NPASS Compound

Structure

NPC203664 OpenBabel07101719252D 41 44 0 0 1 0 0 0 0 0999 V2000 5.7197 -0.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9777 3.2386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3304 3.7738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6468 2.4954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6394 4.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6905 2.0796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 1.7399 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 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9995 3.0306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3378 1.5443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3596 1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 4.3090 0.0000 C 0 0 2 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 3.9703 5.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 1 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 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 1 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 2.3230 0.9968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0069 0.8012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2793 6.4190 0.0000 O 0 0 0 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 1.7321 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0506 0.3854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 5.2601 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 36 1 0 0 0 0 2 37 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 15 1 0 0 0 0 6 19 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 28 1 0 0 0 0 10 29 1 0 0 0 0 11 14 2 0 0 0 0 11 38 1 0 0 0 0 14 25 1 0 0 0 0 15 16 2 0 0 0 0 15 30 1 0 0 0 0 16 36 1 0 0 0 0 17 21 1 0 0 0 0 17 39 1 6 0 0 0 18 10 1 6 0 0 0 18 22 1 0 0 0 0 18 40 1 0 0 0 0 19 31 2 0 0 0 0 19 39 1 0 0 0 0 20 13 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 14 1 1 0 0 0 22 23 1 0 0 0 0 22 32 1 1 0 0 0 23 24 1 0 0 0 0 23 33 1 6 0 0 0 24 27 1 0 0 0 0 24 34 1 1 0 0 0 25 35 2 0 0 0 0 25 37 1 0 0 0 0 26 38 1 0 0 0 0 26 41 1 6 0 0 0 27 40 1 0 0 0 0 27 41 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.18
Volume:	543.294
LogP:	0.735
LogD:	0.425
LogS:	-1.639
# Rotatable Bonds:	11
TPSA:	210.9
# H-Bond Aceptor:	14
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	4.889
Fsp3:	0.481
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.29
MDCK Permeability:	8.482298289891332e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.557
Human Intestinal Absorption (HIA):	0.867
20% Bioavailability (F20%):	0.125
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.269
Plasma Protein Binding (PPB):	45.038360595703125%
Volume Distribution (VD):	0.411
Pgp-substrate:	25.26434326171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.108
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.083
CYP3A4-substrate:	0.182

ADMET: Excretion

Clearance (CL):	2.828
Half-life (T1/2):	0.955

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.193
Rat Oral Acute Toxicity:	0.496
Maximum Recommended Daily Dose:	0.094
Skin Sensitization:	0.349
Carcinogencity:	0.728
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC203664

Natural Product ID:	NPC203664
*Common Name:**	E-6-O-P-Feruloyl Scandoside Methyl Ester
IUPAC Name:	methyl (1S,4aS,5R,7aS)-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:
Standard InCHIKey:	QHRICBJWYCXFDR-GZJXMKRRSA-N
Standard InCHI:	InChI=1S/C27H32O14/c1-36-16-7-12(3-5-15(16)30)4-6-19(31)39-17-8-13(9-28)20-21(17)14(25(35)37-2)11-38-26(20)41-27-24(34)23(33)22(32)18(10-29)40-27/h3-8,11,17-18,20-24,26-30,32-34H,9-10H2,1-2H3/b6-4+/t17-,18-,20-,21+,22-,23+,24-,26+,27+/m1/s1
SMILES:	COc1cc(ccc1O)/C=C/C(=O)O[C@@H]1C=C(CO)[C@@H]2[C@H]1C(=CO[C@H]2O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL592955
PubChem CID:	46225505
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO32921	hedyotis diffusa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170670]
NPO32921	hedyotis diffusa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20004577]

☑ 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	5

Activity Type	# Activity
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Inhibition	=	25.1	%	PMID[501379]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	IC50	>	100000.0	nM	PMID[501379]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Inhibition	=	23.6	%	PMID[501379]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Inhibition	=	22.9	%	PMID[501379]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Inhibition	=	23.3	%	PMID[501379]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Inhibition	=	24.7	%	PMID[501379]

☑ 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 NPC203664 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	322
0.1-0.2	1269
0.2-0.3	3168
0.3-0.4	7172
0.4-0.5	10488
0.5-0.6	5813
0.6-0.7	8519
0.7-0.8	5196
0.8-0.85	589
0.85-0.9	145
0.9-0.95	15
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC475213
0.9375	High Similarity	NPC152796
0.9342	High Similarity	NPC179914
0.9324	High Similarity	NPC69367
0.9216	High Similarity	NPC469384
0.9161	High Similarity	NPC476011
0.915	High Similarity	NPC475663
0.915	High Similarity	NPC286919
0.9133	High Similarity	NPC269914
0.9133	High Similarity	NPC478249
0.9128	High Similarity	NPC478242
0.9097	High Similarity	NPC220936
0.9097	High Similarity	NPC31745
0.9032	High Similarity	NPC474936
0.902	High Similarity	NPC475484
0.8987	High Similarity	NPC301910
0.8987	High Similarity	NPC130730
0.8966	High Similarity	NPC226005
0.8958	High Similarity	NPC157554
0.894	High Similarity	NPC147224
0.8933	High Similarity	NPC308178
0.8924	High Similarity	NPC180586
0.8919	High Similarity	NPC110063
0.8912	High Similarity	NPC296643
0.8903	High Similarity	NPC226759
0.8889	High Similarity	NPC245615
0.8889	High Similarity	NPC61604
0.8889	High Similarity	NPC299706
0.8889	High Similarity	NPC478241
0.8889	High Similarity	NPC89693
0.8889	High Similarity	NPC229548
0.8889	High Similarity	NPC115466
0.8875	High Similarity	NPC21956
0.8867	High Similarity	NPC473149
0.8859	High Similarity	NPC287615
0.8859	High Similarity	NPC83743
0.8859	High Similarity	NPC262182
0.8859	High Similarity	NPC216819
0.8851	High Similarity	NPC293154
0.8846	High Similarity	NPC76211
0.8836	High Similarity	NPC100389
0.8831	High Similarity	NPC327032
0.8831	High Similarity	NPC191046
0.8831	High Similarity	NPC194095
0.8797	High Similarity	NPC206815
0.8792	High Similarity	NPC202391
0.8792	High Similarity	NPC296659
0.8792	High Similarity	NPC297342
0.8784	High Similarity	NPC140502
0.8784	High Similarity	NPC157816
0.8776	High Similarity	NPC202700
0.8774	High Similarity	NPC38699
0.8766	High Similarity	NPC44730
0.8758	High Similarity	NPC475379
0.875	High Similarity	NPC282551
0.8733	High Similarity	NPC34587
0.8733	High Similarity	NPC100998
0.8733	High Similarity	NPC34927
0.8733	High Similarity	NPC476382
0.8733	High Similarity	NPC252292
0.8725	High Similarity	NPC478239
0.8718	High Similarity	NPC163635
0.8718	High Similarity	NPC478248
0.8718	High Similarity	NPC228357
0.8718	High Similarity	NPC471405
0.8707	High Similarity	NPC220942
0.8701	High Similarity	NPC36130
0.8701	High Similarity	NPC134905
0.8701	High Similarity	NPC478268
0.8699	High Similarity	NPC37468
0.8699	High Similarity	NPC186418
0.8693	High Similarity	NPC158635
0.8693	High Similarity	NPC229882
0.8684	High Similarity	NPC192763
0.8684	High Similarity	NPC80732
0.8684	High Similarity	NPC215095
0.8684	High Similarity	NPC3460
0.8684	High Similarity	NPC261122
0.8684	High Similarity	NPC199311
0.8684	High Similarity	NPC300262
0.8684	High Similarity	NPC201148
0.8684	High Similarity	NPC210611
0.8684	High Similarity	NPC28651
0.8679	High Similarity	NPC145847
0.8675	High Similarity	NPC476865
0.8671	High Similarity	NPC478265
0.8671	High Similarity	NPC138993
0.8667	High Similarity	NPC63304
0.8667	High Similarity	NPC473281
0.8667	High Similarity	NPC77922
0.8662	High Similarity	NPC187205
0.8662	High Similarity	NPC472860
0.8662	High Similarity	NPC133984
0.8654	High Similarity	NPC10205
0.8645	High Similarity	NPC246893
0.8645	High Similarity	NPC157898
0.8627	High Similarity	NPC96599
0.8627	High Similarity	NPC283839
0.8627	High Similarity	NPC90896
0.8627	High Similarity	NPC111785
0.8625	High Similarity	NPC109990
0.8618	High Similarity	NPC232992
0.8611	High Similarity	NPC254819
0.8609	High Similarity	NPC476864
0.8609	High Similarity	NPC476869
0.8609	High Similarity	NPC476866
0.8609	High Similarity	NPC476868
0.8608	High Similarity	NPC289811
0.8608	High Similarity	NPC160780
0.8599	High Similarity	NPC478055
0.8591	High Similarity	NPC186406
0.8581	High Similarity	NPC289438
0.8571	High Similarity	NPC470934
0.8571	High Similarity	NPC188393
0.8571	High Similarity	NPC117346
0.8571	High Similarity	NPC240592
0.8571	High Similarity	NPC205054
0.8571	High Similarity	NPC470572
0.8562	High Similarity	NPC41009
0.8562	High Similarity	NPC471883
0.8562	High Similarity	NPC23677
0.8553	High Similarity	NPC239966
0.8553	High Similarity	NPC199928
0.8553	High Similarity	NPC473867
0.8553	High Similarity	NPC203020
0.8552	High Similarity	NPC473285
0.8544	High Similarity	NPC1913
0.8543	High Similarity	NPC232228
0.8543	High Similarity	NPC476867
0.8537	High Similarity	NPC470685
0.8535	High Similarity	NPC131532
0.8526	High Similarity	NPC105827
0.8526	High Similarity	NPC137813
0.8526	High Similarity	NPC310661
0.8516	High Similarity	NPC7145
0.8516	High Similarity	NPC125823
0.8516	High Similarity	NPC85192
0.8516	High Similarity	NPC143480
0.8509	High Similarity	NPC100420
0.8506	High Similarity	NPC471062
0.8506	High Similarity	NPC106138
0.8506	High Similarity	NPC476386
0.8506	High Similarity	NPC306890
0.8506	High Similarity	NPC259347
0.8506	High Similarity	NPC94871
0.8506	High Similarity	NPC476398
0.8506	High Similarity	NPC470933
0.8506	High Similarity	NPC473427
0.8503	High Similarity	NPC476870
0.8503	High Similarity	NPC477301
0.85	High Similarity	NPC472859
0.85	High Similarity	NPC25389
0.85	High Similarity	NPC311803
0.8497	Intermediate Similarity	NPC18789
0.8493	Intermediate Similarity	NPC254398
0.8491	Intermediate Similarity	NPC469654
0.8485	Intermediate Similarity	NPC316539
0.8483	Intermediate Similarity	NPC219677
0.8481	Intermediate Similarity	NPC11411
0.8481	Intermediate Similarity	NPC478266
0.8477	Intermediate Similarity	NPC88754
0.8477	Intermediate Similarity	NPC263397
0.8477	Intermediate Similarity	NPC237872
0.8477	Intermediate Similarity	NPC302286
0.8477	Intermediate Similarity	NPC116104
0.8472	Intermediate Similarity	NPC229784
0.8472	Intermediate Similarity	NPC307110
0.8472	Intermediate Similarity	NPC477294
0.8472	Intermediate Similarity	NPC477293
0.8471	Intermediate Similarity	NPC472128
0.8471	Intermediate Similarity	NPC472127
0.8467	Intermediate Similarity	NPC472711
0.8462	Intermediate Similarity	NPC472612
0.8462	Intermediate Similarity	NPC289967
0.8462	Intermediate Similarity	NPC472611
0.8457	Intermediate Similarity	NPC472130
0.8457	Intermediate Similarity	NPC472131
0.8457	Intermediate Similarity	NPC475738
0.8452	Intermediate Similarity	NPC257970
0.8452	Intermediate Similarity	NPC476871
0.8452	Intermediate Similarity	NPC470927
0.8452	Intermediate Similarity	NPC227980
0.8447	Intermediate Similarity	NPC33298
0.8447	Intermediate Similarity	NPC285108
0.8447	Intermediate Similarity	NPC246024
0.8442	Intermediate Similarity	NPC478237
0.8438	Intermediate Similarity	NPC44507
0.8438	Intermediate Similarity	NPC166277
0.8438	Intermediate Similarity	NPC119125
0.8435	Intermediate Similarity	NPC169398
0.8435	Intermediate Similarity	NPC35731
0.8431	Intermediate Similarity	NPC474268
0.8431	Intermediate Similarity	NPC474234
0.8431	Intermediate Similarity	NPC475539
0.8431	Intermediate Similarity	NPC473147
0.8431	Intermediate Similarity	NPC143246
0.8431	Intermediate Similarity	NPC119773
0.8431	Intermediate Similarity	NPC98356
0.8428	Intermediate Similarity	NPC40920
0.8428	Intermediate Similarity	NPC104275

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 NPC203664 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	792
0.2-0.3	1767
0.3-0.4	2737
0.4-0.5	1981
0.5-0.6	1036
0.6-0.7	497
0.7-0.8	68
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8827	High Similarity	NPD7685	Pre-registration
0.8333	Intermediate Similarity	NPD7266	Discontinued
0.8269	Intermediate Similarity	NPD1653	Approved
0.8176	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7228	Approved
0.8037	Intermediate Similarity	NPD6234	Discontinued
0.8024	Intermediate Similarity	NPD3818	Discontinued
0.7976	Intermediate Similarity	NPD7054	Approved
0.795	Intermediate Similarity	NPD37	Approved
0.7929	Intermediate Similarity	NPD7472	Approved
0.7914	Intermediate Similarity	NPD4967	Phase 2
0.7914	Intermediate Similarity	NPD4966	Approved
0.7914	Intermediate Similarity	NPD4965	Approved
0.7898	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6190	Approved
0.7831	Intermediate Similarity	NPD7199	Phase 2
0.7824	Intermediate Similarity	NPD7074	Phase 3
0.7733	Intermediate Similarity	NPD7251	Discontinued
0.7697	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7808	Phase 3
0.7674	Intermediate Similarity	NPD6797	Phase 2
0.7633	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7240	Approved
0.7619	Intermediate Similarity	NPD8127	Discontinued
0.7568	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD230	Phase 1
0.7531	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD9494	Approved
0.743	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1934	Approved
0.7386	Intermediate Similarity	NPD3027	Phase 3
0.7375	Intermediate Similarity	NPD4628	Phase 3
0.7372	Intermediate Similarity	NPD6653	Approved
0.7365	Intermediate Similarity	NPD8455	Phase 2
0.7365	Intermediate Similarity	NPD2801	Approved
0.7347	Intermediate Similarity	NPD1357	Approved
0.7345	Intermediate Similarity	NPD8313	Approved
0.7345	Intermediate Similarity	NPD8312	Approved
0.733	Intermediate Similarity	NPD6559	Discontinued
0.7321	Intermediate Similarity	NPD3817	Phase 2
0.7315	Intermediate Similarity	NPD3705	Approved
0.7312	Intermediate Similarity	NPD6674	Discontinued
0.7297	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6166	Phase 2
0.7283	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3882	Suspended
0.7273	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1465	Phase 2
0.7262	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5844	Phase 1
0.7253	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7473	Discontinued
0.7234	Intermediate Similarity	NPD7680	Approved
0.7219	Intermediate Similarity	NPD5353	Approved
0.7207	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1091	Approved
0.7186	Intermediate Similarity	NPD4380	Phase 2
0.7186	Intermediate Similarity	NPD7028	Phase 2
0.7168	Intermediate Similarity	NPD6232	Discontinued
0.716	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD8166	Discontinued
0.716	Intermediate Similarity	NPD4110	Phase 3
0.7135	Intermediate Similarity	NPD7075	Discontinued
0.7134	Intermediate Similarity	NPD1613	Approved
0.7134	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7097	Phase 1
0.7095	Intermediate Similarity	NPD5536	Phase 2
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7089	Intermediate Similarity	NPD447	Suspended
0.7078	Intermediate Similarity	NPD5647	Approved
0.7055	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5494	Approved
0.7041	Intermediate Similarity	NPD6386	Approved
0.7041	Intermediate Similarity	NPD6385	Approved
0.7037	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1511	Approved
0.7025	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3620	Phase 2
0.7024	Intermediate Similarity	NPD7458	Discontinued
0.7018	Intermediate Similarity	NPD5402	Approved
0.7006	Intermediate Similarity	NPD3751	Discontinued
0.6988	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1933	Approved
0.6975	Remote Similarity	NPD5762	Approved
0.6975	Remote Similarity	NPD5763	Approved
0.6962	Remote Similarity	NPD6233	Phase 2
0.6959	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7819	Suspended
0.6957	Remote Similarity	NPD7033	Discontinued
0.6946	Remote Similarity	NPD1512	Approved
0.6933	Remote Similarity	NPD9545	Approved
0.6928	Remote Similarity	NPD4357	Discontinued
0.6923	Remote Similarity	NPD2861	Phase 2
0.6918	Remote Similarity	NPD228	Approved
0.6918	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6801	Discontinued
0.6899	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1652	Phase 2
0.6882	Remote Similarity	NPD7296	Approved
0.6879	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7435	Discontinued
0.6875	Remote Similarity	NPD3787	Discontinued
0.6875	Remote Similarity	NPD1358	Approved
0.6871	Remote Similarity	NPD6004	Phase 3
0.6871	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6002	Phase 3
0.6871	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6005	Phase 3
0.6848	Remote Similarity	NPD8434	Phase 2
0.6845	Remote Similarity	NPD6273	Approved
0.6835	Remote Similarity	NPD7095	Approved
0.6829	Remote Similarity	NPD2424	Discontinued
0.6818	Remote Similarity	NPD1608	Approved
0.6818	Remote Similarity	NPD9269	Phase 2
0.6815	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4060	Phase 1
0.681	Remote Similarity	NPD2935	Discontinued
0.6806	Remote Similarity	NPD3134	Approved
0.6805	Remote Similarity	NPD5403	Approved
0.6795	Remote Similarity	NPD2797	Approved
0.6795	Remote Similarity	NPD6362	Approved
0.6792	Remote Similarity	NPD3268	Approved
0.6792	Remote Similarity	NPD3764	Approved
0.6792	Remote Similarity	NPD6798	Discontinued
0.6788	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2532	Approved
0.6786	Remote Similarity	NPD8151	Discontinued
0.6786	Remote Similarity	NPD2534	Approved
0.6786	Remote Similarity	NPD2533	Approved
0.6784	Remote Similarity	NPD7930	Approved
0.677	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5124	Phase 1
0.6765	Remote Similarity	NPD3687	Approved
0.6765	Remote Similarity	NPD3686	Approved
0.6763	Remote Similarity	NPD2978	Approved
0.6763	Remote Similarity	NPD2977	Approved
0.6758	Remote Similarity	NPD7038	Approved
0.6758	Remote Similarity	NPD7039	Approved
0.6747	Remote Similarity	NPD3750	Approved
0.6742	Remote Similarity	NPD5242	Approved
0.6732	Remote Similarity	NPD1778	Approved
0.6731	Remote Similarity	NPD3225	Approved
0.6726	Remote Similarity	NPD6799	Approved
0.6725	Remote Similarity	NPD3455	Phase 2
0.6724	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6842	Approved
0.672	Remote Similarity	NPD6841	Approved
0.672	Remote Similarity	NPD6843	Phase 3
0.6719	Remote Similarity	NPD6779	Approved
0.6719	Remote Similarity	NPD6780	Approved
0.6719	Remote Similarity	NPD6781	Approved
0.6719	Remote Similarity	NPD6776	Approved
0.6719	Remote Similarity	NPD6782	Approved
0.6719	Remote Similarity	NPD6777	Approved
0.6719	Remote Similarity	NPD6778	Approved
0.6718	Remote Similarity	NPD7999	Approved
0.6711	Remote Similarity	NPD5283	Phase 1
0.6709	Remote Similarity	NPD5736	Approved
0.6708	Remote Similarity	NPD4140	Approved
0.6707	Remote Similarity	NPD2438	Suspended
0.6687	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5401	Approved
0.6683	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD2983	Phase 2
0.6667	Remote Similarity	NPD2982	Phase 2
0.6667	Remote Similarity	NPD7874	Approved
0.6667	Remote Similarity	NPD5058	Phase 3
0.6667	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD4340	Discontinued
0.6667	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6823	Phase 2
0.6647	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7411	Suspended
0.6647	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1510	Phase 2
0.6646	Remote Similarity	NPD6663	Approved
0.6646	Remote Similarity	NPD4062	Phase 3
0.6645	Remote Similarity	NPD422	Phase 1
0.6633	Remote Similarity	NPD7783	Phase 2
0.6633	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7549	Discontinued
0.6628	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD3226	Approved
0.6627	Remote Similarity	NPD1549	Phase 2
0.6626	Remote Similarity	NPD2492	Phase 1
0.6623	Remote Similarity	NPD7157	Approved
0.6623	Remote Similarity	NPD17	Approved
0.6615	Remote Similarity	NPD7696	Phase 3
0.6615	Remote Similarity	NPD7698	Approved
0.6615	Remote Similarity	NPD7697	Approved
0.661	Remote Similarity	NPD919	Approved
0.6606	Remote Similarity	NPD6100	Approved
0.6606	Remote Similarity	NPD6099	Approved
0.6603	Remote Similarity	NPD2981	Phase 2

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