinued
0.6296	Remote Similarity	NPD6412	Phase 2
0.6296	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4249	Approved
0.6224	Remote Similarity	NPD4250	Approved
0.6224	Remote Similarity	NPD4251	Approved
0.6214	Remote Similarity	NPD7839	Suspended
0.6198	Remote Similarity	NPD7319	Approved
0.617	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD1407	Approved
0.6154	Remote Similarity	NPD8444	Approved
0.6092	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD8451	Approved
0.6038	Remote Similarity	NPD7640	Approved
0.6038	Remote Similarity	NPD7639	Approved
0.6033	Remote Similarity	NPD8448	Approved
0.6033	Remote Similarity	NPD8074	Phase 3
0.602	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4821	Approved
0.6	Remote Similarity	NPD4822	Approved
0.6	Remote Similarity	NPD8341	Approved
0.6	Remote Similarity	NPD8342	Approved
0.6	Remote Similarity	NPD8299	Approved
0.6	Remote Similarity	NPD8340	Approved
0.6	Remote Similarity	NPD4819	Approved
0.6	Remote Similarity	NPD4820	Approved
0.598	Remote Similarity	NPD7637	Suspended
0.5979	Remote Similarity	NPD7154	Phase 3
0.5965	Remote Similarity	NPD8133	Approved
0.5957	Remote Similarity	NPD4271	Approved
0.5957	Remote Similarity	NPD4268	Approved
0.5952	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7638	Approved
0.5922	Remote Similarity	NPD5778	Approved
0.5922	Remote Similarity	NPD5779	Approved
0.5909	Remote Similarity	NPD4211	Phase 1
0.5904	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD6109	Phase 1
0.5893	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD8392	Approved
0.5887	Remote Similarity	NPD8390	Approved
0.5887	Remote Similarity	NPD8391	Approved
0.5882	Remote Similarity	NPD5785	Approved
0.5876	Remote Similarity	NPD5209	Approved
0.5859	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD905	Approved
0.5823	Remote Similarity	NPD904	Phase 3
0.5812	Remote Similarity	NPD7115	Discovery
0.581	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD8328	Phase 3
0.5761	Remote Similarity	NPD4732	Discontinued
0.5755	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.575	Remote Similarity	NPD2269	Approved
0.5739	Remote Similarity	NPD969	Suspended
0.5739	Remote Similarity	NPD6053	Discontinued
0.573	Remote Similarity	NPD896	Approved
0.573	Remote Similarity	NPD898	Approved
0.573	Remote Similarity	NPD897	Approved
0.5726	Remote Similarity	NPD7736	Approved
0.5714	Remote Similarity	NPD9119	Approved
0.5714	Remote Similarity	NPD69	Approved
0.5714	Remote Similarity	NPD5282	Discontinued
0.5714	Remote Similarity	NPD7266	Discontinued
0.5702	Remote Similarity	NPD6421	Discontinued
0.5702	Remote Similarity	NPD6370	Approved
0.57	Remote Similarity	NPD5363	Approved
0.5698	Remote Similarity	NPD368	Approved
0.5691	Remote Similarity	NPD8273	Phase 1
0.5684	Remote Similarity	NPD4756	Discovery
0.5679	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD888	Phase 3
0.5679	Remote Similarity	NPD895	Approved
0.5679	Remote Similarity	NPD894	Approved
0.5679	Remote Similarity	NPD889	Approved
0.5679	Remote Similarity	NPD893	Approved
0.5679	Remote Similarity	NPD891	Phase 3
0.5679	Remote Similarity	NPD887	Approved
0.5679	Remote Similarity	NPD892	Phase 3
0.5678	Remote Similarity	NPD7500	Approved
0.5678	Remote Similarity	NPD7505	Discontinued
0.5678	Remote Similarity	NPD6009	Approved
0.5657	Remote Similarity	NPD5362	Discontinued
0.5652	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD1695	Approved
0.5625	Remote Similarity	NPD6927	Phase 3
0.5625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.561	Remote Similarity	NPD7492	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