NPASS Compound

Structure

NPC21305 OpenBabel07101719252D 30 31 0 0 0 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 5 1 0 0 0 0 4 16 2 0 0 0 0 5 17 1 0 0 0 0 6 12 1 0 0 0 0 6 17 2 0 0 0 0 7 10 1 0 0 0 0 7 18 2 0 0 0 0 8 11 2 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 19 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 25 1 0 0 0 0 19 26 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 22 1 0 0 0 0 21 24 2 0 0 0 0 22 27 2 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.19
Volume:	441.43
LogP:	4.284
LogD:	3.091
LogS:	-3.75
# Rotatable Bonds:	8
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.283
Synthetic Accessibility Score:	3.003
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.823
MDCK Permeability:	1.836046067182906e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	100.82107543945312%
Volume Distribution (VD):	0.306
Pgp-substrate:	0.3531871438026428%

ADMET: Metabolism

CYP1A2-inhibitor:	0.762
CYP1A2-substrate:	0.248
CYP2C19-inhibitor:	0.768
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.879
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.901
CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.593
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	5.004
Half-life (T1/2):	0.923

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.069
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.945
Carcinogencity:	0.611
Eye Corrosion:	0.003
Eye Irritation:	0.824
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC21305

Natural Product ID:	NPC21305
*Common Name:**	Xanthokeismins A
IUPAC Name:	(E)-1-[2,4-dihydroxy-3-[(2E,5E)-7-hydroxy-3,7-dimethylocta-2,5-dienyl]phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	QJCKCZSARZRFFO-OILXWVNISA-N
Standard InCHI:	InChI=1S/C25H28O5/c1-17(5-4-16-25(2,3)30)6-12-20-23(28)15-13-21(24(20)29)22(27)14-9-18-7-10-19(26)11-8-18/h4,6-11,13-16,26,28-30H,5,12H2,1-3H3/b14-9+,16-4+,17-6+
SMILES:	C/C(=CCc1c(O)ccc(c1O)C(=O)/C=C/c1ccc(cc1)O)/C/C=C/C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503569
PubChem CID:	24970763
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003509] 3-prenylated chalcones

*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
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	exudates	n.a.	n.a.	PMID[16441065]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[18558745]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21824777]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[25891102]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21056	Angelica keiskei	Species	Apiaceae	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
NPT2	Others	Unspecified		IC50	=	510.0	nM	PMID[486219]

☑ 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 NPC21305 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	325
0.1-0.2	1498
0.2-0.3	3860
0.3-0.4	11205
0.4-0.5	7927
0.5-0.6	5062
0.6-0.7	6699
0.7-0.8	4622
0.8-0.85	949
0.85-0.9	414
0.9-0.95	113
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9918	High Similarity	NPC474998
0.9917	High Similarity	NPC30501
0.9917	High Similarity	NPC23126
0.9917	High Similarity	NPC72158
0.9917	High Similarity	NPC190043
0.9917	High Similarity	NPC103356
0.9917	High Similarity	NPC266689
0.9917	High Similarity	NPC98254
0.9917	High Similarity	NPC169250
0.9917	High Similarity	NPC162612
0.9917	High Similarity	NPC105157
0.9917	High Similarity	NPC100067
0.9836	High Similarity	NPC221777
0.9836	High Similarity	NPC473017
0.9835	High Similarity	NPC62952
0.9835	High Similarity	NPC267846
0.9754	High Similarity	NPC116513
0.96	High Similarity	NPC475042
0.9504	High Similarity	NPC133909
0.9504	High Similarity	NPC91105
0.9504	High Similarity	NPC32032
0.9504	High Similarity	NPC309765
0.9449	High Similarity	NPC139074
0.9449	High Similarity	NPC40524
0.9449	High Similarity	NPC213485
0.944	High Similarity	NPC476119
0.9431	High Similarity	NPC475733
0.9426	High Similarity	NPC65761
0.9426	High Similarity	NPC472029
0.9421	High Similarity	NPC73532
0.9421	High Similarity	NPC215392
0.9421	High Similarity	NPC267552
0.9421	High Similarity	NPC143427
0.9421	High Similarity	NPC19174
0.9421	High Similarity	NPC303737
0.9421	High Similarity	NPC156139
0.9421	High Similarity	NPC45438
0.9421	High Similarity	NPC196976
0.9421	High Similarity	NPC115159
0.9421	High Similarity	NPC224273
0.9421	High Similarity	NPC242895
0.9375	High Similarity	NPC166480
0.9375	High Similarity	NPC282780
0.9339	High Similarity	NPC297186
0.9339	High Similarity	NPC149246
0.9302	High Similarity	NPC283590
0.9302	High Similarity	NPC70859
0.9302	High Similarity	NPC130899
0.9302	High Similarity	NPC61153
0.9302	High Similarity	NPC470210
0.9291	High Similarity	NPC275504
0.9256	High Similarity	NPC159525
0.9237	High Similarity	NPC317119
0.9231	High Similarity	NPC194764
0.9231	High Similarity	NPC264112
0.9231	High Similarity	NPC65005
0.9231	High Similarity	NPC131039
0.9219	High Similarity	NPC175738
0.92	High Similarity	NPC8745
0.9194	High Similarity	NPC13238
0.918	High Similarity	NPC229649
0.9174	High Similarity	NPC161617
0.9174	High Similarity	NPC158222
0.9174	High Similarity	NPC195262
0.9174	High Similarity	NPC188814
0.9167	High Similarity	NPC21350
0.916	High Similarity	NPC150399
0.916	High Similarity	NPC168105
0.916	High Similarity	NPC477242
0.916	High Similarity	NPC477244
0.916	High Similarity	NPC1486
0.916	High Similarity	NPC41461
0.916	High Similarity	NPC274109
0.916	High Similarity	NPC249606
0.916	High Similarity	NPC66349
0.916	High Similarity	NPC98115
0.916	High Similarity	NPC25287
0.916	High Similarity	NPC12165
0.916	High Similarity	NPC186838
0.916	High Similarity	NPC477243
0.9134	High Similarity	NPC109123
0.9134	High Similarity	NPC92624
0.912	High Similarity	NPC10926
0.9106	High Similarity	NPC226275
0.9098	High Similarity	NPC294037
0.9091	High Similarity	NPC209486
0.9091	High Similarity	NPC153979
0.9091	High Similarity	NPC472419
0.9091	High Similarity	NPC40649
0.9084	High Similarity	NPC13575
0.9084	High Similarity	NPC156092
0.9077	High Similarity	NPC475088
0.9062	High Similarity	NPC259942
0.9032	High Similarity	NPC232708
0.903	High Similarity	NPC235239
0.9024	High Similarity	NPC146642
0.9023	High Similarity	NPC138099
0.9023	High Similarity	NPC19622
0.9023	High Similarity	NPC242994
0.9023	High Similarity	NPC112789
0.9015	High Similarity	NPC44960
0.9015	High Similarity	NPC474110
0.9008	High Similarity	NPC103842
0.9008	High Similarity	NPC121259
0.9008	High Similarity	NPC286336
0.8984	High Similarity	NPC102829
0.8984	High Similarity	NPC120488
0.8963	High Similarity	NPC147688
0.8963	High Similarity	NPC64908
0.8963	High Similarity	NPC156590
0.8963	High Similarity	NPC118840
0.8963	High Similarity	NPC205006
0.8955	High Similarity	NPC470211
0.8955	High Similarity	NPC472366
0.8955	High Similarity	NPC477956
0.8955	High Similarity	NPC275903
0.8955	High Similarity	NPC169452
0.8955	High Similarity	NPC181560
0.8939	High Similarity	NPC118919
0.8939	High Similarity	NPC191976
0.8931	High Similarity	NPC188646
0.8931	High Similarity	NPC18877
0.8931	High Similarity	NPC56031
0.8931	High Similarity	NPC294593
0.8931	High Similarity	NPC204960
0.8931	High Similarity	NPC242294
0.8931	High Similarity	NPC312318
0.8931	High Similarity	NPC263670
0.8931	High Similarity	NPC27643
0.8931	High Similarity	NPC472365
0.8931	High Similarity	NPC144051
0.8931	High Similarity	NPC139813
0.8931	High Similarity	NPC82225
0.8931	High Similarity	NPC192304
0.8931	High Similarity	NPC159623
0.8931	High Similarity	NPC337373
0.8931	High Similarity	NPC28753
0.8931	High Similarity	NPC175098
0.8931	High Similarity	NPC20560
0.8923	High Similarity	NPC262359
0.8898	High Similarity	NPC473751
0.8898	High Similarity	NPC328983
0.8897	High Similarity	NPC11561
0.8897	High Similarity	NPC226636
0.8897	High Similarity	NPC144499
0.8889	High Similarity	NPC219917
0.8889	High Similarity	NPC259166
0.8889	High Similarity	NPC144118
0.8889	High Similarity	NPC80962
0.8889	High Similarity	NPC48624
0.8889	High Similarity	NPC213659
0.8889	High Similarity	NPC326109
0.8889	High Similarity	NPC172250
0.8889	High Similarity	NPC475680
0.8889	High Similarity	NPC172986
0.8889	High Similarity	NPC270883
0.8889	High Similarity	NPC204985
0.8889	High Similarity	NPC305355
0.8889	High Similarity	NPC215311
0.8889	High Similarity	NPC11056
0.8889	High Similarity	NPC261227
0.8889	High Similarity	NPC69769
0.8881	High Similarity	NPC251681
0.8881	High Similarity	NPC243528
0.8881	High Similarity	NPC472903
0.8881	High Similarity	NPC471620
0.8872	High Similarity	NPC471905
0.8872	High Similarity	NPC53206
0.8872	High Similarity	NPC213603
0.8872	High Similarity	NPC290030
0.8872	High Similarity	NPC53414
0.8871	High Similarity	NPC248363
0.8855	High Similarity	NPC212631
0.8855	High Similarity	NPC267205
0.8855	High Similarity	NPC257756
0.8855	High Similarity	NPC87231
0.8855	High Similarity	NPC129132
0.8855	High Similarity	NPC205468
0.8832	High Similarity	NPC166138
0.8832	High Similarity	NPC38219
0.8832	High Similarity	NPC106985
0.8832	High Similarity	NPC18585
0.8828	High Similarity	NPC316625
0.8828	High Similarity	NPC329205
0.8824	High Similarity	NPC52789
0.8824	High Similarity	NPC110969
0.8824	High Similarity	NPC193555
0.8824	High Similarity	NPC103362
0.8824	High Similarity	NPC55832
0.8824	High Similarity	NPC321980
0.8824	High Similarity	NPC268204
0.8824	High Similarity	NPC469404
0.8824	High Similarity	NPC470087
0.8824	High Similarity	NPC470089
0.8824	High Similarity	NPC26051
0.8819	High Similarity	NPC477454
0.8815	High Similarity	NPC295384
0.8815	High Similarity	NPC216978
0.8815	High Similarity	NPC96565
0.8815	High Similarity	NPC303633

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 NPC21305 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	948
0.2-0.3	1363
0.3-0.4	2765
0.4-0.5	2152
0.5-0.6	1128
0.6-0.7	355
0.7-0.8	110
0.8-0.85	11
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8797	High Similarity	NPD1509	Clinical (unspecified phase)
0.8779	High Similarity	NPD943	Approved
0.8779	High Similarity	NPD1240	Approved
0.8647	High Similarity	NPD1607	Approved
0.8633	High Similarity	NPD7410	Clinical (unspecified phase)
0.8519	High Similarity	NPD1510	Phase 2
0.85	High Similarity	NPD4378	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD7390	Discontinued
0.8333	Intermediate Similarity	NPD1549	Phase 2
0.8261	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8244	Intermediate Similarity	NPD1164	Approved
0.8207	Intermediate Similarity	NPD4380	Phase 2
0.8151	Intermediate Similarity	NPD7411	Suspended
0.8125	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD1470	Approved
0.8077	Intermediate Similarity	NPD1201	Approved
0.8058	Intermediate Similarity	NPD5406	Approved
0.8058	Intermediate Similarity	NPD2796	Approved
0.8058	Intermediate Similarity	NPD2935	Discontinued
0.8058	Intermediate Similarity	NPD5405	Approved
0.8058	Intermediate Similarity	NPD5404	Approved
0.8058	Intermediate Similarity	NPD5408	Approved
0.8041	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7075	Discontinued
0.7987	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD6651	Approved
0.7919	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7819	Suspended
0.7917	Intermediate Similarity	NPD6799	Approved
0.7852	Intermediate Similarity	NPD6801	Discontinued
0.7823	Intermediate Similarity	NPD74	Approved
0.7823	Intermediate Similarity	NPD9266	Approved
0.7793	Intermediate Similarity	NPD1511	Approved
0.7769	Intermediate Similarity	NPD846	Approved
0.7769	Intermediate Similarity	NPD940	Approved
0.7762	Intermediate Similarity	NPD2800	Approved
0.7762	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD9493	Approved
0.7742	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD9267	Approved
0.7742	Intermediate Similarity	NPD9264	Approved
0.7742	Intermediate Similarity	NPD9263	Approved
0.7733	Intermediate Similarity	NPD1934	Approved
0.773	Intermediate Similarity	NPD2799	Discontinued
0.7718	Intermediate Similarity	NPD6599	Discontinued
0.7708	Intermediate Similarity	NPD3750	Approved
0.7697	Intermediate Similarity	NPD7768	Phase 2
0.7697	Intermediate Similarity	NPD3882	Suspended
0.7692	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1512	Approved
0.7682	Intermediate Similarity	NPD2801	Approved
0.7647	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3749	Approved
0.7639	Intermediate Similarity	NPD1243	Approved
0.7622	Intermediate Similarity	NPD2344	Approved
0.7615	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1203	Approved
0.7564	Intermediate Similarity	NPD6232	Discontinued
0.7554	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD7473	Discontinued
0.7518	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD6959	Discontinued
0.75	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD9545	Approved
0.7481	Intermediate Similarity	NPD9269	Phase 2
0.7462	Intermediate Similarity	NPD9281	Approved
0.7453	Intermediate Similarity	NPD5953	Discontinued
0.7444	Intermediate Similarity	NPD9268	Approved
0.7438	Intermediate Similarity	NPD7286	Phase 2
0.7438	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2313	Discontinued
0.7429	Intermediate Similarity	NPD3764	Approved
0.7419	Intermediate Similarity	NPD9261	Approved
0.7415	Intermediate Similarity	NPD2309	Approved
0.74	Intermediate Similarity	NPD920	Approved
0.7365	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3748	Approved
0.7358	Intermediate Similarity	NPD6166	Phase 2
0.7358	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2860	Approved
0.7355	Intermediate Similarity	NPD2859	Approved
0.7353	Intermediate Similarity	NPD9717	Approved
0.7353	Intermediate Similarity	NPD3972	Approved
0.7329	Intermediate Similarity	NPD6020	Phase 2
0.7325	Intermediate Similarity	NPD5494	Approved
0.729	Intermediate Similarity	NPD3817	Phase 2
0.7286	Intermediate Similarity	NPD6832	Phase 2
0.7285	Intermediate Similarity	NPD5403	Approved
0.7279	Intermediate Similarity	NPD2654	Approved
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD2934	Approved
0.7273	Intermediate Similarity	NPD2933	Approved
0.7267	Intermediate Similarity	NPD3818	Discontinued
0.7267	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD1242	Phase 1
0.7256	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3300	Phase 2
0.7209	Intermediate Similarity	NPD4750	Phase 3
0.7195	Intermediate Similarity	NPD6559	Discontinued
0.7192	Intermediate Similarity	NPD6100	Approved
0.7192	Intermediate Similarity	NPD6099	Approved
0.719	Intermediate Similarity	NPD3226	Approved
0.7183	Intermediate Similarity	NPD3268	Approved
0.7178	Intermediate Similarity	NPD7074	Phase 3
0.7177	Intermediate Similarity	NPD3020	Approved
0.7153	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5401	Approved
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7134	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2932	Approved
0.7132	Intermediate Similarity	NPD3019	Approved
0.7132	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4308	Phase 3
0.7117	Intermediate Similarity	NPD7054	Approved
0.7114	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4628	Phase 3
0.7087	Intermediate Similarity	NPD1237	Approved
0.7078	Intermediate Similarity	NPD7458	Discontinued
0.7073	Intermediate Similarity	NPD7472	Approved
0.7071	Intermediate Similarity	NPD2797	Approved
0.7063	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD919	Approved
0.703	Intermediate Similarity	NPD6797	Phase 2
0.7029	Intermediate Similarity	NPD422	Phase 1
0.7014	Intermediate Similarity	NPD520	Approved
0.7012	Intermediate Similarity	NPD5844	Phase 1
0.7008	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1929	Approved
0.7008	Intermediate Similarity	NPD1930	Approved
0.7007	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD3400	Discontinued
0.6988	Remote Similarity	NPD7251	Discontinued
0.6975	Remote Similarity	NPD3926	Phase 2
0.697	Remote Similarity	NPD1729	Discontinued
0.6962	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5402	Approved
0.6957	Remote Similarity	NPD1247	Approved
0.6946	Remote Similarity	NPD7808	Phase 3
0.694	Remote Similarity	NPD5951	Approved
0.6935	Remote Similarity	NPD1809	Phase 2
0.6923	Remote Similarity	NPD4908	Phase 1
0.6914	Remote Similarity	NPD5710	Approved
0.6914	Remote Similarity	NPD5711	Approved
0.6911	Remote Similarity	NPD845	Approved
0.6883	Remote Similarity	NPD5049	Phase 3
0.6879	Remote Similarity	NPD1876	Approved
0.6875	Remote Similarity	NPD4625	Phase 3
0.6861	Remote Similarity	NPD1548	Phase 1
0.6857	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2296	Approved
0.6849	Remote Similarity	NPD4307	Phase 2
0.6845	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6190	Approved
0.6842	Remote Similarity	NPD2354	Approved
0.6839	Remote Similarity	NPD4363	Phase 3
0.6839	Remote Similarity	NPD4360	Phase 2
0.6831	Remote Similarity	NPD3266	Approved
0.6831	Remote Similarity	NPD3267	Approved
0.6828	Remote Similarity	NPD411	Approved
0.6821	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3022	Approved
0.6818	Remote Similarity	NPD3021	Approved
0.6815	Remote Similarity	NPD6585	Discontinued
0.6803	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1933	Approved
0.6803	Remote Similarity	NPD5124	Phase 1
0.6803	Remote Similarity	NPD447	Suspended
0.6803	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4361	Phase 2
0.68	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1471	Phase 3
0.6792	Remote Similarity	NPD1465	Phase 2
0.6786	Remote Similarity	NPD1610	Phase 2
0.6784	Remote Similarity	NPD8150	Discontinued
0.6783	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1196	Approved
0.6772	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5048	Discontinued
0.6761	Remote Similarity	NPD3225	Approved
0.6753	Remote Similarity	NPD1543	Discontinued
0.675	Remote Similarity	NPD4288	Approved
0.6742	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD1241	Discontinued
0.6739	Remote Similarity	NPD1759	Phase 1
0.6738	Remote Similarity	NPD1608	Approved
0.6726	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3026	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