NPASS Compound

Structure

NPC272841 OpenBabel07101719242D 27 28 0 0 1 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5000 0.8660 0.0000 C 0 0 1 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 5.1962 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -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 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 -0.5000 -0.8660 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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 19 1 0 0 0 0 7 10 1 0 0 0 0 7 12 1 0 0 0 0 8 12 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 19 1 6 0 0 0 11 2 1 1 0 0 0 11 21 1 0 0 0 0 12 26 1 1 0 0 0 13 9 1 1 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 6 0 0 0 15 16 1 0 0 0 0 15 23 1 1 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 26 1 1 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 19 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.24
Volume:	390.389
LogP:	0.296
LogD:	0.013
LogS:	-2.048
# Rotatable Bonds:	6
TPSA:	139.84
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.356
Synthetic Accessibility Score:	4.785
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.244
MDCK Permeability:	0.00010705443855840713
Pgp-inhibitor:	0.292
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.683
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.075

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148
Plasma Protein Binding (PPB):	25.423297882080078%
Volume Distribution (VD):	0.407
Pgp-substrate:	57.66144943237305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.656
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.176
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.057

ADMET: Excretion

Clearance (CL):	1.672
Half-life (T1/2):	0.677

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.263
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.189
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.259
Skin Sensitization:	0.497
Carcinogencity:	0.108
Eye Corrosion:	0.004
Eye Irritation:	0.11
Respiratory Toxicity:	0.133

Download Data

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

Natural Product: NPC272841

Natural Product ID:	NPC272841
*Common Name:**	Iso-Dihydrodendranthemoside A
IUPAC Name:	(2S,3S,4R,5R,6S)-2-[(1S,4R,5S)-4-hydroxy-4-[(3S)-3-hydroxybutyl]-3,3,5-trimethylcyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	Iso-Dihydrodendranthemoside A
Standard InCHIKey:	ARLXZLBJVXNRGP-GFFWZXEVSA-N
Standard InCHI:	InChI=1S/C19H36O8/c1-10-7-12(8-18(3,4)19(10,25)6-5-11(2)21)26-17-16(24)15(23)14(22)13(9-20)27-17/h10-17,20-25H,5-9H2,1-4H3/t10-,11-,12-,13-,14-,15+,16-,17-,19+/m0/s1
SMILES:	C[C@H]1C[C@@H](CC(C)(C)[C@]1(CC[C@H](C)O)O)O[C@@H]1[C@H]([C@@H]([C@H]([C@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1770694
PubChem CID:	54582814
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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
NPO5829	Distylium racemosum	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21489793]
NPO5829	Distylium racemosum	Species	Hamamelidaceae	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	8

Activity Type	# Activity
Individual Protein	2
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3046	Individual Protein	Ribonuclease HI	Escherichia coli (strain K12)	IC50	>	20000.0	nM	PMID[513598]
NPT2	Others	Unspecified		IC50	>	20000.0	nM	PMID[513598]

☑ 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 NPC272841 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	520
0.1-0.2	4229
0.2-0.3	10998
0.3-0.4	13031
0.4-0.5	5881
0.5-0.6	5311
0.6-0.7	2339
0.7-0.8	353
0.8-0.85	29
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC308489
0.9351	High Similarity	NPC241959
0.92	High Similarity	NPC177343
0.8919	High Similarity	NPC166250
0.8767	High Similarity	NPC471879
0.8765	High Similarity	NPC268633
0.8765	High Similarity	NPC471411
0.8765	High Similarity	NPC471410
0.8659	High Similarity	NPC140446
0.8659	High Similarity	NPC43912
0.8659	High Similarity	NPC472396
0.8642	High Similarity	NPC290612
0.8537	High Similarity	NPC107603
0.8519	High Similarity	NPC474156
0.8452	Intermediate Similarity	NPC82955
0.8452	Intermediate Similarity	NPC131466
0.8372	Intermediate Similarity	NPC171741
0.8372	Intermediate Similarity	NPC470623
0.8372	Intermediate Similarity	NPC18724
0.8372	Intermediate Similarity	NPC323231
0.8372	Intermediate Similarity	NPC224003
0.8353	Intermediate Similarity	NPC279329
0.8333	Intermediate Similarity	NPC281004
0.8293	Intermediate Similarity	NPC18953
0.8276	Intermediate Similarity	NPC148593
0.8276	Intermediate Similarity	NPC77717
0.8276	Intermediate Similarity	NPC267238
0.8276	Intermediate Similarity	NPC471373
0.8276	Intermediate Similarity	NPC253611
0.8256	Intermediate Similarity	NPC36372
0.8256	Intermediate Similarity	NPC210759
0.8256	Intermediate Similarity	NPC293609
0.8256	Intermediate Similarity	NPC307167
0.8256	Intermediate Similarity	NPC229801
0.825	Intermediate Similarity	NPC186588
0.8235	Intermediate Similarity	NPC473472
0.8235	Intermediate Similarity	NPC102725
0.8214	Intermediate Similarity	NPC45833
0.8214	Intermediate Similarity	NPC62202
0.8214	Intermediate Similarity	NPC110365
0.8214	Intermediate Similarity	NPC213658
0.8205	Intermediate Similarity	NPC107963
0.8182	Intermediate Similarity	NPC471425
0.8182	Intermediate Similarity	NPC189575
0.8182	Intermediate Similarity	NPC471424
0.8182	Intermediate Similarity	NPC471429
0.8182	Intermediate Similarity	NPC477494
0.8182	Intermediate Similarity	NPC205129
0.8182	Intermediate Similarity	NPC106701
0.8161	Intermediate Similarity	NPC167644
0.8161	Intermediate Similarity	NPC311246
0.8161	Intermediate Similarity	NPC277774
0.814	Intermediate Similarity	NPC474249
0.814	Intermediate Similarity	NPC261990
0.814	Intermediate Similarity	NPC65550
0.814	Intermediate Similarity	NPC223143
0.814	Intermediate Similarity	NPC473542
0.8118	Intermediate Similarity	NPC470872
0.8108	Intermediate Similarity	NPC477760
0.8108	Intermediate Similarity	NPC477759
0.8108	Intermediate Similarity	NPC179823
0.8108	Intermediate Similarity	NPC477754
0.8108	Intermediate Similarity	NPC477758
0.8108	Intermediate Similarity	NPC477761
0.8077	Intermediate Similarity	NPC472952
0.8077	Intermediate Similarity	NPC472950
0.8068	Intermediate Similarity	NPC151214
0.8068	Intermediate Similarity	NPC45959
0.8068	Intermediate Similarity	NPC473503
0.8068	Intermediate Similarity	NPC3538
0.8068	Intermediate Similarity	NPC191915
0.8068	Intermediate Similarity	NPC477224
0.8068	Intermediate Similarity	NPC305418
0.8068	Intermediate Similarity	NPC309866
0.8068	Intermediate Similarity	NPC113500
0.8068	Intermediate Similarity	NPC252253
0.8068	Intermediate Similarity	NPC175
0.8049	Intermediate Similarity	NPC477447
0.8049	Intermediate Similarity	NPC470155
0.8049	Intermediate Similarity	NPC477446
0.8046	Intermediate Similarity	NPC204881
0.8046	Intermediate Similarity	NPC476668
0.8046	Intermediate Similarity	NPC473830
0.8046	Intermediate Similarity	NPC5632
0.8046	Intermediate Similarity	NPC473637
0.8046	Intermediate Similarity	NPC149966
0.8023	Intermediate Similarity	NPC20822
0.8	Intermediate Similarity	NPC477577
0.7978	Intermediate Similarity	NPC94582
0.7978	Intermediate Similarity	NPC473065
0.7978	Intermediate Similarity	NPC469710
0.7978	Intermediate Similarity	NPC92196
0.7978	Intermediate Similarity	NPC57964
0.7978	Intermediate Similarity	NPC473064
0.7978	Intermediate Similarity	NPC473067
0.7976	Intermediate Similarity	NPC235402
0.7973	Intermediate Similarity	NPC477764
0.7973	Intermediate Similarity	NPC477751
0.7973	Intermediate Similarity	NPC477752
0.7973	Intermediate Similarity	NPC477756
0.7955	Intermediate Similarity	NPC172838
0.7955	Intermediate Similarity	NPC475307
0.7955	Intermediate Similarity	NPC149400
0.7955	Intermediate Similarity	NPC473726
0.7955	Intermediate Similarity	NPC137004
0.7955	Intermediate Similarity	NPC88962
0.7955	Intermediate Similarity	NPC144790
0.7955	Intermediate Similarity	NPC476669
0.7949	Intermediate Similarity	NPC200167
0.7949	Intermediate Similarity	NPC31046
0.7949	Intermediate Similarity	NPC53868
0.7949	Intermediate Similarity	NPC470151
0.7949	Intermediate Similarity	NPC209666
0.7927	Intermediate Similarity	NPC470156
0.7927	Intermediate Similarity	NPC470154
0.7927	Intermediate Similarity	NPC71541
0.7912	Intermediate Similarity	NPC209798
0.7912	Intermediate Similarity	NPC471375
0.7912	Intermediate Similarity	NPC471374
0.7889	Intermediate Similarity	NPC139271
0.7889	Intermediate Similarity	NPC472989
0.7889	Intermediate Similarity	NPC237071
0.7889	Intermediate Similarity	NPC203434
0.7889	Intermediate Similarity	NPC473287
0.7889	Intermediate Similarity	NPC304011
0.7889	Intermediate Similarity	NPC476510
0.7889	Intermediate Similarity	NPC238796
0.7889	Intermediate Similarity	NPC252056
0.7889	Intermediate Similarity	NPC90583
0.7889	Intermediate Similarity	NPC142264
0.7882	Intermediate Similarity	NPC471240
0.7875	Intermediate Similarity	NPC188793
0.7865	Intermediate Similarity	NPC24960
0.7865	Intermediate Similarity	NPC179859
0.7865	Intermediate Similarity	NPC131693
0.7865	Intermediate Similarity	NPC174024
0.7865	Intermediate Similarity	NPC72817
0.7865	Intermediate Similarity	NPC475325
0.7865	Intermediate Similarity	NPC30687
0.7865	Intermediate Similarity	NPC477927
0.7865	Intermediate Similarity	NPC473851
0.7865	Intermediate Similarity	NPC253268
0.7865	Intermediate Similarity	NPC475436
0.7865	Intermediate Similarity	NPC291547
0.7865	Intermediate Similarity	NPC312678
0.7865	Intermediate Similarity	NPC473774
0.7857	Intermediate Similarity	NPC166279
0.7841	Intermediate Similarity	NPC289361
0.7841	Intermediate Similarity	NPC59006
0.7826	Intermediate Similarity	NPC471428
0.7826	Intermediate Similarity	NPC471426
0.7826	Intermediate Similarity	NPC51579
0.7826	Intermediate Similarity	NPC471427
0.7805	Intermediate Similarity	NPC471216
0.7805	Intermediate Similarity	NPC472951
0.7805	Intermediate Similarity	NPC471217
0.7805	Intermediate Similarity	NPC472943
0.7802	Intermediate Similarity	NPC233649
0.7802	Intermediate Similarity	NPC477223
0.7802	Intermediate Similarity	NPC470028
0.7802	Intermediate Similarity	NPC477222
0.7791	Intermediate Similarity	NPC210658
0.7791	Intermediate Similarity	NPC161928
0.7778	Intermediate Similarity	NPC474399
0.7753	Intermediate Similarity	NPC141769
0.7753	Intermediate Similarity	NPC325828
0.7753	Intermediate Similarity	NPC477547
0.7753	Intermediate Similarity	NPC48339
0.7753	Intermediate Similarity	NPC297348
0.7753	Intermediate Similarity	NPC250393
0.7753	Intermediate Similarity	NPC477451
0.7753	Intermediate Similarity	NPC234352
0.7753	Intermediate Similarity	NPC249204
0.7753	Intermediate Similarity	NPC177834
0.775	Intermediate Similarity	NPC279575
0.7738	Intermediate Similarity	NPC470070
0.7738	Intermediate Similarity	NPC474346
0.7738	Intermediate Similarity	NPC474253
0.7738	Intermediate Similarity	NPC474284
0.7738	Intermediate Similarity	NPC213737
0.7738	Intermediate Similarity	NPC475820
0.7717	Intermediate Similarity	NPC473638
0.7717	Intermediate Similarity	NPC312325
0.7711	Intermediate Similarity	NPC16090
0.7701	Intermediate Similarity	NPC128475
0.7692	Intermediate Similarity	NPC296936
0.7692	Intermediate Similarity	NPC121453
0.7667	Intermediate Similarity	NPC305160
0.7667	Intermediate Similarity	NPC291203
0.7667	Intermediate Similarity	NPC471464
0.7667	Intermediate Similarity	NPC222731
0.7667	Intermediate Similarity	NPC217205
0.7667	Intermediate Similarity	NPC264101
0.7667	Intermediate Similarity	NPC294686
0.7662	Intermediate Similarity	NPC470833
0.766	Intermediate Similarity	NPC214277
0.766	Intermediate Similarity	NPC150463
0.7619	Intermediate Similarity	NPC208912
0.7619	Intermediate Similarity	NPC470611
0.7619	Intermediate Similarity	NPC2096

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 NPC272841 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	575
0.1-0.2	4283
0.2-0.3	2852
0.3-0.4	838
0.4-0.5	340
0.5-0.6	212
0.6-0.7	45
0.7-0.8	5
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
0.8026	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1810	Approved
0.7949	Intermediate Similarity	NPD1811	Approved
0.7753	Intermediate Similarity	NPD8171	Discontinued
0.7564	Intermediate Similarity	NPD2687	Approved
0.7564	Intermediate Similarity	NPD2254	Approved
0.7564	Intermediate Similarity	NPD2686	Approved
0.7467	Intermediate Similarity	NPD371	Approved
0.7326	Intermediate Similarity	NPD3669	Approved
0.7326	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6928	Phase 2
0.7	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD2269	Approved
0.6606	Remote Similarity	NPD7516	Approved
0.6604	Remote Similarity	NPD8133	Approved
0.6575	Remote Similarity	NPD888	Phase 3
0.6575	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD893	Approved
0.6575	Remote Similarity	NPD891	Phase 3
0.6575	Remote Similarity	NPD892	Phase 3
0.6528	Remote Similarity	NPD905	Approved
0.6528	Remote Similarity	NPD904	Phase 3
0.6517	Remote Similarity	NPD1780	Approved
0.6517	Remote Similarity	NPD1779	Approved
0.6442	Remote Similarity	NPD6686	Approved
0.6422	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6123	Approved
0.6396	Remote Similarity	NPD8294	Approved
0.6396	Remote Similarity	NPD8377	Approved
0.6351	Remote Similarity	NPD889	Approved
0.6351	Remote Similarity	NPD894	Approved
0.6351	Remote Similarity	NPD895	Approved
0.6351	Remote Similarity	NPD887	Approved
0.6346	Remote Similarity	NPD6412	Phase 2
0.6339	Remote Similarity	NPD8378	Approved
0.6339	Remote Similarity	NPD8033	Approved
0.6339	Remote Similarity	NPD8296	Approved
0.6339	Remote Similarity	NPD8380	Approved
0.6339	Remote Similarity	NPD8335	Approved
0.6339	Remote Similarity	NPD8379	Approved
0.6316	Remote Similarity	NPD2267	Suspended
0.6286	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD7503	Approved
0.6182	Remote Similarity	NPD6940	Discontinued
0.618	Remote Similarity	NPD6697	Approved
0.618	Remote Similarity	NPD6114	Approved
0.618	Remote Similarity	NPD6118	Approved
0.618	Remote Similarity	NPD6115	Approved
0.6162	Remote Similarity	NPD7991	Discontinued
0.6121	Remote Similarity	NPD7507	Approved
0.6087	Remote Similarity	NPD8328	Phase 3
0.6082	Remote Similarity	NPD3168	Discontinued
0.6067	Remote Similarity	NPD6116	Phase 1
0.6053	Remote Similarity	NPD7346	Approved
0.5981	Remote Similarity	NPD8174	Phase 2
0.5966	Remote Similarity	NPD7319	Approved
0.5962	Remote Similarity	NPD8084	Approved
0.5962	Remote Similarity	NPD8138	Approved
0.5962	Remote Similarity	NPD8086	Approved
0.5962	Remote Similarity	NPD8083	Approved
0.5962	Remote Similarity	NPD8082	Approved
0.5962	Remote Similarity	NPD8139	Approved
0.5962	Remote Similarity	NPD8085	Approved
0.5955	Remote Similarity	NPD6117	Approved
0.5938	Remote Similarity	NPD7524	Approved
0.593	Remote Similarity	NPD4787	Phase 1
0.5926	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD8276	Approved
0.5905	Remote Similarity	NPD8275	Approved
0.587	Remote Similarity	NPD7525	Registered
0.5865	Remote Similarity	NPD5344	Discontinued
0.5862	Remote Similarity	NPD6370	Approved
0.5849	Remote Similarity	NPD8081	Approved
0.5843	Remote Similarity	NPD3703	Phase 2
0.5833	Remote Similarity	NPD8997	Approved
0.5833	Remote Similarity	NPD9000	Phase 3
0.5833	Remote Similarity	NPD8998	Phase 2
0.5833	Remote Similarity	NPD8999	Phase 3
0.5833	Remote Similarity	NPD8993	Phase 1
0.5794	Remote Similarity	NPD8393	Approved
0.5789	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6921	Approved
0.5761	Remote Similarity	NPD7645	Phase 2
0.5753	Remote Similarity	NPD385	Approved
0.5753	Remote Similarity	NPD384	Approved
0.5741	Remote Similarity	NPD8307	Discontinued
0.5741	Remote Similarity	NPD8140	Approved
0.573	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1700	Approved
0.5701	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.569	Remote Similarity	NPD6054	Approved
0.569	Remote Similarity	NPD6059	Approved
0.5684	Remote Similarity	NPD6695	Phase 3
0.5682	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD8966	Approved
0.5676	Remote Similarity	NPD8965	Approved
0.5667	Remote Similarity	NPD8293	Discontinued
0.5663	Remote Similarity	NPD847	Phase 1
0.5648	Remote Similarity	NPD5357	Phase 1
0.5636	Remote Similarity	NPD8305	Approved
0.5636	Remote Similarity	NPD8306	Approved
0.5632	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD369	Approved
0.562	Remote Similarity	NPD7736	Approved
0.5618	Remote Similarity	NPD3181	Approved
0.5616	Remote Similarity	NPD388	Approved
0.5616	Remote Similarity	NPD386	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