NPASS Compound

Structure

NPC145847 OpenBabel07101718332D 47 51 0 0 1 0 0 0 0 0999 V2000 -3.8581 0.2399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -3.5491 1.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 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 -5.1962 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 -0.8660 1.5000 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 -2.0000 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 8 2 0 0 0 0 2 15 1 0 0 0 0 3 9 2 0 0 0 0 3 15 1 0 0 0 0 4 6 1 0 0 0 0 4 16 2 0 0 0 0 5 7 2 0 0 0 0 5 16 1 0 0 0 0 6 17 2 0 0 0 0 7 17 1 0 0 0 0 8 20 1 0 0 0 0 9 24 1 0 0 0 0 10 15 2 0 0 0 0 10 22 1 0 0 0 0 11 21 1 0 0 0 0 12 19 2 0 0 0 0 12 44 1 0 0 0 0 13 43 1 0 0 0 0 14 1 1 6 0 0 0 14 21 1 0 0 0 0 14 25 1 0 0 0 0 16 30 1 0 0 0 0 17 33 1 0 0 0 0 18 11 1 6 0 0 0 18 19 1 0 0 0 0 18 25 1 0 0 0 0 19 29 1 0 0 0 0 20 22 2 0 0 0 0 20 34 1 0 0 0 0 21 35 1 1 0 0 0 22 36 1 0 0 0 0 23 13 1 6 0 0 0 23 26 1 0 0 0 0 23 45 1 0 0 0 0 24 37 2 0 0 0 0 24 43 1 0 0 0 0 25 31 1 0 0 0 0 26 27 1 0 0 0 0 26 38 1 0 0 0 0 27 28 1 0 0 0 0 27 39 1 0 0 0 0 28 32 1 0 0 0 0 28 46 1 0 0 0 0 29 40 2 0 0 0 0 29 41 1 0 0 0 0 30 42 2 0 0 0 0 30 46 1 0 0 0 0 31 44 1 0 0 0 0 31 47 1 0 0 0 0 32 45 1 0 0 0 0 32 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	658.19
Volume:	622.098
LogP:	2.639
LogD:	1.398
LogS:	-2.992
# Rotatable Bonds:	11
TPSA:	238.97
# H-Bond Aceptor:	15
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.113
Synthetic Accessibility Score:	4.959
Fsp3:	0.406
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.446
MDCK Permeability:	4.622393680620007e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.082
Human Intestinal Absorption (HIA):	0.894
20% Bioavailability (F20%):	0.738
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.105
Plasma Protein Binding (PPB):	96.50829315185547%
Volume Distribution (VD):	0.355
Pgp-substrate:	6.9174275398254395%

ADMET: Metabolism

CYP1A2-inhibitor:	0.11
CYP1A2-substrate:	0.019
CYP2C19-inhibitor:	0.125
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.461
CYP2C9-substrate:	0.186
CYP2D6-inhibitor:	0.095
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.181
CYP3A4-substrate:	0.083

ADMET: Excretion

Clearance (CL):	3.977
Half-life (T1/2):	0.966

ADMET: Toxicity

hERG Blockers:	0.199
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.19
Maximum Recommended Daily Dose:	0.052
Skin Sensitization:	0.63
Carcinogencity:	0.688
Eye Corrosion:	0.003
Eye Irritation:	0.068
Respiratory Toxicity:	0.758

Download Data

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

Natural Product: NPC145847

Natural Product ID:	NPC145847
*Common Name:**	2'-O-P-Hydroxybenzoyl-6'-O-Trans-Caffeoyl-8-Epiloganic Acid
IUPAC Name:	(1S,4aS,6S,7S,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxyoxan-2-yl]oxy-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
Synonyms:
Standard InCHIKey:	LCVJKCLBUJNLAY-ZLTHKTTISA-N
Standard InCHI:	InChI=1S/C32H34O15/c1-14-21(35)11-18-19(29(40)41)12-44-31(25(14)18)47-32-28(46-30(42)16-4-6-17(33)7-5-16)27(39)26(38)23(45-32)13-43-24(37)9-3-15-2-8-20(34)22(36)10-15/h2-10,12,14,18,21,23,25-28,31-36,38-39H,11,13H2,1H3,(H,40,41)/b9-3+/t14-,18-,21+,23-,25-,26-,27+,28-,31+,32+/m1/s1
SMILES:	O=C(/C=C/c1ccc(c(c1)O)O)OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@H](C)[C@H](C3)O)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508253
PubChem CID:	11365823
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
NPO6184	Vitex altissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620243]
NPO6184	Vitex altissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6184	Vitex altissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	31900.0	nM	PMID[457093]
NPT1	Others	Radical scavenging activity		IC50	=	11400.0	nM	PMID[457093]

☑ 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 NPC145847 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	342
0.1-0.2	1282
0.2-0.3	2780
0.3-0.4	5839
0.4-0.5	10357
0.5-0.6	7879
0.6-0.7	8699
0.7-0.8	5058
0.8-0.85	387
0.85-0.9	63
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC109990
0.9739	High Similarity	NPC187205
0.9684	High Similarity	NPC21956
0.9355	High Similarity	NPC475484
0.9299	High Similarity	NPC179914
0.9221	High Similarity	NPC289021
0.9221	High Similarity	NPC158546
0.9125	High Similarity	NPC476011
0.9119	High Similarity	NPC138993
0.9	High Similarity	NPC474936
0.8968	High Similarity	NPC478236
0.8968	High Similarity	NPC96599
0.8968	High Similarity	NPC478234
0.8957	High Similarity	NPC130730
0.8957	High Similarity	NPC301910
0.891	High Similarity	NPC117346
0.891	High Similarity	NPC240592
0.891	High Similarity	NPC69367
0.8889	High Similarity	NPC202391
0.8889	High Similarity	NPC296659
0.8875	High Similarity	NPC226759
0.8841	High Similarity	NPC282551
0.8802	High Similarity	NPC316539
0.8797	High Similarity	NPC194705
0.8797	High Similarity	NPC478235
0.8773	High Similarity	NPC206815
0.8766	High Similarity	NPC77922
0.8766	High Similarity	NPC473281
0.8758	High Similarity	NPC49173
0.8742	High Similarity	NPC229354
0.8742	High Similarity	NPC157898
0.8734	High Similarity	NPC140151
0.8734	High Similarity	NPC475379
0.8696	High Similarity	NPC471405
0.8688	High Similarity	NPC194095
0.8688	High Similarity	NPC191046
0.8688	High Similarity	NPC327032
0.8679	High Similarity	NPC203664
0.8654	High Similarity	NPC473867
0.865	High Similarity	NPC208676
0.865	High Similarity	NPC478265
0.865	High Similarity	NPC130489
0.8645	High Similarity	NPC184464
0.8645	High Similarity	NPC251062
0.8642	High Similarity	NPC4747
0.8642	High Similarity	NPC472860
0.8642	High Similarity	NPC133984
0.8642	High Similarity	NPC104275
0.8639	High Similarity	NPC171706
0.8636	High Similarity	NPC296643
0.8634	High Similarity	NPC172920
0.8634	High Similarity	NPC10205
0.8634	High Similarity	NPC156624
0.8631	High Similarity	NPC470685
0.8625	High Similarity	NPC257847
0.8616	High Similarity	NPC478249
0.8616	High Similarity	NPC269914
0.8608	High Similarity	NPC92117
0.8606	High Similarity	NPC100420
0.8599	High Similarity	NPC473149
0.8589	High Similarity	NPC469384
0.8581	High Similarity	NPC478250
0.8581	High Similarity	NPC186296
0.858	High Similarity	NPC475299
0.8571	High Similarity	NPC472128
0.8571	High Similarity	NPC472127
0.8571	High Similarity	NPC478232
0.8563	High Similarity	NPC208818
0.8562	High Similarity	NPC267091
0.8562	High Similarity	NPC134905
0.8562	High Similarity	NPC478268
0.8562	High Similarity	NPC36130
0.8554	High Similarity	NPC180586
0.8554	High Similarity	NPC475738
0.8553	High Similarity	NPC35097
0.8545	High Similarity	NPC246024
0.8544	High Similarity	NPC120728
0.8544	High Similarity	NPC28776
0.8544	High Similarity	NPC248257
0.8544	High Similarity	NPC120621
0.8544	High Similarity	NPC473138
0.8544	High Similarity	NPC23677
0.8537	High Similarity	NPC239966
0.8537	High Similarity	NPC203020
0.8528	High Similarity	NPC286919
0.8528	High Similarity	NPC475663
0.8519	High Similarity	NPC203757
0.8519	High Similarity	NPC131532
0.8512	High Similarity	NPC266545
0.8512	High Similarity	NPC202428
0.8509	High Similarity	NPC61152
0.8509	High Similarity	NPC205037
0.8509	High Similarity	NPC245615
0.8509	High Similarity	NPC299706
0.8509	High Similarity	NPC137813
0.8509	High Similarity	NPC115466
0.8509	High Similarity	NPC16024
0.8509	High Similarity	NPC3746
0.8509	High Similarity	NPC61604
0.8509	High Similarity	NPC44260
0.8506	High Similarity	NPC299855
0.8506	High Similarity	NPC96194
0.85	High Similarity	NPC243891
0.8497	Intermediate Similarity	NPC302583
0.8497	Intermediate Similarity	NPC84789
0.8497	Intermediate Similarity	NPC310252
0.8497	Intermediate Similarity	NPC473205
0.8497	Intermediate Similarity	NPC100558
0.8497	Intermediate Similarity	NPC473776
0.8491	Intermediate Similarity	NPC161955
0.8491	Intermediate Similarity	NPC111785
0.8488	Intermediate Similarity	NPC198902
0.8481	Intermediate Similarity	NPC18789
0.848	Intermediate Similarity	NPC67629
0.848	Intermediate Similarity	NPC79736
0.8476	Intermediate Similarity	NPC160780
0.8476	Intermediate Similarity	NPC289811
0.8466	Intermediate Similarity	NPC475378
0.8466	Intermediate Similarity	NPC478248
0.8462	Intermediate Similarity	NPC293154
0.8457	Intermediate Similarity	NPC189704
0.8452	Intermediate Similarity	NPC476385
0.8452	Intermediate Similarity	NPC298847
0.8452	Intermediate Similarity	NPC7518
0.8452	Intermediate Similarity	NPC134405
0.8452	Intermediate Similarity	NPC177362
0.8452	Intermediate Similarity	NPC154262
0.8452	Intermediate Similarity	NPC159387
0.8452	Intermediate Similarity	NPC47471
0.8452	Intermediate Similarity	NPC137501
0.8452	Intermediate Similarity	NPC476377
0.8447	Intermediate Similarity	NPC106818
0.8442	Intermediate Similarity	NPC89105
0.8442	Intermediate Similarity	NPC81515
0.8442	Intermediate Similarity	NPC64141
0.8442	Intermediate Similarity	NPC68092
0.8442	Intermediate Similarity	NPC476383
0.8442	Intermediate Similarity	NPC472350
0.8442	Intermediate Similarity	NPC197316
0.8439	Intermediate Similarity	NPC188217
0.8438	Intermediate Similarity	NPC147224
0.8434	Intermediate Similarity	NPC14030
0.8434	Intermediate Similarity	NPC33298
0.8434	Intermediate Similarity	NPC148273
0.8434	Intermediate Similarity	NPC285108
0.8434	Intermediate Similarity	NPC291957
0.8431	Intermediate Similarity	NPC471345
0.843	Intermediate Similarity	NPC469418
0.843	Intermediate Similarity	NPC260300
0.843	Intermediate Similarity	NPC267549
0.843	Intermediate Similarity	NPC80360
0.8428	Intermediate Similarity	NPC308178
0.8424	Intermediate Similarity	NPC289346
0.8421	Intermediate Similarity	NPC469354
0.8415	Intermediate Similarity	NPC172419
0.8415	Intermediate Similarity	NPC1913
0.8415	Intermediate Similarity	NPC238419
0.8409	Intermediate Similarity	NPC475121
0.8409	Intermediate Similarity	NPC476067
0.8408	Intermediate Similarity	NPC300894
0.8408	Intermediate Similarity	NPC296954
0.8408	Intermediate Similarity	NPC141455
0.8408	Intermediate Similarity	NPC196063
0.8405	Intermediate Similarity	NPC38699
0.8402	Intermediate Similarity	NPC658
0.8402	Intermediate Similarity	NPC197708
0.8397	Intermediate Similarity	NPC222433
0.8397	Intermediate Similarity	NPC265648
0.8395	Intermediate Similarity	NPC478241
0.8395	Intermediate Similarity	NPC89693
0.8395	Intermediate Similarity	NPC87403
0.8395	Intermediate Similarity	NPC44730
0.8395	Intermediate Similarity	NPC229548
0.8393	Intermediate Similarity	NPC469458
0.8393	Intermediate Similarity	NPC88176
0.8393	Intermediate Similarity	NPC149002
0.8393	Intermediate Similarity	NPC469419
0.8393	Intermediate Similarity	NPC469396
0.8393	Intermediate Similarity	NPC200726
0.8393	Intermediate Similarity	NPC469459
0.8387	Intermediate Similarity	NPC475530
0.8387	Intermediate Similarity	NPC473799
0.8385	Intermediate Similarity	NPC474620
0.8383	Intermediate Similarity	NPC470898
0.8383	Intermediate Similarity	NPC100425
0.8382	Intermediate Similarity	NPC195114
0.8377	Intermediate Similarity	NPC78363
0.8377	Intermediate Similarity	NPC260425
0.8375	Intermediate Similarity	NPC478242
0.8375	Intermediate Similarity	NPC75945
0.8375	Intermediate Similarity	NPC98809
0.8375	Intermediate Similarity	NPC476394
0.8373	Intermediate Similarity	NPC472859
0.8373	Intermediate Similarity	NPC25389
0.8373	Intermediate Similarity	NPC311803
0.8372	Intermediate Similarity	NPC469397
0.8366	Intermediate Similarity	NPC123988
0.8366	Intermediate Similarity	NPC476870
0.8364	Intermediate Similarity	NPC104222
0.8364	Intermediate Similarity	NPC74319

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 NPC145847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	774
0.2-0.3	1621
0.3-0.4	2614
0.4-0.5	2247
0.5-0.6	1173
0.6-0.7	363
0.7-0.8	67
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9264	High Similarity	NPD7685	Pre-registration
0.8442	Intermediate Similarity	NPD7266	Discontinued
0.8276	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7054	Approved
0.814	Intermediate Similarity	NPD7074	Phase 3
0.814	Intermediate Similarity	NPD7472	Approved
0.8129	Intermediate Similarity	NPD3818	Discontinued
0.8046	Intermediate Similarity	NPD7251	Discontinued
0.8024	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6797	Phase 2
0.7976	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7228	Approved
0.7901	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6190	Approved
0.7836	Intermediate Similarity	NPD7199	Phase 2
0.7771	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6234	Discontinued
0.7716	Intermediate Similarity	NPD4628	Phase 3
0.7684	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD230	Phase 1
0.7654	Intermediate Similarity	NPD8313	Approved
0.7654	Intermediate Similarity	NPD8312	Approved
0.765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD37	Approved
0.7633	Intermediate Similarity	NPD1934	Approved
0.763	Intermediate Similarity	NPD8127	Discontinued
0.7619	Intermediate Similarity	NPD4380	Phase 2
0.7602	Intermediate Similarity	NPD4967	Phase 2
0.7602	Intermediate Similarity	NPD4965	Approved
0.7602	Intermediate Similarity	NPD4966	Approved
0.76	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6166	Phase 2
0.76	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD8455	Phase 2
0.7588	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5844	Phase 1
0.7542	Intermediate Similarity	NPD6559	Discontinued
0.7514	Intermediate Similarity	NPD7799	Discontinued
0.75	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD8166	Discontinued
0.7485	Intermediate Similarity	NPD6273	Approved
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7457	Intermediate Similarity	NPD7075	Discontinued
0.7456	Intermediate Similarity	NPD7458	Discontinued
0.7444	Intermediate Similarity	NPD7240	Approved
0.7442	Intermediate Similarity	NPD3817	Phase 2
0.7384	Intermediate Similarity	NPD7819	Suspended
0.7384	Intermediate Similarity	NPD2801	Approved
0.736	Intermediate Similarity	NPD7473	Discontinued
0.7337	Intermediate Similarity	NPD8150	Discontinued
0.7321	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7028	Phase 2
0.7299	Intermediate Similarity	NPD3882	Suspended
0.7288	Intermediate Similarity	NPD6232	Discontinued
0.7283	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5494	Approved
0.7262	Intermediate Similarity	NPD1511	Approved
0.725	Intermediate Similarity	NPD3764	Approved
0.7241	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6801	Discontinued
0.7216	Intermediate Similarity	NPD8320	Phase 1
0.7216	Intermediate Similarity	NPD8319	Approved
0.7215	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7236	Approved
0.719	Intermediate Similarity	NPD9545	Approved
0.7178	Intermediate Similarity	NPD6653	Approved
0.7176	Intermediate Similarity	NPD1512	Approved
0.7165	Intermediate Similarity	NPD7680	Approved
0.7165	Intermediate Similarity	NPD7435	Discontinued
0.7157	Intermediate Similarity	NPD8151	Discontinued
0.7151	Intermediate Similarity	NPD8434	Phase 2
0.7151	Intermediate Similarity	NPD3455	Phase 2
0.715	Intermediate Similarity	NPD7930	Approved
0.7143	Intermediate Similarity	NPD5402	Approved
0.7135	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6355	Discontinued
0.7099	Intermediate Similarity	NPD6663	Approved
0.7093	Intermediate Similarity	NPD7239	Suspended
0.7092	Intermediate Similarity	NPD7999	Approved
0.7083	Intermediate Similarity	NPD3750	Approved
0.7083	Intermediate Similarity	NPD7699	Phase 2
0.7083	Intermediate Similarity	NPD7700	Phase 2
0.7081	Intermediate Similarity	NPD3027	Phase 3
0.7069	Intermediate Similarity	NPD6385	Approved
0.7069	Intermediate Similarity	NPD6386	Approved
0.7069	Intermediate Similarity	NPD7411	Suspended
0.7066	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9494	Approved
0.7063	Intermediate Similarity	NPD5736	Approved
0.7055	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2935	Discontinued
0.7035	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7874	Approved
0.7035	Intermediate Similarity	NPD5403	Approved
0.7024	Intermediate Similarity	NPD6674	Discontinued
0.7017	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6535	Approved
0.7016	Intermediate Similarity	NPD6534	Approved
0.701	Intermediate Similarity	NPD6780	Approved
0.701	Intermediate Similarity	NPD6782	Approved
0.701	Intermediate Similarity	NPD6781	Approved
0.701	Intermediate Similarity	NPD6777	Approved
0.701	Intermediate Similarity	NPD6779	Approved
0.701	Intermediate Similarity	NPD6776	Approved
0.701	Intermediate Similarity	NPD6778	Approved
0.7006	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD5762	Approved
0.7006	Intermediate Similarity	NPD7768	Phase 2
0.7	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7783	Phase 2
0.6995	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7497	Discontinued
0.699	Remote Similarity	NPD7697	Approved
0.699	Remote Similarity	NPD7698	Approved
0.699	Remote Similarity	NPD7696	Phase 3
0.6988	Remote Similarity	NPD1510	Phase 2
0.6988	Remote Similarity	NPD7033	Discontinued
0.6982	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4110	Phase 3
0.6964	Remote Similarity	NPD1549	Phase 2
0.6962	Remote Similarity	NPD9269	Phase 2
0.6962	Remote Similarity	NPD1608	Approved
0.6959	Remote Similarity	NPD6799	Approved
0.6954	Remote Similarity	NPD7871	Phase 2
0.6954	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7870	Phase 2
0.6952	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3620	Phase 2
0.6951	Remote Similarity	NPD1613	Approved
0.6951	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD943	Approved
0.6949	Remote Similarity	NPD5353	Approved
0.694	Remote Similarity	NPD3751	Discontinued
0.6935	Remote Similarity	NPD7585	Approved
0.6935	Remote Similarity	NPD7701	Phase 2
0.6919	Remote Similarity	NPD5401	Approved
0.6919	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7801	Approved
0.6914	Remote Similarity	NPD6599	Discontinued
0.6909	Remote Similarity	NPD1933	Approved
0.6905	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6004	Phase 3
0.6905	Remote Similarity	NPD6005	Phase 3
0.6905	Remote Similarity	NPD6002	Phase 3
0.6893	Remote Similarity	NPD5760	Phase 2
0.6893	Remote Similarity	NPD5761	Phase 2
0.6884	Remote Similarity	NPD7583	Approved
0.6882	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6213	Phase 3
0.6875	Remote Similarity	NPD6212	Phase 3
0.6875	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD5242	Approved
0.6853	Remote Similarity	NPD6823	Phase 2
0.6852	Remote Similarity	NPD2861	Phase 2
0.6851	Remote Similarity	NPD6959	Discontinued
0.6845	Remote Similarity	NPD2796	Approved
0.6829	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7097	Phase 1
0.6821	Remote Similarity	NPD2533	Approved
0.6821	Remote Similarity	NPD2534	Approved
0.6821	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2532	Approved
0.6821	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3787	Discontinued
0.68	Remote Similarity	NPD7584	Approved
0.6791	Remote Similarity	NPD7039	Approved
0.6791	Remote Similarity	NPD6764	Approved
0.6791	Remote Similarity	NPD7038	Approved
0.6791	Remote Similarity	NPD6765	Approved
0.679	Remote Similarity	NPD2798	Approved
0.679	Remote Similarity	NPD5647	Approved
0.6788	Remote Similarity	NPD6233	Phase 2
0.6786	Remote Similarity	NPD3748	Approved
0.6784	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3749	Approved
0.6772	Remote Similarity	NPD17	Approved
0.677	Remote Similarity	NPD1876	Approved
0.6761	Remote Similarity	NPD3226	Approved
0.676	Remote Similarity	NPD5977	Approved
0.676	Remote Similarity	NPD5978	Approved
0.6747	Remote Similarity	NPD1240	Approved
0.6747	Remote Similarity	NPD4140	Approved
0.6746	Remote Similarity	NPD2438	Suspended
0.674	Remote Similarity	NPD919	Approved
0.6728	Remote Similarity	NPD3094	Phase 2
0.6728	Remote Similarity	NPD2797	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