NPASS Compound

Structure

NPC471823 OpenBabel07101718312D 46 49 0 0 1 0 0 0 0 0999 V2000 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 2.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 10.0951 0.1010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8704 1.3258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3540 -0.8649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9045 1.5846 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 8.4221 -0.3473 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9033 5.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4550 4.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1292 0.3598 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6468 -1.5720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6809 -1.3132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8692 5.4483 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 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 0 0 0 0 0 0 0 0 0 0 6.4209 3.7753 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6456 2.5505 0.0000 C 0 0 0 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 7.1280 4.4824 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.9057 -2.5379 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9738 -2.0203 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5763 6.1554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3527 3.2576 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 8.0939 4.2235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0656 5.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 6.6797 2.8093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 31 1 0 0 0 0 3 42 1 0 0 0 0 4 43 1 0 0 0 0 5 8 2 0 0 0 0 5 16 1 0 0 0 0 6 9 2 0 0 0 0 6 16 1 0 0 0 0 7 10 2 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 26 1 0 0 0 0 10 27 1 0 0 0 0 11 16 2 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 13 22 2 0 0 0 0 13 23 1 0 0 0 0 14 21 1 0 0 0 0 14 32 1 0 0 0 0 15 24 1 0 0 0 0 15 32 1 0 0 0 0 17 23 2 0 0 0 0 17 29 1 0 0 0 0 18 22 1 0 0 0 0 18 29 2 0 0 0 0 19 20 2 0 0 0 0 19 33 1 0 0 0 0 20 34 1 0 0 0 0 21 28 1 0 0 0 0 21 35 1 1 0 0 0 22 42 1 0 0 0 0 23 44 1 0 0 0 0 24 28 1 0 0 0 0 24 45 1 6 0 0 0 25 12 1 1 0 0 0 25 31 1 0 0 0 0 25 46 1 0 0 0 0 26 36 2 0 0 0 0 26 45 1 0 0 0 0 27 37 2 0 0 0 0 27 44 1 0 0 0 0 28 38 1 1 0 0 0 29 43 1 0 0 0 0 30 32 1 0 0 0 0 30 39 2 0 0 0 0 30 46 1 0 0 0 0 31 40 1 0 0 0 0 32 41 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	644.21
Volume:	621.864
LogP:	2.287
LogD:	0.906
LogS:	-2.738
# Rotatable Bonds:	12
TPSA:	222.65
# H-Bond Aceptor:	14
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.079
Synthetic Accessibility Score:	4.734
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:	-6.124
MDCK Permeability:	4.033153163618408e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.413
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115
Plasma Protein Binding (PPB):	92.19754791259766%
Volume Distribution (VD):	0.721
Pgp-substrate:	13.264913558959961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.201
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.519
CYP2C9-substrate:	0.844
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.475
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	8.709
Half-life (T1/2):	0.735

ADMET: Toxicity

hERG Blockers:	0.302
Human Hepatotoxicity (H-HT):	0.5
Drug-inuced Liver Injury (DILI):	0.492
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.191
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.2
Carcinogencity:	0.426
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.057

Download Data

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

Natural Product: NPC471823

Natural Product ID:	NPC471823
*Common Name:**	3'''-O-Demethyltoddalin A
IUPAC Name:	[(2S)-1-(5,7-dimethoxy-2-oxochromen-6-yl)-3-hydroxy-3-methylbutan-2-yl] (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylate
Synonyms:
Standard InCHIKey:	CUNNJWDUTDVNSE-ASGIRPLNSA-N
Standard InCHI:	InChI=1S/C32H36O14/c1-31(2,40)25(12-18-22(42-3)13-23-17(29(18)43-4)7-10-27(37)44-23)46-30(39)32(41)14-21(35)28(38)24(15-32)45-26(36)9-6-16-5-8-19(33)20(34)11-16/h5-11,13,21,24-25,28,33-35,38,40-41H,12,14-15H2,1-4H3/b9-6+/t21-,24-,25+,28-,32+/m1/s1
SMILES:	CC(C)(C(CC1=C(C=C2C(=C1OC)C=CC(=O)O2)OC)OC(=O)C3(CC(C(C(C3)OC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3235990
PubChem CID:	90655366
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives [CHEMONTID:0002509] Cyclitols and derivatives [CHEMONTID:0002512] Quinic acids and derivatives

*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
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597921]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7213	Toddalia asiatica	Species	Rutaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1464	Individual Protein	Phosphodiesterase 4D	Homo sapiens	IC50	=	16650.0	nM	PMID[470914]

☑ 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 NPC471823 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	412
0.1-0.2	1667
0.2-0.3	3629
0.3-0.4	8615
0.4-0.5	9598
0.5-0.6	4546
0.6-0.7	5064
0.7-0.8	5092
0.8-0.85	2546
0.85-0.9	1452
0.9-0.95	75
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9172	High Similarity	NPC19380
0.9172	High Similarity	NPC146277
0.9108	High Similarity	NPC93498
0.9108	High Similarity	NPC163883
0.9068	High Similarity	NPC24164
0.9	High Similarity	NPC470896
0.9	High Similarity	NPC473275
0.9	High Similarity	NPC165483
0.8963	High Similarity	NPC142614
0.8957	High Similarity	NPC476371
0.8957	High Similarity	NPC476372
0.8951	High Similarity	NPC53889
0.8944	High Similarity	NPC68324
0.8944	High Similarity	NPC38779
0.8944	High Similarity	NPC114179
0.8944	High Similarity	NPC156818
0.8944	High Similarity	NPC289322
0.8944	High Similarity	NPC160512
0.8938	High Similarity	NPC145425
0.8909	High Similarity	NPC13481
0.8909	High Similarity	NPC207575
0.8896	High Similarity	NPC124747
0.8896	High Similarity	NPC109061
0.8896	High Similarity	NPC155754
0.8889	High Similarity	NPC98083
0.8889	High Similarity	NPC24339
0.8889	High Similarity	NPC87317
0.8889	High Similarity	NPC94220
0.8889	High Similarity	NPC7543
0.8889	High Similarity	NPC166456
0.8882	High Similarity	NPC318432
0.8882	High Similarity	NPC88803
0.8882	High Similarity	NPC250436
0.8882	High Similarity	NPC104983
0.8882	High Similarity	NPC291948
0.8882	High Similarity	NPC300845
0.8876	High Similarity	NPC67629
0.8876	High Similarity	NPC79736
0.8869	High Similarity	NPC476374
0.8862	High Similarity	NPC180768
0.8861	High Similarity	NPC103116
0.8855	High Similarity	NPC158761
0.8855	High Similarity	NPC260266
0.8848	High Similarity	NPC471788
0.8834	High Similarity	NPC476373
0.8824	High Similarity	NPC267549
0.881	High Similarity	NPC475669
0.881	High Similarity	NPC271848
0.881	High Similarity	NPC262580
0.881	High Similarity	NPC289396
0.881	High Similarity	NPC81332
0.881	High Similarity	NPC212038
0.881	High Similarity	NPC476370
0.8802	High Similarity	NPC217378
0.8802	High Similarity	NPC280493
0.8795	High Similarity	NPC9309
0.8795	High Similarity	NPC471213
0.8788	High Similarity	NPC472625
0.878	High Similarity	NPC289771
0.8758	High Similarity	NPC8712
0.8757	High Similarity	NPC98583
0.875	High Similarity	NPC75695
0.8743	High Similarity	NPC470456
0.8742	High Similarity	NPC21184
0.8742	High Similarity	NPC294522
0.8742	High Similarity	NPC120426
0.8742	High Similarity	NPC306343
0.8742	High Similarity	NPC205727
0.8735	High Similarity	NPC470457
0.8735	High Similarity	NPC50960
0.8734	High Similarity	NPC139839
0.8734	High Similarity	NPC187398
0.8734	High Similarity	NPC476348
0.8727	High Similarity	NPC471745
0.8726	High Similarity	NPC98356
0.8721	High Similarity	NPC6709
0.8721	High Similarity	NPC117668
0.8721	High Similarity	NPC208069
0.8718	High Similarity	NPC471824
0.8706	High Similarity	NPC169645
0.8706	High Similarity	NPC84482
0.8698	High Similarity	NPC65333
0.8698	High Similarity	NPC100251
0.8696	High Similarity	NPC474656
0.8683	High Similarity	NPC470462
0.8683	High Similarity	NPC43065
0.8679	High Similarity	NPC42464
0.8679	High Similarity	NPC107636
0.8679	High Similarity	NPC176903
0.8679	High Similarity	NPC30688
0.8675	High Similarity	NPC234004
0.8675	High Similarity	NPC470459
0.8675	High Similarity	NPC227297
0.8671	High Similarity	NPC476347
0.8667	High Similarity	NPC112418
0.8667	High Similarity	NPC177100
0.8667	High Similarity	NPC198829
0.8667	High Similarity	NPC349525
0.8667	High Similarity	NPC472634
0.8667	High Similarity	NPC471499
0.8667	High Similarity	NPC142252
0.8667	High Similarity	NPC139540
0.8667	High Similarity	NPC26326
0.8667	High Similarity	NPC474038
0.8659	High Similarity	NPC117418
0.8659	High Similarity	NPC53545
0.8659	High Similarity	NPC22192
0.8654	High Similarity	NPC472016
0.8654	High Similarity	NPC43158
0.8654	High Similarity	NPC277315
0.8654	High Similarity	NPC192831
0.8654	High Similarity	NPC258469
0.8647	High Similarity	NPC163165
0.8639	High Similarity	NPC476365
0.8634	High Similarity	NPC120774
0.8634	High Similarity	NPC95498
0.8634	High Similarity	NPC264875
0.8634	High Similarity	NPC163598
0.8634	High Similarity	NPC246566
0.8631	High Similarity	NPC243877
0.8631	High Similarity	NPC295082
0.8631	High Similarity	NPC473818
0.8625	High Similarity	NPC473091
0.8623	High Similarity	NPC62261
0.8623	High Similarity	NPC85057
0.8623	High Similarity	NPC130920
0.8621	High Similarity	NPC470416
0.8616	High Similarity	NPC192568
0.8616	High Similarity	NPC43123
0.8616	High Similarity	NPC471076
0.8614	High Similarity	NPC476247
0.8614	High Similarity	NPC8300
0.8614	High Similarity	NPC474033
0.8614	High Similarity	NPC220912
0.8614	High Similarity	NPC472448
0.8614	High Similarity	NPC474034
0.8614	High Similarity	NPC261470
0.8614	High Similarity	NPC83922
0.8608	High Similarity	NPC268515
0.8608	High Similarity	NPC40222
0.8608	High Similarity	NPC287275
0.8606	High Similarity	NPC475784
0.8606	High Similarity	NPC301089
0.8606	High Similarity	NPC24627
0.8606	High Similarity	NPC470326
0.8606	High Similarity	NPC328102
0.8606	High Similarity	NPC476980
0.8606	High Similarity	NPC282009
0.8606	High Similarity	NPC192686
0.8606	High Similarity	NPC119209
0.8606	High Similarity	NPC287328
0.8606	High Similarity	NPC472630
0.8606	High Similarity	NPC118256
0.8606	High Similarity	NPC470183
0.8606	High Similarity	NPC471744
0.8606	High Similarity	NPC472631
0.8605	High Similarity	NPC35167
0.8605	High Similarity	NPC476773
0.8605	High Similarity	NPC168584
0.8599	High Similarity	NPC471763
0.8598	High Similarity	NPC237418
0.8598	High Similarity	NPC125495
0.8596	High Similarity	NPC99591
0.8596	High Similarity	NPC477848
0.859	High Similarity	NPC13818
0.859	High Similarity	NPC297517
0.859	High Similarity	NPC206095
0.859	High Similarity	NPC471027
0.859	High Similarity	NPC224389
0.859	High Similarity	NPC477335
0.859	High Similarity	NPC35702
0.8589	High Similarity	NPC222185
0.8588	High Similarity	NPC121333
0.8588	High Similarity	NPC190003
0.8588	High Similarity	NPC175107
0.858	High Similarity	NPC475212
0.858	High Similarity	NPC177480
0.8563	High Similarity	NPC241781
0.8563	High Similarity	NPC36138
0.8563	High Similarity	NPC156785
0.8563	High Similarity	NPC41301
0.8563	High Similarity	NPC162394
0.8563	High Similarity	NPC45943
0.8563	High Similarity	NPC124038
0.8562	High Similarity	NPC475250
0.8554	High Similarity	NPC472632
0.8554	High Similarity	NPC471210
0.8554	High Similarity	NPC471211
0.8554	High Similarity	NPC473106
0.8554	High Similarity	NPC29876
0.8554	High Similarity	NPC308992
0.8554	High Similarity	NPC158188
0.8554	High Similarity	NPC167678
0.8554	High Similarity	NPC228383
0.8554	High Similarity	NPC259456
0.8554	High Similarity	NPC3629
0.8554	High Similarity	NPC471212
0.8554	High Similarity	NPC103201
0.8554	High Similarity	NPC134783
0.8553	High Similarity	NPC15577

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 NPC471823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	932
0.2-0.3	1903
0.3-0.4	2594
0.4-0.5	1904
0.5-0.6	925
0.6-0.7	340
0.7-0.8	136
0.8-0.85	28
0.85-0.9	24
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8882	High Similarity	NPD4868	Clinical (unspecified phase)
0.8698	High Similarity	NPD7993	Clinical (unspecified phase)
0.858	High Similarity	NPD5844	Phase 1
0.8535	High Similarity	NPD6190	Approved
0.8512	High Similarity	NPD6168	Clinical (unspecified phase)
0.8512	High Similarity	NPD6167	Clinical (unspecified phase)
0.8512	High Similarity	NPD6166	Phase 2
0.8488	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD7075	Discontinued
0.8415	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD3817	Phase 2
0.8354	Intermediate Similarity	NPD6801	Discontinued
0.8343	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD7251	Discontinued
0.8304	Intermediate Similarity	NPD3818	Discontinued
0.8303	Intermediate Similarity	NPD2801	Approved
0.8303	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD7808	Phase 3
0.8266	Intermediate Similarity	NPD6797	Phase 2
0.8256	Intermediate Similarity	NPD7054	Approved
0.8256	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5402	Approved
0.8242	Intermediate Similarity	NPD1934	Approved
0.8232	Intermediate Similarity	NPD4380	Phase 2
0.8208	Intermediate Similarity	NPD7472	Approved
0.8208	Intermediate Similarity	NPD7074	Phase 3
0.8204	Intermediate Similarity	NPD3882	Suspended
0.8193	Intermediate Similarity	NPD1465	Phase 2
0.811	Intermediate Similarity	NPD1653	Approved
0.8098	Intermediate Similarity	NPD1512	Approved
0.8084	Intermediate Similarity	NPD7819	Suspended
0.807	Intermediate Similarity	NPD6232	Discontinued
0.8047	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD7473	Discontinued
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6234	Discontinued
0.7989	Intermediate Similarity	NPD7228	Approved
0.7975	Intermediate Similarity	NPD1511	Approved
0.7964	Intermediate Similarity	NPD7411	Suspended
0.7953	Intermediate Similarity	NPD5494	Approved
0.7939	Intermediate Similarity	NPD5403	Approved
0.7929	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD37	Approved
0.7907	Intermediate Similarity	NPD7199	Phase 2
0.7901	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1613	Approved
0.7886	Intermediate Similarity	NPD3751	Discontinued
0.7885	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4967	Phase 2
0.7882	Intermediate Similarity	NPD4966	Approved
0.7882	Intermediate Similarity	NPD4965	Approved
0.7882	Intermediate Similarity	NPD7768	Phase 2
0.7866	Intermediate Similarity	NPD6799	Approved
0.7818	Intermediate Similarity	NPD5401	Approved
0.7809	Intermediate Similarity	NPD7685	Pre-registration
0.7803	Intermediate Similarity	NPD8127	Discontinued
0.7791	Intermediate Similarity	NPD919	Approved
0.7771	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD3787	Discontinued
0.7742	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD230	Phase 1
0.7736	Intermediate Similarity	NPD5124	Phase 1
0.7736	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD6559	Discontinued
0.7707	Intermediate Similarity	NPD3027	Phase 3
0.7692	Intermediate Similarity	NPD8150	Discontinued
0.7692	Intermediate Similarity	NPD6599	Discontinued
0.7692	Intermediate Similarity	NPD8434	Phase 2
0.7683	Intermediate Similarity	NPD4628	Phase 3
0.7683	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3750	Approved
0.7661	Intermediate Similarity	NPD8455	Phase 2
0.7658	Intermediate Similarity	NPD6798	Discontinued
0.7643	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6233	Phase 2
0.7607	Intermediate Similarity	NPD7266	Discontinued
0.76	Intermediate Similarity	NPD1247	Approved
0.76	Intermediate Similarity	NPD6959	Discontinued
0.758	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1549	Phase 2
0.7557	Intermediate Similarity	NPD7229	Phase 3
0.7546	Intermediate Similarity	NPD2796	Approved
0.7546	Intermediate Similarity	NPD2935	Discontinued
0.7545	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3749	Approved
0.7527	Intermediate Similarity	NPD8312	Approved
0.7527	Intermediate Similarity	NPD8313	Approved
0.7516	Intermediate Similarity	NPD6355	Discontinued
0.7514	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7435	Discontinued
0.7485	Intermediate Similarity	NPD7033	Discontinued
0.7485	Intermediate Similarity	NPD1510	Phase 2
0.7473	Intermediate Similarity	NPD7549	Discontinued
0.7453	Intermediate Similarity	NPD4060	Phase 1
0.7438	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3226	Approved
0.7412	Intermediate Similarity	NPD920	Approved
0.7411	Intermediate Similarity	NPD7783	Phase 2
0.7411	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1652	Phase 2
0.7396	Intermediate Similarity	NPD2534	Approved
0.7396	Intermediate Similarity	NPD2532	Approved
0.7396	Intermediate Similarity	NPD2533	Approved
0.7378	Intermediate Similarity	NPD3748	Approved
0.7375	Intermediate Similarity	NPD7095	Approved
0.7365	Intermediate Similarity	NPD8166	Discontinued
0.736	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7874	Approved
0.7349	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7585	Approved
0.7344	Intermediate Similarity	NPD6781	Approved
0.7344	Intermediate Similarity	NPD6782	Approved
0.7344	Intermediate Similarity	NPD6779	Approved
0.7344	Intermediate Similarity	NPD6776	Approved
0.7344	Intermediate Similarity	NPD6777	Approved
0.7344	Intermediate Similarity	NPD6778	Approved
0.7344	Intermediate Similarity	NPD6780	Approved
0.7342	Intermediate Similarity	NPD2797	Approved
0.7333	Intermediate Similarity	NPD6100	Approved
0.7333	Intermediate Similarity	NPD6099	Approved
0.7329	Intermediate Similarity	NPD3268	Approved
0.7326	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7697	Approved
0.732	Intermediate Similarity	NPD7696	Phase 3
0.732	Intermediate Similarity	NPD7698	Approved
0.7318	Intermediate Similarity	NPD3926	Phase 2
0.7317	Intermediate Similarity	NPD7097	Phase 1
0.7312	Intermediate Similarity	NPD4908	Phase 1
0.731	Intermediate Similarity	NPD8151	Discontinued
0.7308	Intermediate Similarity	NPD422	Phase 1
0.7301	Intermediate Similarity	NPD447	Suspended
0.7296	Intermediate Similarity	NPD7583	Approved
0.7294	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7870	Phase 2
0.7282	Intermediate Similarity	NPD7871	Phase 2
0.7278	Intermediate Similarity	NPD3225	Approved
0.7268	Intermediate Similarity	NPD5953	Discontinued
0.7259	Intermediate Similarity	NPD7701	Phase 2
0.7253	Intermediate Similarity	NPD7286	Phase 2
0.7239	Intermediate Similarity	NPD1240	Approved
0.7239	Intermediate Similarity	NPD943	Approved
0.7231	Intermediate Similarity	NPD7680	Approved
0.7229	Intermediate Similarity	NPD1551	Phase 2
0.7225	Intermediate Similarity	NPD7458	Discontinued
0.7202	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1243	Approved
0.7176	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4308	Phase 3
0.716	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1607	Approved
0.7151	Intermediate Similarity	NPD6273	Approved
0.715	Intermediate Similarity	NPD7700	Phase 2
0.715	Intermediate Similarity	NPD7801	Approved
0.715	Intermediate Similarity	NPD7699	Phase 2
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7127	Intermediate Similarity	NPD5242	Approved
0.7121	Intermediate Similarity	NPD7584	Approved
0.7119	Intermediate Similarity	NPD5353	Approved
0.7117	Intermediate Similarity	NPD2313	Discontinued
0.7112	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8320	Phase 1
0.7107	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8319	Approved
0.7101	Intermediate Similarity	NPD6674	Discontinued
0.7099	Intermediate Similarity	NPD6832	Phase 2
0.7088	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5762	Approved
0.7083	Intermediate Similarity	NPD6535	Approved
0.7083	Intermediate Similarity	NPD5763	Approved
0.7083	Intermediate Similarity	NPD6534	Approved
0.7077	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4062	Phase 3
0.7066	Intermediate Similarity	NPD2799	Discontinued
0.7055	Intermediate Similarity	NPD4625	Phase 3
0.7051	Intermediate Similarity	NPD1548	Phase 1
0.7045	Intermediate Similarity	NPD6386	Approved
0.7045	Intermediate Similarity	NPD6385	Approved
0.7044	Intermediate Similarity	NPD9269	Phase 2
0.7044	Intermediate Similarity	NPD1608	Approved
0.7043	Intermediate Similarity	NPD7039	Approved
0.7043	Intermediate Similarity	NPD7038	Approved
0.7041	Intermediate Similarity	NPD2493	Approved
0.7041	Intermediate Similarity	NPD2494	Approved
0.7037	Intermediate Similarity	NPD9494	Approved
0.7019	Intermediate Similarity	NPD3267	Approved
0.7019	Intermediate Similarity	NPD3266	Approved
0.7012	Intermediate Similarity	NPD1296	Phase 2
0.7012	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6823	Phase 2
0.7005	Intermediate Similarity	NPD8155	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