NPASS Compound

Structure

NPC179862 OpenBabel07101719152D 53 60 0 0 1 0 0 0 0 0999 V2000 11.0713 -2.6552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7705 -4.3610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 -2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0561 -2.8289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7554 -4.5346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1554 -3.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3801 -2.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3801 1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1554 2.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1473 -1.7870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7749 -1.1946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8009 -4.0137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4936 -1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4285 -3.4213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3981 -3.7686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1213 -3.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1213 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7901 -1.0209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4893 -2.7267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8161 -3.8400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4437 -3.2476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1169 -2.1343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8356 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 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 7.4741 -2.9003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1364 1.2057 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1212 1.0321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4936 0.4397 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6428 -1.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6428 0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4632 0.0924 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.3830 -3.9422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8284 -3.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8284 2.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8465 -3.4927 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1733 -4.6061 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7944 2.1454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7640 1.7981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1428 -2.6321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1428 1.6321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6276 -1.9397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4480 -0.0813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1017 -2.3079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8204 -0.6736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6276 0.9397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 17 2 0 0 0 0 2 8 2 0 0 0 0 2 17 1 0 0 0 0 3 9 1 0 0 0 0 3 18 2 0 0 0 0 4 10 2 0 0 0 0 4 18 1 0 0 0 0 5 11 1 0 0 0 0 5 19 2 0 0 0 0 6 12 2 0 0 0 0 6 19 1 0 0 0 0 7 20 2 0 0 0 0 8 20 1 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 23 2 0 0 0 0 13 24 1 0 0 0 0 14 23 1 0 0 0 0 14 27 2 0 0 0 0 15 25 1 0 0 0 0 15 26 2 0 0 0 0 16 49 1 0 0 0 0 17 26 1 0 0 0 0 20 40 1 0 0 0 0 21 41 1 0 0 0 0 22 42 1 0 0 0 0 23 50 1 0 0 0 0 24 31 2 0 0 0 0 24 43 1 0 0 0 0 25 31 1 0 0 0 0 25 44 2 0 0 0 0 26 51 1 0 0 0 0 27 31 1 0 0 0 0 27 51 1 0 0 0 0 28 16 1 6 0 0 0 28 36 1 0 0 0 0 28 52 1 0 0 0 0 29 18 1 6 0 0 0 29 30 1 0 0 0 0 29 32 1 0 0 0 0 30 19 1 6 0 0 0 30 33 1 0 0 0 0 32 33 1 0 0 0 0 32 37 1 1 0 0 0 33 38 1 1 0 0 0 34 35 1 0 0 0 0 34 36 1 0 0 0 0 34 45 1 6 0 0 0 35 39 1 0 0 0 0 35 46 1 1 0 0 0 36 53 1 1 0 0 0 37 47 2 0 0 0 0 37 49 1 0 0 0 0 38 48 2 0 0 0 0 38 53 1 0 0 0 0 39 50 1 6 0 0 0 39 52 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	724.18
Volume:	695.528
LogP:	4.124
LogD:	1.788
LogS:	-4.978
# Rotatable Bonds:	5
TPSA:	222.65
# H-Bond Aceptor:	14
# H-Bond Donor:	6
# Rings:	8
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.143
Synthetic Accessibility Score:	5.364
Fsp3:	0.256
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:	-5.896
MDCK Permeability:	8.236955181928352e-06
Pgp-inhibitor:	0.068
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.781
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	96.84101104736328%
Volume Distribution (VD):	0.796
Pgp-substrate:	2.6949386596679688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.048
CYP2C19-inhibitor:	0.36
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.388
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.749
CYP2D6-substrate:	0.278
CYP3A4-inhibitor:	0.813
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	4.195
Half-life (T1/2):	0.092

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.909
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.639
Rat Oral Acute Toxicity:	0.546
Maximum Recommended Daily Dose:	0.645
Skin Sensitization:	0.787
Carcinogencity:	0.151
Eye Corrosion:	0.003
Eye Irritation:	0.081
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC179862

Natural Product ID:	NPC179862
*Common Name:**	Itoside N
IUPAC Name:	n.a.
Synonyms:	Itoside N
Standard InCHIKey:	FJUGWGGYGGSGCO-FAXYJIGKSA-N
Standard InCHI:	InChI=1S/C39H32O14/c40-20-7-1-17(2-8-20)26-15-25(44)31-24(43)13-23(14-27(31)51-26)50-39-35(46)34(45)36-28(52-39)16-49-37(47)32-29(18-3-9-21(41)10-4-18)30(33(32)38(48)53-36)19-5-11-22(42)12-6-19/h1-15,28-30,32-36,39-43,45-46H,16H2/t28-,29-,30+,32+,33-,34-,35-,36-,39-/m1/s1
SMILES:	c1cc(ccc1c1cc(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@H]2[C@@H](COC(=O)[C@H]3[C@H](c4ccc(cc4)O)[C@H](c4ccc(cc4)O)[C@H]3C(=O)O2)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448212
PubChem CID:	24879215
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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
NPO9317	Itoa orientalis	Species	Salicaceae	Eukaryota	bark, twigs, and leaves	n.a.	n.a.	PMID[18412396]
NPO9317	Itoa orientalis	Species	Salicaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	67.3	%	PMID[554329]

☑ 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 NPC179862 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	463
0.1-0.2	1801
0.2-0.3	4079
0.3-0.4	9497
0.4-0.5	9408
0.5-0.6	4893
0.6-0.7	5932
0.7-0.8	5382
0.8-0.85	890
0.85-0.9	338
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9337	High Similarity	NPC473278
0.9337	High Similarity	NPC260504
0.9337	High Similarity	NPC89809
0.929	High Similarity	NPC168789
0.9172	High Similarity	NPC188815
0.9172	High Similarity	NPC96605
0.9172	High Similarity	NPC218161
0.9172	High Similarity	NPC280642
0.9172	High Similarity	NPC76047
0.9118	High Similarity	NPC217822
0.9118	High Similarity	NPC221288
0.9118	High Similarity	NPC101399
0.9118	High Similarity	NPC11847
0.9096	High Similarity	NPC472994
0.9096	High Similarity	NPC270675
0.9096	High Similarity	NPC195685
0.9096	High Similarity	NPC210961
0.9096	High Similarity	NPC477628
0.9096	High Similarity	NPC477629
0.9059	High Similarity	NPC469344
0.9042	High Similarity	NPC472876
0.9029	High Similarity	NPC75574
0.8988	High Similarity	NPC80068
0.8982	High Similarity	NPC101636
0.8976	High Similarity	NPC308265
0.8971	High Similarity	NPC132111
0.8971	High Similarity	NPC473717
0.8971	High Similarity	NPC473631
0.8971	High Similarity	NPC293227
0.8971	High Similarity	NPC475662
0.8966	High Similarity	NPC471030
0.896	High Similarity	NPC231787
0.8947	High Similarity	NPC164704
0.8947	High Similarity	NPC470712
0.8947	High Similarity	NPC92815
0.8935	High Similarity	NPC129264
0.8935	High Similarity	NPC205824
0.8935	High Similarity	NPC85751
0.8935	High Similarity	NPC19240
0.8935	High Similarity	NPC139060
0.8929	High Similarity	NPC298171
0.8927	High Similarity	NPC65489
0.8922	High Similarity	NPC271479
0.8922	High Similarity	NPC473623
0.892	High Similarity	NPC231254
0.8916	High Similarity	NPC156457
0.8916	High Similarity	NPC258035
0.8916	High Similarity	NPC161749
0.8916	High Similarity	NPC197896
0.8916	High Similarity	NPC313163
0.8895	High Similarity	NPC474522
0.8895	High Similarity	NPC470715
0.8895	High Similarity	NPC470714
0.8895	High Similarity	NPC470716
0.8882	High Similarity	NPC298666
0.8882	High Similarity	NPC262222
0.8882	High Similarity	NPC68592
0.8876	High Similarity	NPC257566
0.8876	High Similarity	NPC124155
0.8876	High Similarity	NPC473644
0.887	High Similarity	NPC221140
0.887	High Similarity	NPC229817
0.887	High Similarity	NPC475352
0.887	High Similarity	NPC475220
0.887	High Similarity	NPC473686
0.8869	High Similarity	NPC282169
0.8869	High Similarity	NPC47923
0.8869	High Similarity	NPC470125
0.8869	High Similarity	NPC97812
0.8869	High Similarity	NPC303913
0.8864	High Similarity	NPC321916
0.8864	High Similarity	NPC135831
0.8864	High Similarity	NPC297503
0.8864	High Similarity	NPC97119
0.8862	High Similarity	NPC43761
0.8862	High Similarity	NPC138811
0.8862	High Similarity	NPC22062
0.8862	High Similarity	NPC73511
0.8862	High Similarity	NPC473634
0.8855	High Similarity	NPC127406
0.8852	High Similarity	NPC470450
0.8848	High Similarity	NPC143851
0.8848	High Similarity	NPC29763
0.8848	High Similarity	NPC39360
0.8848	High Similarity	NPC83283
0.8848	High Similarity	NPC210003
0.8824	High Similarity	NPC294722
0.8817	High Similarity	NPC27942
0.8817	High Similarity	NPC44947
0.8817	High Similarity	NPC475382
0.8814	High Similarity	NPC106700
0.8814	High Similarity	NPC318119
0.881	High Similarity	NPC246469
0.881	High Similarity	NPC97285
0.881	High Similarity	NPC271270
0.881	High Similarity	NPC142860
0.8807	High Similarity	NPC475161
0.8807	High Similarity	NPC477860
0.8802	High Similarity	NPC65003
0.8802	High Similarity	NPC271741
0.8802	High Similarity	NPC322459
0.8802	High Similarity	NPC323627
0.8802	High Similarity	NPC318527
0.8802	High Similarity	NPC473512
0.8802	High Similarity	NPC44931
0.8802	High Similarity	NPC287789
0.8802	High Similarity	NPC129827
0.8802	High Similarity	NPC43638
0.8802	High Similarity	NPC324358
0.8795	High Similarity	NPC26195
0.8795	High Similarity	NPC72649
0.8795	High Similarity	NPC169248
0.8795	High Similarity	NPC95090
0.8795	High Similarity	NPC39351
0.8795	High Similarity	NPC97052
0.8795	High Similarity	NPC258474
0.8795	High Similarity	NPC201227
0.8795	High Similarity	NPC27408
0.8788	High Similarity	NPC121001
0.8788	High Similarity	NPC259182
0.8786	High Similarity	NPC137871
0.8786	High Similarity	NPC288152
0.8786	High Similarity	NPC9002
0.8786	High Similarity	NPC257011
0.8786	High Similarity	NPC67134
0.8786	High Similarity	NPC47140
0.8779	High Similarity	NPC5319
0.8779	High Similarity	NPC222455
0.8778	High Similarity	NPC264302
0.8772	High Similarity	NPC64425
0.8765	High Similarity	NPC311850
0.8765	High Similarity	NPC63438
0.8764	High Similarity	NPC474093
0.8764	High Similarity	NPC104910
0.8764	High Similarity	NPC87583
0.8757	High Similarity	NPC175513
0.8757	High Similarity	NPC159579
0.8757	High Similarity	NPC224530
0.8757	High Similarity	NPC259957
0.8757	High Similarity	NPC85707
0.8757	High Similarity	NPC129217
0.8757	High Similarity	NPC48093
0.8757	High Similarity	NPC216496
0.875	High Similarity	NPC277710
0.875	High Similarity	NPC153578
0.875	High Similarity	NPC299149
0.875	High Similarity	NPC114257
0.8743	High Similarity	NPC170475
0.8743	High Similarity	NPC295613
0.8743	High Similarity	NPC203500
0.8743	High Similarity	NPC61112
0.8743	High Similarity	NPC307938
0.8743	High Similarity	NPC206378
0.8743	High Similarity	NPC45165
0.8743	High Similarity	NPC473657
0.8743	High Similarity	NPC198489
0.8743	High Similarity	NPC323593
0.8743	High Similarity	NPC144097
0.8743	High Similarity	NPC472992
0.8743	High Similarity	NPC32867
0.8743	High Similarity	NPC261866
0.8743	High Similarity	NPC309648
0.8743	High Similarity	NPC472991
0.8743	High Similarity	NPC61904
0.8736	High Similarity	NPC175230
0.8736	High Similarity	NPC88560
0.8736	High Similarity	NPC472993
0.8736	High Similarity	NPC172033
0.8735	High Similarity	NPC106625
0.8728	High Similarity	NPC8704
0.8728	High Similarity	NPC287884
0.8728	High Similarity	NPC138990
0.8728	High Similarity	NPC209550
0.8728	High Similarity	NPC149011
0.8728	High Similarity	NPC199079
0.8728	High Similarity	NPC175429
0.8728	High Similarity	NPC204937
0.8728	High Similarity	NPC277532
0.8728	High Similarity	NPC210808
0.8721	High Similarity	NPC249977
0.8715	High Similarity	NPC475179
0.8715	High Similarity	NPC30011
0.8715	High Similarity	NPC294863
0.8715	High Similarity	NPC282636
0.8715	High Similarity	NPC72554
0.8715	High Similarity	NPC105591
0.8715	High Similarity	NPC97817
0.8713	High Similarity	NPC289667
0.8713	High Similarity	NPC76831
0.8713	High Similarity	NPC7752
0.8713	High Similarity	NPC292929
0.8713	High Similarity	NPC475979
0.8713	High Similarity	NPC135358
0.8713	High Similarity	NPC287889
0.8706	High Similarity	NPC131745
0.8706	High Similarity	NPC240306
0.8706	High Similarity	NPC190450
0.8701	High Similarity	NPC469371
0.8698	High Similarity	NPC304741
0.8698	High Similarity	NPC187379

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 NPC179862 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	928
0.2-0.3	2025
0.3-0.4	2734
0.4-0.5	1899
0.5-0.6	812
0.6-0.7	212
0.7-0.8	115
0.8-0.85	19
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8916	High Similarity	NPD4381	Clinical (unspecified phase)
0.8779	High Similarity	NPD7804	Clinical (unspecified phase)
0.8563	High Similarity	NPD7054	Approved
0.8531	High Similarity	NPD8312	Approved
0.8531	High Similarity	NPD8313	Approved
0.8514	High Similarity	NPD7472	Approved
0.8514	High Similarity	NPD7074	Phase 3
0.8475	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8475	Intermediate Similarity	NPD7808	Phase 3
0.8418	Intermediate Similarity	NPD7251	Discontinued
0.84	Intermediate Similarity	NPD3818	Discontinued
0.8362	Intermediate Similarity	NPD6797	Phase 2
0.8353	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4380	Phase 2
0.8306	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD8455	Phase 2
0.8286	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD7075	Discontinued
0.8198	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6166	Phase 2
0.8182	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD6559	Discontinued
0.8092	Intermediate Similarity	NPD7768	Phase 2
0.8081	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7411	Suspended
0.8023	Intermediate Similarity	NPD6801	Discontinued
0.8011	Intermediate Similarity	NPD6959	Discontinued
0.7977	Intermediate Similarity	NPD7819	Suspended
0.7949	Intermediate Similarity	NPD8151	Discontinued
0.7943	Intermediate Similarity	NPD3749	Approved
0.7941	Intermediate Similarity	NPD5403	Approved
0.7939	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7473	Discontinued
0.7931	Intermediate Similarity	NPD5402	Approved
0.7919	Intermediate Similarity	NPD1934	Approved
0.7892	Intermediate Similarity	NPD1549	Phase 2
0.7874	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD3817	Phase 2
0.7824	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD5401	Approved
0.7824	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7435	Discontinued
0.7771	Intermediate Similarity	NPD2801	Approved
0.7765	Intermediate Similarity	NPD6232	Discontinued
0.7765	Intermediate Similarity	NPD6799	Approved
0.7711	Intermediate Similarity	NPD1510	Phase 2
0.7701	Intermediate Similarity	NPD6599	Discontinued
0.7692	Intermediate Similarity	NPD3751	Discontinued
0.7692	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3750	Approved
0.7692	Intermediate Similarity	NPD7228	Approved
0.7688	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7783	Phase 2
0.7667	Intermediate Similarity	NPD3787	Discontinued
0.7665	Intermediate Similarity	NPD2796	Approved
0.7661	Intermediate Similarity	NPD1511	Approved
0.7653	Intermediate Similarity	NPD7871	Phase 2
0.7653	Intermediate Similarity	NPD7870	Phase 2
0.765	Intermediate Similarity	NPD5844	Phase 1
0.7644	Intermediate Similarity	NPD7458	Discontinued
0.7638	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD7874	Approved
0.7629	Intermediate Similarity	NPD6780	Approved
0.7629	Intermediate Similarity	NPD6776	Approved
0.7629	Intermediate Similarity	NPD6782	Approved
0.7629	Intermediate Similarity	NPD6781	Approved
0.7629	Intermediate Similarity	NPD6777	Approved
0.7629	Intermediate Similarity	NPD6779	Approved
0.7629	Intermediate Similarity	NPD6778	Approved
0.7622	Intermediate Similarity	NPD7685	Pre-registration
0.7611	Intermediate Similarity	NPD7199	Phase 2
0.7602	Intermediate Similarity	NPD7698	Approved
0.7602	Intermediate Similarity	NPD7696	Phase 3
0.7602	Intermediate Similarity	NPD7697	Approved
0.7572	Intermediate Similarity	NPD1512	Approved
0.7565	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD8320	Phase 1
0.7563	Intermediate Similarity	NPD8319	Approved
0.7556	Intermediate Similarity	NPD5494	Approved
0.7538	Intermediate Similarity	NPD7701	Phase 2
0.7512	Intermediate Similarity	NPD7801	Approved
0.7487	Intermediate Similarity	NPD7584	Approved
0.7486	Intermediate Similarity	NPD3882	Suspended
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7472	Intermediate Similarity	NPD1465	Phase 2
0.7471	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7699	Phase 2
0.7436	Intermediate Similarity	NPD7700	Phase 2
0.7432	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD8434	Phase 2
0.7416	Intermediate Similarity	NPD37	Approved
0.7414	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6234	Discontinued
0.7396	Intermediate Similarity	NPD3748	Approved
0.7389	Intermediate Similarity	NPD4966	Approved
0.7389	Intermediate Similarity	NPD4965	Approved
0.7389	Intermediate Similarity	NPD4967	Phase 2
0.7386	Intermediate Similarity	NPD1653	Approved
0.7374	Intermediate Similarity	NPD6823	Phase 2
0.7371	Intermediate Similarity	NPD6534	Approved
0.7371	Intermediate Similarity	NPD6535	Approved
0.7365	Intermediate Similarity	NPD1240	Approved
0.7356	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1551	Phase 2
0.7349	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7240	Approved
0.7337	Intermediate Similarity	NPD7097	Phase 1
0.733	Intermediate Similarity	NPD8150	Discontinued
0.7287	Intermediate Similarity	NPD5953	Discontinued
0.7278	Intermediate Similarity	NPD1607	Approved
0.7277	Intermediate Similarity	NPD7585	Approved
0.7247	Intermediate Similarity	NPD3226	Approved
0.7232	Intermediate Similarity	NPD920	Approved
0.7229	Intermediate Similarity	NPD4908	Phase 1
0.7228	Intermediate Similarity	NPD7583	Approved
0.7216	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2533	Approved
0.7216	Intermediate Similarity	NPD2532	Approved
0.7216	Intermediate Similarity	NPD2534	Approved
0.7193	Intermediate Similarity	NPD2799	Discontinued
0.7181	Intermediate Similarity	NPD7286	Phase 2
0.7159	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7390	Discontinued
0.7151	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD6212	Phase 3
0.7143	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6213	Phase 3
0.7126	Intermediate Similarity	NPD2800	Approved
0.712	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2344	Approved
0.7107	Intermediate Similarity	NPD4363	Phase 3
0.7107	Intermediate Similarity	NPD4360	Phase 2
0.7102	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7033	Discontinued
0.7079	Intermediate Similarity	NPD7680	Approved
0.7077	Intermediate Similarity	NPD4287	Approved
0.7072	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7930	Approved
0.7059	Intermediate Similarity	NPD3926	Phase 2
0.7052	Intermediate Similarity	NPD2935	Discontinued
0.7041	Intermediate Similarity	NPD6798	Discontinued
0.7041	Intermediate Similarity	NPD3268	Approved
0.7029	Intermediate Similarity	NPD1243	Approved
0.7024	Intermediate Similarity	NPD6832	Phase 2
0.7021	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1933	Approved
0.7018	Intermediate Similarity	NPD6355	Discontinued
0.7018	Intermediate Similarity	NPD5124	Phase 1
0.7011	Intermediate Similarity	NPD7266	Discontinued
0.7006	Intermediate Similarity	NPD2798	Approved
0.7005	Intermediate Similarity	NPD7229	Phase 3
0.6989	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6651	Approved
0.6965	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1613	Approved
0.6959	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6099	Approved
0.6954	Remote Similarity	NPD6100	Approved
0.6949	Remote Similarity	NPD6190	Approved
0.6949	Remote Similarity	NPD2309	Approved
0.6946	Remote Similarity	NPD1203	Approved
0.6946	Remote Similarity	NPD2797	Approved
0.6944	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8059	Phase 3
0.6935	Remote Similarity	NPD919	Approved
0.6932	Remote Similarity	NPD1652	Phase 2
0.6914	Remote Similarity	NPD2346	Discontinued
0.6909	Remote Similarity	NPD1091	Approved
0.6909	Remote Similarity	NPD1610	Phase 2
0.6901	Remote Similarity	NPD6233	Phase 2
0.6893	Remote Similarity	NPD7003	Approved
0.6881	Remote Similarity	NPD8285	Discontinued
0.6865	Remote Similarity	NPD4288	Approved
0.6862	Remote Similarity	NPD8127	Discontinued
0.686	Remote Similarity	NPD943	Approved
0.6859	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5408	Approved
0.6857	Remote Similarity	NPD5405	Approved
0.6857	Remote Similarity	NPD5406	Approved
0.6857	Remote Similarity	NPD5404	Approved
0.6845	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3764	Approved
0.6825	Remote Similarity	NPD5711	Approved
0.6825	Remote Similarity	NPD5710	Approved
0.6821	Remote Similarity	NPD230	Phase 1
0.6818	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6273	Approved
0.6786	Remote Similarity	NPD3225	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