NPASS Compound

Structure

NPC240592 OpenBabel07101718232D 42 45 0 0 1 0 0 0 0 0999 V2000 -3.2562 2.9344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3678 1.2396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7279 2.9338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0807 2.3986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3460 1.0317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7061 2.7259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4115 1.6554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 1.0827 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5130 2.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0588 2.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0151 1.7748 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 -5.0733 0.1691 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 -6.7206 0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 2 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 -0.0000 -2.0000 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 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6720 0.9781 0.0000 C 0 0 2 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 -1.5620 2.5743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9933 1.5669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6987 0.4965 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 -0.0000 -3.0000 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 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 -6.0514 -0.0388 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7210 1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 3 37 1 0 0 0 0 4 7 1 0 0 0 0 4 14 2 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 17 1 0 0 0 0 10 28 1 0 0 0 0 11 29 1 0 0 0 0 12 16 2 0 0 0 0 12 38 1 0 0 0 0 13 30 2 0 0 0 0 13 42 1 0 0 0 0 15 31 1 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 39 1 6 0 0 0 18 11 1 6 0 0 0 18 22 1 0 0 0 0 18 40 1 0 0 0 0 19 32 2 0 0 0 0 19 39 1 0 0 0 0 20 16 1 1 0 0 0 20 21 1 0 0 0 0 21 26 1 0 0 0 0 21 28 1 1 0 0 0 22 23 1 0 0 0 0 22 33 1 1 0 0 0 23 24 1 0 0 0 0 23 34 1 6 0 0 0 24 27 1 0 0 0 0 24 35 1 1 0 0 0 25 36 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 28 2 1 1 0 0 0 28 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.19
Volume:	560.59
LogP:	1.361
LogD:	0.823
LogS:	-2.357
# Rotatable Bonds:	11
TPSA:	207.74
# H-Bond Aceptor:	14
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.146
Synthetic Accessibility Score:	4.972
Fsp3:	0.536
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.167
MDCK Permeability:	9.157415479421616e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.61
Human Intestinal Absorption (HIA):	0.92
20% Bioavailability (F20%):	0.82
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	53.978912353515625%
Volume Distribution (VD):	0.376
Pgp-substrate:	26.946353912353516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.188
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	1.657
Half-life (T1/2):	0.956

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.277
Drug-inuced Liver Injury (DILI):	0.694
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.275
Maximum Recommended Daily Dose:	0.148
Skin Sensitization:	0.555
Carcinogencity:	0.806
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.728

Download Data

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

Natural Product: NPC240592

Natural Product ID:	NPC240592
*Common Name:**	6-O-P-Trans-Coumaroyl-8-O-Acetylshanzhiside Methyl Ester
IUPAC Name:	methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
Synonyms:
Standard InCHIKey:	VWZXXWQOKCWKSB-PSVLUTBBSA-N
Standard InCHI:	InChI=1S/C28H34O14/c1-13(30)42-28(2)10-17(39-19(32)9-6-14-4-7-15(31)8-5-14)20-16(25(36)37-3)12-38-26(21(20)28)41-27-24(35)23(34)22(33)18(11-29)40-27/h4-9,12,17-18,20-24,26-27,29,31,33-35H,10-11H2,1-3H3/b9-6+/t17-,18-,20+,21-,22-,23+,24-,26+,27+,28+/m1/s1
SMILES:	CC(=O)O[C@@]1(C)C[C@H]([C@@H]2C(=CO[C@H]([C@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)OC)OC(=O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500818
PubChem CID:	24096431
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
NPO5652	Barleria lupulina	Species	Acanthaceae	Eukaryota	aerial part	purchased in Vung Tau, Vietnam	2012-MAR	PMID[25611215]
NPO17110	Barleria prionitis	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784173]
NPO5652	Barleria lupulina	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5652	Barleria lupulina	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5652	Barleria lupulina	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17110	Barleria prionitis	Species	Acanthaceae	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
EC50	1
IC50	2
Others	1

Activity Type	# Activity
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	EC50	=	2.46	ug.mL-1	PMID[465111]
NPT27	Others	Unspecified		IC50	=	42.0	ug.mL-1	PMID[465111]
NPT2	Others	Unspecified		Ratio IC50/EC50	=	17.0	n.a.	PMID[465111]
NPT35	Others	n.a.		IC50	=	486.5	ug.mL-1	PMID[465112]

☑ 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 NPC240592 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	311
0.1-0.2	1089
0.2-0.3	2519
0.3-0.4	4735
0.4-0.5	9304
0.5-0.6	10298
0.6-0.7	10910
0.7-0.8	3319
0.8-0.85	135
0.85-0.9	51
0.9-0.95	14
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC117346
0.979	High Similarity	NPC96599
0.9577	High Similarity	NPC296659
0.9577	High Similarity	NPC202391
0.9521	High Similarity	NPC289021
0.9521	High Similarity	NPC158546
0.9463	High Similarity	NPC475378
0.9441	High Similarity	NPC184464
0.9441	High Similarity	NPC251062
0.9396	High Similarity	NPC475484
0.9388	High Similarity	NPC475379
0.9384	High Similarity	NPC478234
0.9384	High Similarity	NPC478236
0.9371	High Similarity	NPC186296
0.9231	High Similarity	NPC154262
0.9231	High Similarity	NPC137501
0.9231	High Similarity	NPC7518
0.9231	High Similarity	NPC159387
0.9195	High Similarity	NPC194705
0.9195	High Similarity	NPC478235
0.9133	High Similarity	NPC229354
0.9091	High Similarity	NPC220936
0.9091	High Similarity	NPC49597
0.9091	High Similarity	NPC31745
0.9085	High Similarity	NPC179914
0.9048	High Similarity	NPC119773
0.9048	High Similarity	NPC143246
0.9048	High Similarity	NPC474268
0.9048	High Similarity	NPC475539
0.898	High Similarity	NPC475528
0.8974	High Similarity	NPC109990
0.8966	High Similarity	NPC46644
0.8947	High Similarity	NPC478232
0.8933	High Similarity	NPC35097
0.8919	High Similarity	NPC473147
0.8912	High Similarity	NPC194938
0.8912	High Similarity	NPC77922
0.8912	High Similarity	NPC473281
0.8912	High Similarity	NPC63304
0.891	High Similarity	NPC476011
0.891	High Similarity	NPC145847
0.8903	High Similarity	NPC474936
0.8903	High Similarity	NPC138993
0.8873	High Similarity	NPC322503
0.8873	High Similarity	NPC470143
0.8844	High Similarity	NPC152796
0.8844	High Similarity	NPC88754
0.8844	High Similarity	NPC237872
0.8844	High Similarity	NPC475213
0.8844	High Similarity	NPC263397
0.8844	High Similarity	NPC302286
0.8844	High Similarity	NPC116104
0.8844	High Similarity	NPC293154
0.8811	High Similarity	NPC169398
0.88	High Similarity	NPC120728
0.8792	High Similarity	NPC212808
0.875	High Similarity	NPC474620
0.875	High Similarity	NPC21956
0.8742	High Similarity	NPC130730
0.8742	High Similarity	NPC301910
0.8742	High Similarity	NPC161955
0.8733	High Similarity	NPC473149
0.8725	High Similarity	NPC210330
0.8671	High Similarity	NPC206815
0.8667	High Similarity	NPC37838
0.8662	High Similarity	NPC208676
0.8662	High Similarity	NPC130489
0.8658	High Similarity	NPC478240
0.8654	High Similarity	NPC187205
0.8636	High Similarity	NPC257847
0.863	High Similarity	NPC101686
0.863	High Similarity	NPC65262
0.863	High Similarity	NPC469364
0.8627	High Similarity	NPC478249
0.8627	High Similarity	NPC269914
0.8625	High Similarity	NPC282551
0.8609	High Similarity	NPC18789
0.8601	High Similarity	NPC254819
0.8591	High Similarity	NPC478250
0.8571	High Similarity	NPC203664
0.8562	High Similarity	NPC69367
0.8562	High Similarity	NPC472132
0.8562	High Similarity	NPC147224
0.8553	High Similarity	NPC308178
0.8535	High Similarity	NPC329997
0.8523	High Similarity	NPC296643
0.8523	High Similarity	NPC284957
0.8485	Intermediate Similarity	NPC475613
0.8481	Intermediate Similarity	NPC469384
0.8471	Intermediate Similarity	NPC478248
0.8431	Intermediate Similarity	NPC189631
0.8418	Intermediate Similarity	NPC475663
0.8418	Intermediate Similarity	NPC286919
0.8415	Intermediate Similarity	NPC470685
0.8397	Intermediate Similarity	NPC478241
0.8397	Intermediate Similarity	NPC89693
0.8397	Intermediate Similarity	NPC229548
0.8366	Intermediate Similarity	NPC470330
0.8364	Intermediate Similarity	NPC195972
0.8356	Intermediate Similarity	NPC114116
0.8345	Intermediate Similarity	NPC281798
0.8345	Intermediate Similarity	NPC478255
0.8345	Intermediate Similarity	NPC475824
0.8322	Intermediate Similarity	NPC106677
0.8311	Intermediate Similarity	NPC471345
0.8303	Intermediate Similarity	NPC254071
0.8303	Intermediate Similarity	NPC149502
0.8303	Intermediate Similarity	NPC222665
0.8303	Intermediate Similarity	NPC271755
0.8302	Intermediate Similarity	NPC226759
0.8302	Intermediate Similarity	NPC104275
0.8302	Intermediate Similarity	NPC49173
0.8302	Intermediate Similarity	NPC4747
0.8301	Intermediate Similarity	NPC473867
0.8291	Intermediate Similarity	NPC156624
0.8291	Intermediate Similarity	NPC172920
0.8276	Intermediate Similarity	NPC17567
0.8261	Intermediate Similarity	NPC477627
0.8258	Intermediate Similarity	NPC478242
0.8252	Intermediate Similarity	NPC267733
0.8252	Intermediate Similarity	NPC276047
0.825	Intermediate Similarity	NPC76211
0.8239	Intermediate Similarity	NPC145287
0.8239	Intermediate Similarity	NPC10945
0.8221	Intermediate Similarity	NPC180586
0.8219	Intermediate Similarity	NPC46137
0.8219	Intermediate Similarity	NPC235294
0.8217	Intermediate Similarity	NPC469456
0.8207	Intermediate Similarity	NPC469549
0.8205	Intermediate Similarity	NPC179128
0.8205	Intermediate Similarity	NPC87630
0.8205	Intermediate Similarity	NPC116292
0.8205	Intermediate Similarity	NPC267469
0.8199	Intermediate Similarity	NPC478265
0.8194	Intermediate Similarity	NPC173150
0.8194	Intermediate Similarity	NPC45224
0.8194	Intermediate Similarity	NPC471882
0.8194	Intermediate Similarity	NPC471881
0.8194	Intermediate Similarity	NPC23677
0.8194	Intermediate Similarity	NPC288416
0.8194	Intermediate Similarity	NPC35288
0.8194	Intermediate Similarity	NPC156692
0.8182	Intermediate Similarity	NPC291153
0.8182	Intermediate Similarity	NPC208293
0.8182	Intermediate Similarity	NPC320734
0.8176	Intermediate Similarity	NPC38699
0.8171	Intermediate Similarity	NPC469419
0.8165	Intermediate Similarity	NPC245615
0.8165	Intermediate Similarity	NPC61604
0.8165	Intermediate Similarity	NPC299706
0.8165	Intermediate Similarity	NPC115466
0.816	Intermediate Similarity	NPC161151
0.8153	Intermediate Similarity	NPC77310
0.8151	Intermediate Similarity	NPC289415
0.8151	Intermediate Similarity	NPC319995
0.8148	Intermediate Similarity	NPC117943
0.8148	Intermediate Similarity	NPC293568
0.8138	Intermediate Similarity	NPC225307
0.8133	Intermediate Similarity	NPC170718
0.8125	Intermediate Similarity	NPC471157
0.8125	Intermediate Similarity	NPC163635
0.8125	Intermediate Similarity	NPC61181
0.8125	Intermediate Similarity	NPC252114
0.8121	Intermediate Similarity	NPC233350
0.8121	Intermediate Similarity	NPC182217
0.8121	Intermediate Similarity	NPC208818
0.8121	Intermediate Similarity	NPC70680
0.811	Intermediate Similarity	NPC294722
0.8108	Intermediate Similarity	NPC477281
0.8108	Intermediate Similarity	NPC164172
0.8108	Intermediate Similarity	NPC19719
0.8108	Intermediate Similarity	NPC477280
0.8105	Intermediate Similarity	NPC204644
0.8105	Intermediate Similarity	NPC469367
0.8099	Intermediate Similarity	NPC52097
0.8095	Intermediate Similarity	NPC138777
0.8095	Intermediate Similarity	NPC225384
0.8095	Intermediate Similarity	NPC246869
0.8092	Intermediate Similarity	NPC80098
0.8089	Intermediate Similarity	NPC162569
0.8089	Intermediate Similarity	NPC12006
0.8089	Intermediate Similarity	NPC35160
0.8089	Intermediate Similarity	NPC229882
0.8089	Intermediate Similarity	NPC158635
0.8089	Intermediate Similarity	NPC182350
0.8086	Intermediate Similarity	NPC269668
0.8082	Intermediate Similarity	NPC253595
0.8079	Intermediate Similarity	NPC328273
0.8079	Intermediate Similarity	NPC321638
0.8079	Intermediate Similarity	NPC324262
0.8079	Intermediate Similarity	NPC171134
0.8079	Intermediate Similarity	NPC321184
0.8079	Intermediate Similarity	NPC62800
0.8079	Intermediate Similarity	NPC220942
0.8077	Intermediate Similarity	NPC473428
0.8069	Intermediate Similarity	NPC103533
0.8069	Intermediate Similarity	NPC175333
0.8067	Intermediate Similarity	NPC27721
0.8063	Intermediate Similarity	NPC10205
0.8061	Intermediate Similarity	NPC469459

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 NPC240592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	712
0.2-0.3	1587
0.3-0.4	2634
0.4-0.5	2237
0.5-0.6	1280
0.6-0.7	397
0.7-0.8	45
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8589	High Similarity	NPD7685	Pre-registration
0.7961	Intermediate Similarity	NPD7266	Discontinued
0.7756	Intermediate Similarity	NPD6190	Approved
0.7746	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7485	Intermediate Similarity	NPD7228	Approved
0.7468	Intermediate Similarity	NPD6653	Approved
0.7455	Intermediate Similarity	NPD8455	Phase 2
0.7442	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD37	Approved
0.7389	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6004	Phase 3
0.7389	Intermediate Similarity	NPD6002	Phase 3
0.7389	Intermediate Similarity	NPD6005	Phase 3
0.7381	Intermediate Similarity	NPD6234	Discontinued
0.7378	Intermediate Similarity	NPD4380	Phase 2
0.7365	Intermediate Similarity	NPD4966	Approved
0.7365	Intermediate Similarity	NPD4965	Approved
0.7365	Intermediate Similarity	NPD4967	Phase 2
0.7341	Intermediate Similarity	NPD7054	Approved
0.7333	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7075	Discontinued
0.732	Intermediate Similarity	NPD3764	Approved
0.731	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7074	Phase 3
0.7299	Intermediate Similarity	NPD7472	Approved
0.729	Intermediate Similarity	NPD6355	Discontinued
0.7285	Intermediate Similarity	NPD5647	Approved
0.7283	Intermediate Similarity	NPD7799	Discontinued
0.7273	Intermediate Similarity	NPD6663	Approved
0.7273	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7033	Discontinued
0.726	Intermediate Similarity	NPD9545	Approved
0.7256	Intermediate Similarity	NPD1653	Approved
0.7237	Intermediate Similarity	NPD5736	Approved
0.7232	Intermediate Similarity	NPD8313	Approved
0.7232	Intermediate Similarity	NPD8312	Approved
0.7216	Intermediate Similarity	NPD7251	Discontinued
0.7216	Intermediate Similarity	NPD6559	Discontinued
0.7212	Intermediate Similarity	NPD7458	Discontinued
0.7197	Intermediate Similarity	NPD7097	Phase 1
0.7193	Intermediate Similarity	NPD8127	Discontinued
0.7179	Intermediate Similarity	NPD230	Phase 1
0.7178	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7808	Phase 3
0.7159	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7240	Approved
0.7105	Intermediate Similarity	NPD6362	Approved
0.7091	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6801	Discontinued
0.7073	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7028	Phase 2
0.7063	Intermediate Similarity	NPD5762	Approved
0.7063	Intermediate Similarity	NPD5763	Approved
0.7055	Intermediate Similarity	NPD7236	Approved
0.7041	Intermediate Similarity	NPD5760	Phase 2
0.7041	Intermediate Similarity	NPD5761	Phase 2
0.7037	Intermediate Similarity	NPD8166	Discontinued
0.7037	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6273	Approved
0.6993	Remote Similarity	NPD3094	Phase 2
0.6987	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1091	Approved
0.6947	Remote Similarity	NPD7435	Discontinued
0.6946	Remote Similarity	NPD7239	Suspended
0.6943	Remote Similarity	NPD6233	Phase 2
0.6941	Remote Similarity	NPD7819	Suspended
0.6923	Remote Similarity	NPD8434	Phase 2
0.6923	Remote Similarity	NPD8150	Discontinued
0.6914	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8320	Phase 1
0.6911	Remote Similarity	NPD8319	Approved
0.6901	Remote Similarity	NPD6685	Approved
0.6901	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3751	Discontinued
0.6883	Remote Similarity	NPD2797	Approved
0.6882	Remote Similarity	NPD1934	Approved
0.6879	Remote Similarity	NPD3268	Approved
0.6879	Remote Similarity	NPD6798	Discontinued
0.6872	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5124	Phase 1
0.6854	Remote Similarity	NPD5844	Phase 1
0.6853	Remote Similarity	NPD7930	Approved
0.6848	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7473	Discontinued
0.6832	Remote Similarity	NPD1510	Phase 2
0.6829	Remote Similarity	NPD3750	Approved
0.6824	Remote Similarity	NPD7411	Suspended
0.681	Remote Similarity	NPD1549	Phase 2
0.681	Remote Similarity	NPD2424	Discontinued
0.6807	Remote Similarity	NPD6799	Approved
0.6804	Remote Similarity	NPD7585	Approved
0.6802	Remote Similarity	NPD5402	Approved
0.6802	Remote Similarity	NPD3817	Phase 2
0.6797	Remote Similarity	NPD1608	Approved
0.6795	Remote Similarity	NPD2861	Phase 2
0.6792	Remote Similarity	NPD4140	Approved
0.6791	Remote Similarity	NPD6534	Approved
0.6791	Remote Similarity	NPD6535	Approved
0.6789	Remote Similarity	NPD6780	Approved
0.6789	Remote Similarity	NPD6778	Approved
0.6789	Remote Similarity	NPD6777	Approved
0.6789	Remote Similarity	NPD6781	Approved
0.6789	Remote Similarity	NPD6782	Approved
0.6789	Remote Similarity	NPD6776	Approved
0.6789	Remote Similarity	NPD6779	Approved
0.6788	Remote Similarity	NPD7999	Approved
0.6786	Remote Similarity	NPD5403	Approved
0.678	Remote Similarity	NPD6166	Phase 2
0.678	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7699	Phase 2
0.6772	Remote Similarity	NPD7700	Phase 2
0.6771	Remote Similarity	NPD7497	Discontinued
0.6768	Remote Similarity	NPD1652	Phase 2
0.6766	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2533	Approved
0.6766	Remote Similarity	NPD2532	Approved
0.6766	Remote Similarity	NPD2534	Approved
0.6765	Remote Similarity	NPD6599	Discontinued
0.6761	Remote Similarity	NPD6232	Discontinued
0.6761	Remote Similarity	NPD3787	Discontinued
0.6753	Remote Similarity	NPD7583	Approved
0.6748	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5058	Phase 3
0.6744	Remote Similarity	NPD2801	Approved
0.6744	Remote Similarity	NPD1465	Phase 2
0.674	Remote Similarity	NPD6764	Approved
0.674	Remote Similarity	NPD6765	Approved
0.6737	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7874	Approved
0.6735	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3092	Approved
0.6727	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4110	Phase 3
0.6725	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3749	Approved
0.6711	Remote Similarity	NPD5126	Approved
0.6711	Remote Similarity	NPD5125	Phase 3
0.6709	Remote Similarity	NPD7095	Approved
0.6709	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5958	Discontinued
0.6701	Remote Similarity	NPD7783	Phase 2
0.6701	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.669	Remote Similarity	NPD5765	Approved
0.669	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6099	Approved
0.6687	Remote Similarity	NPD6100	Approved
0.6687	Remote Similarity	NPD2796	Approved
0.6687	Remote Similarity	NPD2935	Discontinued
0.6685	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8151	Discontinued
0.6684	Remote Similarity	NPD7696	Phase 3
0.6684	Remote Similarity	NPD7697	Approved
0.6684	Remote Similarity	NPD7698	Approved
0.6684	Remote Similarity	NPD7680	Approved
0.6667	Remote Similarity	NPD7584	Approved
0.6667	Remote Similarity	NPD6674	Discontinued
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD6912	Phase 3
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7870	Phase 2
0.6649	Remote Similarity	NPD7871	Phase 2
0.6648	Remote Similarity	NPD5494	Approved
0.6647	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5735	Approved
0.6644	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2067	Discontinued
0.6633	Remote Similarity	NPD7701	Phase 2
0.6632	Remote Similarity	NPD6823	Phase 2
0.663	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2799	Discontinued
0.6625	Remote Similarity	NPD4062	Phase 3
0.6624	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6085	Phase 2
0.6624	Remote Similarity	NPD2798	Approved
0.6621	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD7801	Approved
0.6609	Remote Similarity	NPD5353	Approved
0.6604	Remote Similarity	NPD3027	Phase 3
0.6603	Remote Similarity	NPD1876	Approved
0.6601	Remote Similarity	NPD3019	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