NPASS Compound

Structure

CID14849 OpenBabel06191715342D 33 35 0 0 1 0 0 0 0 0999 V2000 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 5.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 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 -5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 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 -5.1962 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 4 1 0 0 0 0 2 10 2 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 7 14 1 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 23 1 0 0 0 0 10 17 1 0 0 0 0 11 22 1 0 0 0 0 12 8 1 1 0 0 0 12 27 1 0 0 0 0 13 6 1 6 0 0 0 13 19 1 0 0 0 0 13 24 1 0 0 0 0 14 28 2 0 0 0 0 14 29 1 0 0 0 0 15 16 2 0 0 0 0 15 18 1 0 0 0 0 15 27 1 0 0 0 0 16 23 1 0 0 0 0 16 25 1 0 0 0 0 17 24 1 0 0 0 0 17 30 2 0 0 0 0 18 26 2 0 0 0 0 18 31 1 0 0 0 0 19 32 2 0 0 0 0 19 33 1 0 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	459.19
Volume:	434.797
LogP:	-1.855
LogD:	-0.493
LogS:	-4.598
# Rotatable Bonds:	10
TPSA:	203.5
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	3.747
Fsp3:	0.35
Lipinski Rule-of-5:	Rejected
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:	-7.073
MDCK Permeability:	1.7026741261361167e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.508
20% Bioavailability (F20%):	0.121
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.128
Plasma Protein Binding (PPB):	67.2890396118164%
Volume Distribution (VD):	0.229
Pgp-substrate:	43.52312088012695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.036
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.03
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	3.506
Half-life (T1/2):	0.94

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.223
Skin Sensitization:	0.16
Carcinogencity:	0.261
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.467

Download Data

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

Natural Product: NPC14849

Natural Product ID:	NPC14849
*Common Name:**	Levomefolic Acid
IUPAC Name:	(2S)-2-[[4-[[(6S)-2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl]methylamino]benzoyl]amino]pentanedioic acid
Synonyms:	Bodyfolin; Levomefolic Acid; LMSR; Metafolin; Nutrifolin
Standard InCHIKey:	ZNOVTXRBGFNYRX-STQMWFEESA-N
Standard InCHI:	InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12-,13-/m0/s1
SMILES:	OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)NC[C@H]1CNc2c(N1C)c(O)nc(=N)[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1231574
PubChem CID:	444412
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000109] Pteridines and derivatives [CHEMONTID:0000110] Pterins and derivatives [CHEMONTID:0003042] Tetrahydropteroic acids and derivatives [CHEMONTID:0002618] Tetrahydrofolic acids and derivatives [CHEMONTID:0002954] Tetrahydrofolic acids

*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

☑ 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
Ki	2
Others	1

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT304	Individual Protein	Canalicular multispecific organic anion transporter 1	Rattus norvegicus	Km	=	126000.0	nM	PMID[524121]
NPT304	Individual Protein	Canalicular multispecific organic anion transporter 1	Rattus norvegicus	Ki	=	121000.0	nM	PMID[524121]
NPT750	Individual Protein	Solute carrier organic anion transporter family member 1A3	Rattus norvegicus	Ki	=	1200.0	nM	PMID[524122]

☑ 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 NPC14849 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	448
0.1-0.2	5588
0.2-0.3	13842
0.3-0.4	16075
0.4-0.5	3541
0.5-0.6	2842
0.6-0.7	335
0.7-0.8	16
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC328611
0.9812	High Similarity	NPC182057
0.9812	High Similarity	NPC131450
0.9812	High Similarity	NPC147298
0.9625	High Similarity	NPC248862
0.7897	Intermediate Similarity	NPC147983
0.7897	Intermediate Similarity	NPC177996
0.787	Intermediate Similarity	NPC84317
0.7818	Intermediate Similarity	NPC478039
0.7778	Intermediate Similarity	NPC154478
0.7468	Intermediate Similarity	NPC322433
0.7398	Intermediate Similarity	NPC471155
0.736	Intermediate Similarity	NPC270241
0.7347	Intermediate Similarity	NPC225400
0.731	Intermediate Similarity	NPC470786
0.731	Intermediate Similarity	NPC472538
0.7247	Intermediate Similarity	NPC138293
0.7247	Intermediate Similarity	NPC189116
0.7247	Intermediate Similarity	NPC113056
0.7216	Intermediate Similarity	NPC106118
0.715	Intermediate Similarity	NPC470787
0.715	Intermediate Similarity	NPC472540
0.715	Intermediate Similarity	NPC472539
0.7113	Intermediate Similarity	NPC472542
0.7113	Intermediate Similarity	NPC472541
0.7015	Intermediate Similarity	NPC285192
0.7	Intermediate Similarity	NPC2823
0.6985	Remote Similarity	NPC295548
0.6977	Remote Similarity	NPC314186
0.6959	Remote Similarity	NPC472241
0.6939	Remote Similarity	NPC471199
0.6936	Remote Similarity	NPC472242
0.6932	Remote Similarity	NPC314223
0.6923	Remote Similarity	NPC287358
0.6923	Remote Similarity	NPC471130
0.6909	Remote Similarity	NPC472245
0.6901	Remote Similarity	NPC43477
0.6895	Remote Similarity	NPC471742
0.6893	Remote Similarity	NPC117032
0.6891	Remote Similarity	NPC471196
0.6891	Remote Similarity	NPC471195
0.6875	Remote Similarity	NPC248601
0.6865	Remote Similarity	NPC292265
0.6851	Remote Similarity	NPC68650
0.6851	Remote Similarity	NPC27904
0.6848	Remote Similarity	NPC150863
0.6842	Remote Similarity	NPC472243
0.6842	Remote Similarity	NPC242933
0.6827	Remote Similarity	NPC471197
0.6813	Remote Similarity	NPC88970
0.6794	Remote Similarity	NPC471198
0.6771	Remote Similarity	NPC307396
0.6768	Remote Similarity	NPC472244
0.6768	Remote Similarity	NPC470343
0.6754	Remote Similarity	NPC470317
0.6746	Remote Similarity	NPC162417
0.6746	Remote Similarity	NPC316104
0.6707	Remote Similarity	NPC194562
0.6707	Remote Similarity	NPC280807
0.6707	Remote Similarity	NPC314431
0.6705	Remote Similarity	NPC471164
0.6701	Remote Similarity	NPC473815
0.6686	Remote Similarity	NPC83214
0.6685	Remote Similarity	NPC473329
0.6684	Remote Similarity	NPC276430
0.6667	Remote Similarity	NPC314098
0.6667	Remote Similarity	NPC475607
0.6649	Remote Similarity	NPC475685
0.6648	Remote Similarity	NPC311658
0.6648	Remote Similarity	NPC24617
0.6633	Remote Similarity	NPC313293
0.6632	Remote Similarity	NPC474081
0.6628	Remote Similarity	NPC132636
0.6614	Remote Similarity	NPC475594
0.6613	Remote Similarity	NPC182131
0.6612	Remote Similarity	NPC114806
0.6608	Remote Similarity	NPC300299
0.6596	Remote Similarity	NPC355
0.6596	Remote Similarity	NPC318183
0.6578	Remote Similarity	NPC66490
0.6575	Remote Similarity	NPC295021
0.6557	Remote Similarity	NPC104345
0.6555	Remote Similarity	NPC6865
0.6555	Remote Similarity	NPC471194
0.6555	Remote Similarity	NPC153980
0.6555	Remote Similarity	NPC471193
0.6552	Remote Similarity	NPC471944
0.655	Remote Similarity	NPC253476
0.6543	Remote Similarity	NPC220698
0.6534	Remote Similarity	NPC478040
0.6532	Remote Similarity	NPC122553
0.6526	Remote Similarity	NPC470548
0.6522	Remote Similarity	NPC36495
0.6517	Remote Similarity	NPC324445
0.651	Remote Similarity	NPC475761
0.651	Remote Similarity	NPC475094
0.651	Remote Similarity	NPC474041
0.6509	Remote Similarity	NPC244425
0.6509	Remote Similarity	NPC15384
0.6507	Remote Similarity	NPC72956
0.6505	Remote Similarity	NPC471191
0.648	Remote Similarity	NPC254798
0.6477	Remote Similarity	NPC91179
0.6457	Remote Similarity	NPC207554
0.6456	Remote Similarity	NPC473376
0.6445	Remote Similarity	NPC471741
0.6444	Remote Similarity	NPC300596
0.6444	Remote Similarity	NPC237649
0.6433	Remote Similarity	NPC207428
0.6432	Remote Similarity	NPC276085
0.6432	Remote Similarity	NPC92803
0.6429	Remote Similarity	NPC235194
0.6414	Remote Similarity	NPC316405
0.6402	Remote Similarity	NPC226143
0.64	Remote Similarity	NPC315224
0.64	Remote Similarity	NPC319645
0.6393	Remote Similarity	NPC469903
0.6389	Remote Similarity	NPC13470
0.6387	Remote Similarity	NPC285622
0.6385	Remote Similarity	NPC471192
0.6378	Remote Similarity	NPC222029
0.6378	Remote Similarity	NPC228835
0.6378	Remote Similarity	NPC1390
0.6378	Remote Similarity	NPC123241
0.6378	Remote Similarity	NPC62104
0.6374	Remote Similarity	NPC473341
0.6369	Remote Similarity	NPC205946
0.6368	Remote Similarity	NPC472118
0.6364	Remote Similarity	NPC27833
0.6364	Remote Similarity	NPC35510
0.6364	Remote Similarity	NPC253667
0.6349	Remote Similarity	NPC279527
0.6349	Remote Similarity	NPC214960
0.6345	Remote Similarity	NPC133003
0.6344	Remote Similarity	NPC469902
0.6339	Remote Similarity	NPC285381
0.6337	Remote Similarity	NPC476689
0.6337	Remote Similarity	NPC476687
0.6337	Remote Similarity	NPC476685
0.6332	Remote Similarity	NPC18890
0.6324	Remote Similarity	NPC94167
0.6324	Remote Similarity	NPC172937
0.6321	Remote Similarity	NPC471743
0.6319	Remote Similarity	NPC239357
0.6313	Remote Similarity	NPC314114
0.6313	Remote Similarity	NPC136002
0.6307	Remote Similarity	NPC469560
0.6302	Remote Similarity	NPC177261
0.6296	Remote Similarity	NPC471124
0.6294	Remote Similarity	NPC285923
0.6294	Remote Similarity	NPC97584
0.6283	Remote Similarity	NPC274198
0.6283	Remote Similarity	NPC198254
0.6277	Remote Similarity	NPC293458
0.6275	Remote Similarity	NPC316282
0.6272	Remote Similarity	NPC474926
0.6267	Remote Similarity	NPC272174
0.6265	Remote Similarity	NPC279385
0.6265	Remote Similarity	NPC179605
0.6257	Remote Similarity	NPC469901
0.6257	Remote Similarity	NPC471122
0.6257	Remote Similarity	NPC111428
0.6256	Remote Similarity	NPC11126
0.625	Remote Similarity	NPC473002
0.6243	Remote Similarity	NPC5719
0.6243	Remote Similarity	NPC22883
0.6243	Remote Similarity	NPC217804
0.6243	Remote Similarity	NPC210377
0.6237	Remote Similarity	NPC196243
0.6237	Remote Similarity	NPC63370
0.6237	Remote Similarity	NPC36836
0.6236	Remote Similarity	NPC470301
0.6235	Remote Similarity	NPC57051
0.6235	Remote Similarity	NPC477937
0.623	Remote Similarity	NPC473000
0.623	Remote Similarity	NPC469904
0.623	Remote Similarity	NPC470971
0.623	Remote Similarity	NPC300443
0.6229	Remote Similarity	NPC314835
0.6228	Remote Similarity	NPC103292
0.6228	Remote Similarity	NPC71684
0.6225	Remote Similarity	NPC472293
0.6223	Remote Similarity	NPC309531
0.6223	Remote Similarity	NPC472102
0.6223	Remote Similarity	NPC474058
0.6222	Remote Similarity	NPC130797
0.6218	Remote Similarity	NPC242269
0.6216	Remote Similarity	NPC471132
0.6215	Remote Similarity	NPC54744
0.6213	Remote Similarity	NPC192533
0.6211	Remote Similarity	NPC15068
0.621	Remote Similarity	NPC478141
0.6205	Remote Similarity	NPC89987
0.6205	Remote Similarity	NPC177684
0.6205	Remote Similarity	NPC186669
0.6205	Remote Similarity	NPC291962
0.6203	Remote Similarity	NPC61013
0.6202	Remote Similarity	NPC471436
0.62	Remote Similarity	NPC17059
0.6199	Remote Similarity	NPC72473

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 NPC14849 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	625
0.2-0.3	970
0.3-0.4	1934
0.4-0.5	2678
0.5-0.6	2200
0.6-0.7	471
0.7-0.8	30
0.8-0.85	5
0.85-0.9	3
0.9-0.95	1
0.95-1	13

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4092	Approved
0.9937	High Similarity	NPD4091	Approved
0.9873	High Similarity	NPD3522	Approved
0.9812	High Similarity	NPD3998	Approved
0.9812	High Similarity	NPD3997	Approved
0.9812	High Similarity	NPD3999	Approved
0.975	High Similarity	NPD3995	Approved
0.975	High Similarity	NPD3993	Approved
0.975	High Similarity	NPD3991	Approved
0.975	High Similarity	NPD3992	Approved
0.975	High Similarity	NPD3994	Approved
0.975	High Similarity	NPD3996	Approved
0.9691	High Similarity	NPD3990	Phase 3
0.963	High Similarity	NPD3989	Phase 3
0.8297	Intermediate Similarity	NPD5856	Discontinued
0.8214	Intermediate Similarity	NPD4564	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD4565	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD3968	Approved
0.7897	Intermediate Similarity	NPD3353	Approved
0.7853	Intermediate Similarity	NPD3410	Approved
0.7853	Intermediate Similarity	NPD3411	Phase 2
0.7824	Intermediate Similarity	NPD4517	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD3967	Approved
0.7772	Intermediate Similarity	NPD5042	Phase 1
0.7765	Intermediate Similarity	NPD7014	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5748	Phase 2
0.7627	Intermediate Similarity	NPD5727	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1781	Discontinued
0.7468	Intermediate Similarity	NPD9540	Approved
0.741	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7855	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD9541	Approved
0.7342	Intermediate Similarity	NPD9539	Approved
0.7341	Intermediate Similarity	NPD2603	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4087	Phase 2
0.7314	Intermediate Similarity	NPD212	Discontinued
0.7283	Intermediate Similarity	NPD3518	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6613	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4464	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5024	Approved
0.7209	Intermediate Similarity	NPD979	Approved
0.7202	Intermediate Similarity	NPD3625	Discontinued
0.7193	Intermediate Similarity	NPD3519	Discontinued
0.7167	Intermediate Similarity	NPD2966	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1124	Approved
0.7152	Intermediate Similarity	NPD1123	Approved
0.715	Intermediate Similarity	NPD5510	Approved
0.7097	Intermediate Similarity	NPD5445	Approved
0.7091	Intermediate Similarity	NPD3137	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1619	Phase 3
0.7062	Intermediate Similarity	NPD951	Approved
0.7045	Intermediate Similarity	NPD2360	Approved
0.7037	Intermediate Similarity	NPD6557	Phase 2
0.7033	Intermediate Similarity	NPD6752	Phase 1
0.7033	Intermediate Similarity	NPD6753	Phase 1
0.7027	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4077	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5941	Approved
0.7011	Intermediate Similarity	NPD5942	Approved
0.6995	Remote Similarity	NPD7569	Approved
0.6995	Remote Similarity	NPD7570	Approved
0.6984	Remote Similarity	NPD5923	Phase 1
0.6982	Remote Similarity	NPD7142	Discontinued
0.6982	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3917	Approved
0.6961	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3918	Approved
0.6959	Remote Similarity	NPD6768	Approved
0.6952	Remote Similarity	NPD5775	Approved
0.6952	Remote Similarity	NPD5774	Approved
0.694	Remote Similarity	NPD2037	Approved
0.6937	Remote Similarity	NPD1079	Discontinued
0.6923	Remote Similarity	NPD4214	Discontinued
0.6915	Remote Similarity	NPD4329	Approved
0.6915	Remote Similarity	NPD4330	Approved
0.6912	Remote Similarity	NPD3915	Approved
0.6905	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4412	Phase 2
0.6893	Remote Similarity	NPD3248	Phase 1
0.6882	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3016	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5918	Discontinued
0.6872	Remote Similarity	NPD7105	Phase 1
0.6865	Remote Similarity	NPD2432	Approved
0.6865	Remote Similarity	NPD2431	Approved
0.6862	Remote Similarity	NPD3782	Discontinued
0.6857	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2454	Approved
0.6848	Remote Similarity	NPD2455	Approved
0.6847	Remote Similarity	NPD7232	Discontinued
0.6839	Remote Similarity	NPD6017	Discontinued
0.6832	Remote Similarity	NPD6260	Discontinued
0.6821	Remote Similarity	NPD2820	Phase 3
0.6818	Remote Similarity	NPD4432	Discontinued
0.6818	Remote Similarity	NPD4161	Discontinued
0.6809	Remote Similarity	NPD3792	Approved
0.68	Remote Similarity	NPD7817	Phase 1
0.6784	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2365	Approved
0.6761	Remote Similarity	NPD1802	Approved
0.6761	Remote Similarity	NPD1801	Approved
0.6759	Remote Similarity	NPD7552	Discontinued
0.6758	Remote Similarity	NPD7600	Phase 2
0.6747	Remote Similarity	NPD4549	Discontinued
0.6743	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD3606	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6901	Phase 3
0.6723	Remote Similarity	NPD5423	Phase 2
0.672	Remote Similarity	NPD5840	Discontinued
0.6707	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2010	Phase 3
0.6703	Remote Similarity	NPD33	Approved
0.6703	Remote Similarity	NPD4393	Approved
0.6702	Remote Similarity	NPD3471	Approved
0.6702	Remote Similarity	NPD3470	Approved
0.6701	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1967	Approved
0.6686	Remote Similarity	NPD1968	Approved
0.6685	Remote Similarity	NPD3790	Phase 2
0.6684	Remote Similarity	NPD8240	Discontinued
0.6683	Remote Similarity	NPD6487	Approved
0.6683	Remote Similarity	NPD4882	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6486	Approved
0.6667	Remote Similarity	NPD1070	Approved
0.6667	Remote Similarity	NPD2506	Approved
0.6667	Remote Similarity	NPD1069	Approved
0.6667	Remote Similarity	NPD2413	Phase 2
0.6667	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3468	Approved
0.663	Remote Similarity	NPD7072	Phase 2
0.663	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4682	Phase 2
0.6629	Remote Similarity	NPD4942	Approved
0.6629	Remote Similarity	NPD1664	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5581	Approved
0.6627	Remote Similarity	NPD1919	Approved
0.6627	Remote Similarity	NPD1920	Approved
0.6623	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD2723	Phase 3
0.6614	Remote Similarity	NPD5466	Approved
0.6612	Remote Similarity	NPD7599	Phase 2
0.661	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2331	Discontinued
0.6608	Remote Similarity	NPD3908	Approved
0.6607	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3776	Discontinued
0.6595	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD2356	Phase 1
0.6591	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD941	Approved
0.6587	Remote Similarity	NPD5993	Phase 1
0.6578	Remote Similarity	NPD2404	Discontinued
0.6577	Remote Similarity	NPD7677	Discontinued
0.6575	Remote Similarity	NPD5086	Approved
0.6573	Remote Similarity	NPD6088	Approved
0.657	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7205	Discontinued
0.6561	Remote Similarity	NPD7854	Phase 2
0.6557	Remote Similarity	NPD8630	Approved
0.6556	Remote Similarity	NPD5982	Phase 2
0.6553	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7727	Phase 2
0.655	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7528	Approved
0.6536	Remote Similarity	NPD4185	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6358	Phase 2
0.6526	Remote Similarity	NPD2359	Approved
0.6522	Remote Similarity	NPD2427	Approved
0.652	Remote Similarity	NPD3773	Approved
0.652	Remote Similarity	NPD7724	Phase 2
0.652	Remote Similarity	NPD3775	Approved
0.652	Remote Similarity	NPD3774	Approved
0.6519	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD1524	Phase 1
0.6515	Remote Similarity	NPD5077	Approved
0.6515	Remote Similarity	NPD5504	Discontinued
0.6515	Remote Similarity	NPD5076	Approved
0.6514	Remote Similarity	NPD8076	Discontinued
0.6513	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.651	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4677	Discontinued
0.6503	Remote Similarity	NPD6395	Phase 2
0.6503	Remote Similarity	NPD7091	Discontinued
0.6503	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6210	Phase 3
0.6492	Remote Similarity	NPD2361	Approved
0.6491	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4311	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