NPASS Compound

Structure

NPC474620 OpenBabel07101718282D 39 43 0 0 1 0 0 0 0 0999 V2000 2.0953 5.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3659 0.3135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0704 -1.2688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2795 0.7202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9840 -0.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1756 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6934 -0.3820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0953 2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2614 -0.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0885 0.1324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3633 2.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2293 2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8274 -0.8820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3633 1.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3479 -1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8274 -1.8820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9613 -2.3820 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0953 -1.8820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2293 3.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2293 0.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0953 -0.8820 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5594 -0.8820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0020 0.5392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2433 -2.0823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6934 -2.3820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9613 -3.3820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2293 -2.3820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3633 4.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0953 4.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0953 1.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9613 -0.3820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2293 -0.3820 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 35 1 0 0 0 0 2 4 1 0 0 0 0 2 11 2 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 12 2 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 8 14 2 0 0 0 0 8 26 1 0 0 0 0 9 27 1 0 0 0 0 10 15 2 0 0 0 0 10 36 1 0 0 0 0 11 18 1 0 0 0 0 12 28 1 0 0 0 0 13 6 1 6 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 16 9 1 6 0 0 0 16 19 1 0 0 0 0 16 37 1 0 0 0 0 17 24 1 0 0 0 0 17 26 1 6 0 0 0 18 29 2 0 0 0 0 19 20 1 0 0 0 0 19 30 1 1 0 0 0 20 21 1 0 0 0 0 20 31 1 6 0 0 0 21 25 1 0 0 0 0 21 32 1 1 0 0 0 22 33 2 0 0 0 0 22 35 1 0 0 0 0 23 34 2 0 0 0 0 23 39 1 0 0 0 0 24 36 1 0 0 0 0 24 38 1 6 0 0 0 25 37 1 0 0 0 0 25 38 1 6 0 0 0 26 7 1 1 0 0 0 26 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.14
Volume:	506.015
LogP:	0.579
LogD:	-0.035
LogS:	-2.511
# Rotatable Bonds:	7
TPSA:	198.51
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.124
Synthetic Accessibility Score:	5.486
Fsp3:	0.423
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:	-6.081
MDCK Permeability:	6.557252345373854e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.913
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	49.70249938964844%
Volume Distribution (VD):	0.7
Pgp-substrate:	31.055801391601562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.085
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.467
CYP3A4-substrate:	0.154

ADMET: Excretion

Clearance (CL):	1.694
Half-life (T1/2):	0.895

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.119
Drug-inuced Liver Injury (DILI):	0.879
AMES Toxicity:	0.246
Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.126
Skin Sensitization:	0.087
Carcinogencity:	0.912
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.889

Download Data

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

Natural Product: NPC474620

Natural Product ID:	NPC474620
*Common Name:**	Dehydrogaertneroside
IUPAC Name:	methyl (1R,4aS,7R,7aS)-4'-(4-hydroxybenzoyl)-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
Synonyms:	Dehydrogaertneroside
Standard InCHIKey:	POWUQYYCVSQIAC-CMLHHFLRSA-N
Standard InCHI:	InChI=1S/C26H26O13/c1-35-22(33)15-10-36-24(38-25-21(32)20(31)19(30)16(9-27)37-25)17-13(15)6-7-26(17)8-14(23(34)39-26)18(29)11-2-4-12(28)5-3-11/h2-8,10,13,16-17,19-21,24-25,27-28,30-32H,9H2,1H3/t13-,16-,17-,19-,20+,21-,24-,25+,26-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2OC=C([C@@H]3[C@H]2[C@]2(C=C3)OC(=O)C(=C2)C(=O)c2ccc(cc2)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477146
PubChem CID:	44559438
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
NPO22304	Morinda morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542353]
NPO22304	Morinda morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20149652]
NPO22304	Morinda morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7775983]
NPO22304	Morinda morindoides	Species	Rubiaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT610	Others	Molecular identity unknown		IC50	>	400000.0	nM	PMID[465300]

☑ 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 NPC474620 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	318
0.1-0.2	1178
0.2-0.3	2707
0.3-0.4	5738
0.4-0.5	10248
0.5-0.6	8114
0.6-0.7	8294
0.7-0.8	5864
0.8-0.85	197
0.85-0.9	28
0.9-0.95	5
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.965	High Similarity	NPC475539
0.965	High Similarity	NPC474268
0.965	High Similarity	NPC119773
0.965	High Similarity	NPC143246
0.958	High Similarity	NPC475528
0.9375	High Similarity	NPC63304
0.9226	High Similarity	NPC180586
0.911	High Similarity	NPC473281
0.911	High Similarity	NPC77922
0.9067	High Similarity	NPC289021
0.9067	High Similarity	NPC158546
0.8961	High Similarity	NPC475663
0.8961	High Similarity	NPC286919
0.8933	High Similarity	NPC478234
0.8933	High Similarity	NPC478236
0.8926	High Similarity	NPC473149
0.8919	High Similarity	NPC210330
0.8903	High Similarity	NPC469384
0.8896	High Similarity	NPC475378
0.8859	High Similarity	NPC212808
0.8851	High Similarity	NPC296659
0.8851	High Similarity	NPC202391
0.8784	High Similarity	NPC478250
0.8767	High Similarity	NPC31745
0.8767	High Similarity	NPC220936
0.8759	High Similarity	NPC472132
0.8758	High Similarity	NPC194705
0.875	High Similarity	NPC117346
0.875	High Similarity	NPC240592
0.8684	High Similarity	NPC96599
0.8681	High Similarity	NPC114116
0.8671	High Similarity	NPC477627
0.8636	High Similarity	NPC478235
0.863	High Similarity	NPC471345
0.8621	High Similarity	NPC169398
0.8618	High Similarity	NPC189631
0.8609	High Similarity	NPC473147
0.8609	High Similarity	NPC291153
0.8581	High Similarity	NPC229354
0.8562	High Similarity	NPC161955
0.8533	High Similarity	NPC293154
0.8526	High Similarity	NPC478232
0.8509	High Similarity	NPC294722
0.8487	Intermediate Similarity	NPC473867
0.8481	Intermediate Similarity	NPC187205
0.8477	Intermediate Similarity	NPC251062
0.8477	Intermediate Similarity	NPC184464
0.8462	Intermediate Similarity	NPC257847
0.8457	Intermediate Similarity	NPC469419
0.8447	Intermediate Similarity	NPC109990
0.8446	Intermediate Similarity	NPC101686
0.8446	Intermediate Similarity	NPC65262
0.8446	Intermediate Similarity	NPC469364
0.8438	Intermediate Similarity	NPC293568
0.8438	Intermediate Similarity	NPC117943
0.8428	Intermediate Similarity	NPC76211
0.8414	Intermediate Similarity	NPC254819
0.8414	Intermediate Similarity	NPC281798
0.8411	Intermediate Similarity	NPC152796
0.8411	Intermediate Similarity	NPC186296
0.8411	Intermediate Similarity	NPC475213
0.8408	Intermediate Similarity	NPC472128
0.8408	Intermediate Similarity	NPC472127
0.84	Intermediate Similarity	NPC7518
0.84	Intermediate Similarity	NPC80098
0.84	Intermediate Similarity	NPC159387
0.84	Intermediate Similarity	NPC79908
0.84	Intermediate Similarity	NPC137501
0.84	Intermediate Similarity	NPC154262
0.8397	Intermediate Similarity	NPC134819
0.8395	Intermediate Similarity	NPC475979
0.8387	Intermediate Similarity	NPC35097
0.8385	Intermediate Similarity	NPC145847
0.8385	Intermediate Similarity	NPC476011
0.8375	Intermediate Similarity	NPC130489
0.8375	Intermediate Similarity	NPC138993
0.8375	Intermediate Similarity	NPC208676
0.8365	Intermediate Similarity	NPC226759
0.8365	Intermediate Similarity	NPC478226
0.8365	Intermediate Similarity	NPC43638
0.8355	Intermediate Similarity	NPC194938
0.8354	Intermediate Similarity	NPC10205
0.8354	Intermediate Similarity	NPC475484
0.8344	Intermediate Similarity	NPC157898
0.8344	Intermediate Similarity	NPC296643
0.8344	Intermediate Similarity	NPC148080
0.8344	Intermediate Similarity	NPC469623
0.8333	Intermediate Similarity	NPC475379
0.8333	Intermediate Similarity	NPC191154
0.8323	Intermediate Similarity	NPC317544
0.8313	Intermediate Similarity	NPC43761
0.8313	Intermediate Similarity	NPC73511
0.8313	Intermediate Similarity	NPC470607
0.8302	Intermediate Similarity	NPC148323
0.8302	Intermediate Similarity	NPC265480
0.8302	Intermediate Similarity	NPC283480
0.8302	Intermediate Similarity	NPC149368
0.8302	Intermediate Similarity	NPC127406
0.8302	Intermediate Similarity	NPC471405
0.8282	Intermediate Similarity	NPC72016
0.8282	Intermediate Similarity	NPC265600
0.828	Intermediate Similarity	NPC23253
0.828	Intermediate Similarity	NPC190217
0.8276	Intermediate Similarity	NPC469549
0.8272	Intermediate Similarity	NPC93215
0.8269	Intermediate Similarity	NPC267469
0.8269	Intermediate Similarity	NPC179128
0.8269	Intermediate Similarity	NPC88886
0.8269	Intermediate Similarity	NPC104172
0.8269	Intermediate Similarity	NPC87630
0.8269	Intermediate Similarity	NPC182350
0.8269	Intermediate Similarity	NPC116292
0.8269	Intermediate Similarity	NPC69367
0.8267	Intermediate Similarity	NPC49597
0.8261	Intermediate Similarity	NPC218471
0.8261	Intermediate Similarity	NPC271479
0.8261	Intermediate Similarity	NPC239818
0.8261	Intermediate Similarity	NPC474936
0.8258	Intermediate Similarity	NPC473428
0.8258	Intermediate Similarity	NPC120728
0.8255	Intermediate Similarity	NPC294470
0.825	Intermediate Similarity	NPC208651
0.825	Intermediate Similarity	NPC161749
0.825	Intermediate Similarity	NPC470606
0.825	Intermediate Similarity	NPC313163
0.825	Intermediate Similarity	NPC206641
0.825	Intermediate Similarity	NPC4747
0.825	Intermediate Similarity	NPC49173
0.825	Intermediate Similarity	NPC258035
0.825	Intermediate Similarity	NPC122809
0.825	Intermediate Similarity	NPC156457
0.825	Intermediate Similarity	NPC104275
0.825	Intermediate Similarity	NPC197896
0.8247	Intermediate Similarity	NPC474044
0.8247	Intermediate Similarity	NPC208293
0.8242	Intermediate Similarity	NPC21956
0.8239	Intermediate Similarity	NPC156624
0.8239	Intermediate Similarity	NPC95090
0.8239	Intermediate Similarity	NPC478230
0.8239	Intermediate Similarity	NPC69043
0.8239	Intermediate Similarity	NPC82190
0.8239	Intermediate Similarity	NPC27408
0.8239	Intermediate Similarity	NPC470603
0.8239	Intermediate Similarity	NPC172920
0.8239	Intermediate Similarity	NPC470604
0.8239	Intermediate Similarity	NPC192219
0.8239	Intermediate Similarity	NPC174599
0.8239	Intermediate Similarity	NPC99233
0.8239	Intermediate Similarity	NPC470605
0.8239	Intermediate Similarity	NPC472890
0.8232	Intermediate Similarity	NPC130730
0.8232	Intermediate Similarity	NPC149002
0.8232	Intermediate Similarity	NPC469396
0.8232	Intermediate Similarity	NPC469458
0.8232	Intermediate Similarity	NPC88176
0.8232	Intermediate Similarity	NPC301910
0.8232	Intermediate Similarity	NPC469459
0.8228	Intermediate Similarity	NPC137813
0.8228	Intermediate Similarity	NPC88484
0.8228	Intermediate Similarity	NPC259767
0.8221	Intermediate Similarity	NPC471286
0.8221	Intermediate Similarity	NPC121703
0.8221	Intermediate Similarity	NPC120012
0.8221	Intermediate Similarity	NPC91288
0.8219	Intermediate Similarity	NPC17567
0.8217	Intermediate Similarity	NPC477240
0.8217	Intermediate Similarity	NPC213723
0.8217	Intermediate Similarity	NPC214454
0.8217	Intermediate Similarity	NPC140151
0.8217	Intermediate Similarity	NPC106025
0.821	Intermediate Similarity	NPC270675
0.821	Intermediate Similarity	NPC129217
0.821	Intermediate Similarity	NPC303913
0.821	Intermediate Similarity	NPC85707
0.821	Intermediate Similarity	NPC159579
0.821	Intermediate Similarity	NPC216496
0.821	Intermediate Similarity	NPC224530
0.821	Intermediate Similarity	NPC259957
0.821	Intermediate Similarity	NPC69868
0.821	Intermediate Similarity	NPC195685
0.821	Intermediate Similarity	NPC210961
0.821	Intermediate Similarity	NPC101636
0.821	Intermediate Similarity	NPC48093
0.821	Intermediate Similarity	NPC472994
0.821	Intermediate Similarity	NPC477628
0.821	Intermediate Similarity	NPC477629
0.8205	Intermediate Similarity	NPC199335
0.8199	Intermediate Similarity	NPC179914
0.8199	Intermediate Similarity	NPC308265
0.8194	Intermediate Similarity	NPC470330
0.8194	Intermediate Similarity	NPC252114
0.8187	Intermediate Similarity	NPC45165
0.8187	Intermediate Similarity	NPC17521
0.8176	Intermediate Similarity	NPC106625
0.8176	Intermediate Similarity	NPC205172
0.8176	Intermediate Similarity	NPC211158
0.8176	Intermediate Similarity	NPC39360
0.8176	Intermediate Similarity	NPC210003
0.8176	Intermediate Similarity	NPC83283
0.8176	Intermediate Similarity	NPC185103

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 NPC474620 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	765
0.2-0.3	1609
0.3-0.4	2670
0.4-0.5	2209
0.5-0.6	1168
0.6-0.7	372
0.7-0.8	92
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.825	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7685	Pre-registration
0.7875	Intermediate Similarity	NPD4380	Phase 2
0.7857	Intermediate Similarity	NPD3818	Discontinued
0.7811	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7054	Approved
0.7792	Intermediate Similarity	NPD7266	Discontinued
0.7765	Intermediate Similarity	NPD7472	Approved
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7733	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6797	Phase 2
0.7697	Intermediate Similarity	NPD7075	Discontinued
0.7674	Intermediate Similarity	NPD6559	Discontinued
0.7674	Intermediate Similarity	NPD7251	Discontinued
0.7661	Intermediate Similarity	NPD7074	Phase 3
0.763	Intermediate Similarity	NPD7808	Phase 3
0.761	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6190	Approved
0.7584	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD9545	Approved
0.7561	Intermediate Similarity	NPD6801	Discontinued
0.7532	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8312	Approved
0.7486	Intermediate Similarity	NPD8313	Approved
0.7405	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6799	Approved
0.7386	Intermediate Similarity	NPD3764	Approved
0.7378	Intermediate Similarity	NPD7458	Discontinued
0.7365	Intermediate Similarity	NPD3817	Phase 2
0.7362	Intermediate Similarity	NPD5403	Approved
0.7362	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD230	Phase 1
0.7349	Intermediate Similarity	NPD1934	Approved
0.7325	Intermediate Similarity	NPD1510	Phase 2
0.7321	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7819	Suspended
0.7305	Intermediate Similarity	NPD8455	Phase 2
0.7296	Intermediate Similarity	NPD1549	Phase 2
0.7289	Intermediate Similarity	NPD7411	Suspended
0.7262	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5402	Approved
0.725	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7799	Discontinued
0.7241	Intermediate Similarity	NPD7228	Approved
0.7239	Intermediate Similarity	NPD5401	Approved
0.7239	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6234	Discontinued
0.7233	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6599	Discontinued
0.7225	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6166	Phase 2
0.7225	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4966	Approved
0.7219	Intermediate Similarity	NPD4967	Phase 2
0.7219	Intermediate Similarity	NPD4965	Approved
0.7215	Intermediate Similarity	NPD7033	Discontinued
0.7212	Intermediate Similarity	NPD1653	Approved
0.7202	Intermediate Similarity	NPD2801	Approved
0.7181	Intermediate Similarity	NPD7435	Discontinued
0.717	Intermediate Similarity	NPD2796	Approved
0.7167	Intermediate Similarity	NPD8150	Discontinued
0.7167	Intermediate Similarity	NPD8434	Phase 2
0.7151	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD8319	Approved
0.7143	Intermediate Similarity	NPD8320	Phase 1
0.7143	Intermediate Similarity	NPD37	Approved
0.7134	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2798	Approved
0.7124	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6535	Approved
0.712	Intermediate Similarity	NPD6534	Approved
0.7118	Intermediate Similarity	NPD3882	Suspended
0.7112	Intermediate Similarity	NPD6781	Approved
0.7112	Intermediate Similarity	NPD6778	Approved
0.7112	Intermediate Similarity	NPD6782	Approved
0.7112	Intermediate Similarity	NPD6780	Approved
0.7112	Intermediate Similarity	NPD6776	Approved
0.7112	Intermediate Similarity	NPD6777	Approved
0.7112	Intermediate Similarity	NPD6779	Approved
0.7099	Intermediate Similarity	NPD3750	Approved
0.7088	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7473	Discontinued
0.7077	Intermediate Similarity	NPD7930	Approved
0.7076	Intermediate Similarity	NPD3749	Approved
0.7073	Intermediate Similarity	NPD1511	Approved
0.707	Intermediate Similarity	NPD1240	Approved
0.7063	Intermediate Similarity	NPD2935	Discontinued
0.7045	Intermediate Similarity	NPD3751	Discontinued
0.703	Intermediate Similarity	NPD2532	Approved
0.703	Intermediate Similarity	NPD2533	Approved
0.703	Intermediate Similarity	NPD2534	Approved
0.7022	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5647	Approved
0.7011	Intermediate Similarity	NPD6232	Discontinued
0.7006	Intermediate Similarity	NPD5844	Phase 1
0.7005	Intermediate Similarity	NPD7700	Phase 2
0.7005	Intermediate Similarity	NPD7699	Phase 2
0.7	Intermediate Similarity	NPD2799	Discontinued
0.6994	Remote Similarity	NPD5494	Approved
0.6988	Remote Similarity	NPD1512	Approved
0.6981	Remote Similarity	NPD1607	Approved
0.6979	Remote Similarity	NPD7584	Approved
0.6971	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7874	Approved
0.6959	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD9493	Approved
0.6928	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7999	Approved
0.6923	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7768	Phase 2
0.6918	Remote Similarity	NPD6355	Discontinued
0.6918	Remote Similarity	NPD1933	Approved
0.6914	Remote Similarity	NPD3787	Discontinued
0.6914	Remote Similarity	NPD2344	Approved
0.6911	Remote Similarity	NPD7698	Approved
0.6911	Remote Similarity	NPD7697	Approved
0.6911	Remote Similarity	NPD7696	Phase 3
0.6908	Remote Similarity	NPD1091	Approved
0.6907	Remote Similarity	NPD8151	Discontinued
0.6899	Remote Similarity	NPD6233	Phase 2
0.689	Remote Similarity	NPD8166	Discontinued
0.6889	Remote Similarity	NPD7240	Approved
0.6882	Remote Similarity	NPD6213	Phase 3
0.6882	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6212	Phase 3
0.6879	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7871	Phase 2
0.6875	Remote Similarity	NPD7870	Phase 2
0.6864	Remote Similarity	NPD3226	Approved
0.6859	Remote Similarity	NPD6823	Phase 2
0.6857	Remote Similarity	NPD6959	Discontinued
0.6856	Remote Similarity	NPD7585	Approved
0.6856	Remote Similarity	NPD7701	Phase 2
0.6852	Remote Similarity	NPD1551	Phase 2
0.6845	Remote Similarity	NPD920	Approved
0.6837	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7801	Approved
0.6837	Remote Similarity	NPD7783	Phase 2
0.6835	Remote Similarity	NPD3268	Approved
0.6835	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2313	Discontinued
0.6832	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7097	Phase 1
0.6829	Remote Similarity	NPD2800	Approved
0.6824	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6832	Phase 2
0.681	Remote Similarity	NPD6005	Phase 3
0.681	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6004	Phase 3
0.681	Remote Similarity	NPD6002	Phase 3
0.6804	Remote Similarity	NPD7583	Approved
0.6802	Remote Similarity	NPD1465	Phase 2
0.6796	Remote Similarity	NPD8368	Discontinued
0.679	Remote Similarity	NPD3748	Approved
0.6788	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6273	Approved
0.6776	Remote Similarity	NPD8407	Phase 2
0.677	Remote Similarity	NPD6653	Approved
0.677	Remote Similarity	NPD6651	Approved
0.6768	Remote Similarity	NPD2424	Discontinued
0.6753	Remote Similarity	NPD3972	Approved
0.6753	Remote Similarity	NPD9717	Approved
0.6753	Remote Similarity	NPD9269	Phase 2
0.6753	Remote Similarity	NPD1608	Approved
0.6752	Remote Similarity	NPD9494	Approved
0.675	Remote Similarity	NPD943	Approved
0.6747	Remote Similarity	NPD3887	Approved
0.6747	Remote Similarity	NPD2354	Approved
0.6747	Remote Similarity	NPD2309	Approved
0.6743	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD969	Suspended
0.6731	Remote Similarity	NPD2797	Approved
0.6731	Remote Similarity	NPD1203	Approved
0.673	Remote Similarity	NPD6798	Discontinued
0.6727	Remote Similarity	NPD1652	Phase 2
0.6727	Remote Similarity	NPD1243	Approved
0.6726	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD447	Suspended
0.6708	Remote Similarity	NPD5124	Phase 1
0.6707	Remote Similarity	NPD2346	Discontinued
0.6707	Remote Similarity	NPD7236	Approved
0.6707	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5761	Phase 2
0.6705	Remote Similarity	NPD5760	Phase 2
0.6687	Remote Similarity	NPD6663	Approved
0.6687	Remote Similarity	NPD4308	Phase 3
0.6687	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)

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