NPASS Compound

Structure

CID19622 OpenBabel06191715342D 36 38 0 0 0 0 0 0 0 0999 V2000 -2.5981 -2.5000 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 2.5981 4.5000 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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 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 1.7321 -1.0000 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 -3.4641 -1.0000 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 2.5981 3.5000 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 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 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 0.8660 0.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 1 19 1 0 0 0 0 2 13 1 0 0 0 0 2 19 2 0 0 0 0 3 9 1 0 0 0 0 3 20 2 0 0 0 0 4 10 2 0 0 0 0 4 20 1 0 0 0 0 5 11 1 0 0 0 0 5 21 2 0 0 0 0 6 12 2 0 0 0 0 6 21 1 0 0 0 0 7 15 2 0 0 0 0 7 20 1 0 0 0 0 8 17 2 0 0 0 0 8 21 1 0 0 0 0 9 22 2 0 0 0 0 10 22 1 0 0 0 0 11 23 2 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 16 2 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 19 1 0 0 0 0 18 36 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 27 2 0 0 0 0 24 29 1 0 0 0 0 25 26 1 0 0 0 0 25 29 2 0 0 0 0 26 32 2 0 0 0 0 27 33 1 0 0 0 0 28 34 2 0 0 0 0 28 36 1 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.17
Volume:	509.092
LogP:	4.898
LogD:	3.594
LogS:	-3.574
# Rotatable Bonds:	10
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.143
Synthetic Accessibility Score:	2.797
Fsp3:	0.103
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:	-5.084
MDCK Permeability:	1.4168434972816613e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	101.6732406616211%
Volume Distribution (VD):	0.283
Pgp-substrate:	0.3005382716655731%

ADMET: Metabolism

CYP1A2-inhibitor:	0.76
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.917
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.878
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.833
CYP2D6-substrate:	0.884
CYP3A4-inhibitor:	0.599
CYP3A4-substrate:	0.25

ADMET: Excretion

Clearance (CL):	9.49
Half-life (T1/2):	0.942

ADMET: Toxicity

hERG Blockers:	0.114
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.196
AMES Toxicity:	0.787
Rat Oral Acute Toxicity:	0.229
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.97
Carcinogencity:	0.368
Eye Corrosion:	0.003
Eye Irritation:	0.802
Respiratory Toxicity:	0.155

Download Data

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

Natural Product: NPC19622

Natural Product ID:	NPC19622
*Common Name:**	Isogemichalcone B
IUPAC Name:	[(E)-4-[2,6-dihydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenyl]-2-methylbut-2-enyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	YKTQNXNBVRMYNF-YVMHTMGASA-N
Standard InCHI:	InChI=1S/C29H26O7/c1-19(18-36-28(34)17-8-21-5-11-23(31)12-6-21)2-13-24-27(33)16-14-25(29(24)35)26(32)15-7-20-3-9-22(30)10-4-20/h2-12,14-17,30-31,33,35H,13,18H2,1H3/b15-7+,17-8+,19-2+
SMILES:	C/C(=CCc1c(ccc(C(=O)/C=C/c2ccc(cc2)O)c1O)O)/COC(=O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517334
PubChem CID:	42607532
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
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/0031-9422(95)00135-T]
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869218]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	bark and twigs	Tewah, Central Kalimantan, Indonesia (N 38 57.003; W 094 44.767)	1999-Oct	PMID[11858749]
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217294]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Wood	n.a.	n.a.	PMID[23113717]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8352	Canthium berberidifolium	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11740	Sagenomella striatispora	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8352	Canthium berberidifolium	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	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	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	11700.0	nM	PMID[484677]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	15000.0	nM	PMID[484677]
NPT2	Others	Unspecified		IC50	=	82200.0	nM	PMID[484678]

☑ 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 NPC19622 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	310
0.1-0.2	1341
0.2-0.3	3261
0.3-0.4	7660
0.4-0.5	11279
0.5-0.6	4089
0.6-0.7	6564
0.7-0.8	5929
0.8-0.85	1566
0.85-0.9	671
0.9-0.95	24
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC112789
0.9925	High Similarity	NPC275903
0.922	High Similarity	NPC25844
0.913	High Similarity	NPC243528
0.913	High Similarity	NPC251681
0.9118	High Similarity	NPC470210
0.9104	High Similarity	NPC475042
0.9091	High Similarity	NPC105157
0.9091	High Similarity	NPC162612
0.9091	High Similarity	NPC72158
0.9091	High Similarity	NPC30501
0.9091	High Similarity	NPC103356
0.9091	High Similarity	NPC266689
0.9091	High Similarity	NPC169250
0.9091	High Similarity	NPC100067
0.9091	High Similarity	NPC190043
0.9091	High Similarity	NPC98254
0.9091	High Similarity	NPC23126
0.9065	High Similarity	NPC470986
0.9051	High Similarity	NPC131039
0.9023	High Similarity	NPC221777
0.9023	High Similarity	NPC21305
0.9023	High Similarity	NPC473017
0.9015	High Similarity	NPC62952
0.9015	High Similarity	NPC267846
0.9014	High Similarity	NPC469953
0.9	High Similarity	NPC326109
0.9	High Similarity	NPC213659
0.9	High Similarity	NPC144118
0.9	High Similarity	NPC204985
0.9	High Similarity	NPC80962
0.9	High Similarity	NPC219917
0.9	High Similarity	NPC172250
0.9	High Similarity	NPC259166
0.9	High Similarity	NPC48624
0.9	High Similarity	NPC215311
0.8986	High Similarity	NPC150399
0.8986	High Similarity	NPC274109
0.8986	High Similarity	NPC477243
0.8986	High Similarity	NPC25287
0.8986	High Similarity	NPC168105
0.8986	High Similarity	NPC249606
0.8986	High Similarity	NPC1486
0.8986	High Similarity	NPC12165
0.8986	High Similarity	NPC98115
0.8986	High Similarity	NPC66349
0.8986	High Similarity	NPC186838
0.8986	High Similarity	NPC41461
0.8986	High Similarity	NPC477242
0.8986	High Similarity	NPC477244
0.8971	High Similarity	NPC213485
0.8971	High Similarity	NPC139074
0.8971	High Similarity	NPC40524
0.8955	High Similarity	NPC476119
0.8955	High Similarity	NPC474998
0.8951	High Similarity	NPC473078
0.8951	High Similarity	NPC470133
0.8951	High Similarity	NPC470131
0.8951	High Similarity	NPC109183
0.8951	High Similarity	NPC470134
0.8951	High Similarity	NPC470132
0.8947	High Similarity	NPC116513
0.8944	High Similarity	NPC149026
0.8944	High Similarity	NPC75049
0.8944	High Similarity	NPC175504
0.8944	High Similarity	NPC310130
0.8944	High Similarity	NPC150408
0.8944	High Similarity	NPC257097
0.8944	High Similarity	NPC169591
0.8944	High Similarity	NPC221432
0.8944	High Similarity	NPC39329
0.8944	High Similarity	NPC68104
0.8944	High Similarity	NPC164980
0.8944	High Similarity	NPC143896
0.8944	High Similarity	NPC91560
0.8936	High Similarity	NPC55832
0.8936	High Similarity	NPC110969
0.8936	High Similarity	NPC469404
0.8936	High Similarity	NPC3188
0.8936	High Similarity	NPC26051
0.8936	High Similarity	NPC26238
0.8936	High Similarity	NPC52789
0.8936	High Similarity	NPC268204
0.8929	High Similarity	NPC283429
0.8929	High Similarity	NPC470211
0.8929	High Similarity	NPC295384
0.8921	High Similarity	NPC472419
0.8921	High Similarity	NPC153979
0.8921	High Similarity	NPC317119
0.8919	High Similarity	NPC471787
0.8913	High Similarity	NPC156092
0.8913	High Similarity	NPC13575
0.8904	High Similarity	NPC317715
0.8904	High Similarity	NPC204561
0.8904	High Similarity	NPC316960
0.8904	High Similarity	NPC309512
0.8904	High Similarity	NPC148945
0.8904	High Similarity	NPC78835
0.8889	High Similarity	NPC21378
0.8889	High Similarity	NPC470987
0.8881	High Similarity	NPC39045
0.8881	High Similarity	NPC470136
0.8881	High Similarity	NPC473015
0.8881	High Similarity	NPC470135
0.8881	High Similarity	NPC209040
0.8881	High Similarity	NPC197252
0.8881	High Similarity	NPC236766
0.8881	High Similarity	NPC473013
0.8873	High Similarity	NPC125855
0.8873	High Similarity	NPC107572
0.8873	High Similarity	NPC167624
0.8873	High Similarity	NPC227579
0.8873	High Similarity	NPC324436
0.8873	High Similarity	NPC220998
0.8873	High Similarity	NPC223500
0.8873	High Similarity	NPC11561
0.8873	High Similarity	NPC228504
0.8873	High Similarity	NPC64915
0.8873	High Similarity	NPC166934
0.8873	High Similarity	NPC1089
0.8873	High Similarity	NPC161506
0.8873	High Similarity	NPC177354
0.8873	High Similarity	NPC265040
0.8873	High Similarity	NPC37496
0.8873	High Similarity	NPC226636
0.8873	High Similarity	NPC32739
0.8873	High Similarity	NPC324134
0.8873	High Similarity	NPC10937
0.8873	High Similarity	NPC76338
0.8873	High Similarity	NPC328164
0.8873	High Similarity	NPC182852
0.8873	High Similarity	NPC148757
0.8873	High Similarity	NPC78
0.8873	High Similarity	NPC296917
0.8873	High Similarity	NPC166482
0.8873	High Similarity	NPC36181
0.8873	High Similarity	NPC194432
0.8873	High Similarity	NPC76372
0.8873	High Similarity	NPC306829
0.8873	High Similarity	NPC40833
0.8873	High Similarity	NPC66515
0.8865	High Similarity	NPC69769
0.8865	High Similarity	NPC101366
0.8865	High Similarity	NPC235239
0.8865	High Similarity	NPC241100
0.8865	High Similarity	NPC159275
0.8865	High Similarity	NPC172986
0.8865	High Similarity	NPC261227
0.8865	High Similarity	NPC253822
0.8865	High Similarity	NPC270883
0.8859	High Similarity	NPC35598
0.8859	High Similarity	NPC222689
0.8857	High Similarity	NPC124269
0.8857	High Similarity	NPC471620
0.8857	High Similarity	NPC21350
0.8841	High Similarity	NPC130899
0.8841	High Similarity	NPC286336
0.8841	High Similarity	NPC61153
0.8841	High Similarity	NPC103842
0.8841	High Similarity	NPC283590
0.8841	High Similarity	NPC70859
0.8836	High Similarity	NPC151973
0.8824	High Similarity	NPC275504
0.8819	High Similarity	NPC154217
0.8819	High Similarity	NPC470322
0.8819	High Similarity	NPC228779
0.8819	High Similarity	NPC470570
0.8811	High Similarity	NPC166138
0.8811	High Similarity	NPC94794
0.8811	High Similarity	NPC87609
0.8811	High Similarity	NPC18585
0.8811	High Similarity	NPC214166
0.8811	High Similarity	NPC112791
0.8811	High Similarity	NPC193703
0.8811	High Similarity	NPC117836
0.8811	High Similarity	NPC85162
0.8811	High Similarity	NPC185276
0.8811	High Similarity	NPC21599
0.8811	High Similarity	NPC188632
0.8811	High Similarity	NPC125894
0.8811	High Similarity	NPC478086
0.8811	High Similarity	NPC278249
0.8811	High Similarity	NPC196459
0.8811	High Similarity	NPC106985
0.8811	High Similarity	NPC316816
0.8811	High Similarity	NPC77794
0.8811	High Similarity	NPC476178
0.8811	High Similarity	NPC223812
0.8811	High Similarity	NPC470296
0.8811	High Similarity	NPC475705
0.8811	High Similarity	NPC81697
0.8811	High Similarity	NPC51887
0.8811	High Similarity	NPC107177
0.8803	High Similarity	NPC156590
0.8803	High Similarity	NPC110038
0.8803	High Similarity	NPC118840
0.8803	High Similarity	NPC248372
0.8803	High Similarity	NPC282300
0.8803	High Similarity	NPC312391
0.8803	High Similarity	NPC17170

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 NPC19622 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	876
0.2-0.3	1405
0.3-0.4	2507
0.4-0.5	2196
0.5-0.6	1295
0.6-0.7	422
0.7-0.8	145
0.8-0.85	21
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9034	High Similarity	NPD7411	Suspended
0.875	High Similarity	NPD7410	Clinical (unspecified phase)
0.8662	High Similarity	NPD7421	Clinical (unspecified phase)
0.8643	High Similarity	NPD1510	Phase 2
0.8623	High Similarity	NPD1240	Approved
0.8621	High Similarity	NPD4378	Clinical (unspecified phase)
0.8609	High Similarity	NPD7075	Discontinued
0.8592	High Similarity	NPD1549	Phase 2
0.8543	High Similarity	NPD7768	Phase 2
0.8533	High Similarity	NPD7096	Clinical (unspecified phase)
0.8533	High Similarity	NPD7819	Suspended
0.8521	High Similarity	NPD1550	Clinical (unspecified phase)
0.8521	High Similarity	NPD1552	Clinical (unspecified phase)
0.8516	High Similarity	NPD7852	Clinical (unspecified phase)
0.85	High Similarity	NPD1607	Approved
0.8477	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD6801	Discontinued
0.8456	Intermediate Similarity	NPD4380	Phase 2
0.8425	Intermediate Similarity	NPD6799	Approved
0.838	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD2796	Approved
0.8322	Intermediate Similarity	NPD2935	Discontinued
0.8289	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD6599	Discontinued
0.8194	Intermediate Similarity	NPD5404	Approved
0.8194	Intermediate Similarity	NPD5406	Approved
0.8194	Intermediate Similarity	NPD5408	Approved
0.8194	Intermediate Similarity	NPD5405	Approved
0.8176	Intermediate Similarity	NPD7390	Discontinued
0.8153	Intermediate Similarity	NPD6232	Discontinued
0.8129	Intermediate Similarity	NPD3749	Approved
0.8113	Intermediate Similarity	NPD7473	Discontinued
0.8099	Intermediate Similarity	NPD943	Approved
0.8095	Intermediate Similarity	NPD3750	Approved
0.8085	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD1551	Phase 2
0.806	Intermediate Similarity	NPD9545	Approved
0.8045	Intermediate Similarity	NPD9493	Approved
0.8013	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD2532	Approved
0.8	Intermediate Similarity	NPD2799	Discontinued
0.7987	Intermediate Similarity	NPD1934	Approved
0.7986	Intermediate Similarity	NPD1164	Approved
0.7975	Intermediate Similarity	NPD6959	Discontinued
0.7973	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD3764	Approved
0.7949	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD5953	Discontinued
0.7905	Intermediate Similarity	NPD1243	Approved
0.7901	Intermediate Similarity	NPD7286	Phase 2
0.7895	Intermediate Similarity	NPD5403	Approved
0.7895	Intermediate Similarity	NPD920	Approved
0.7885	Intermediate Similarity	NPD3817	Phase 2
0.7867	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6651	Approved
0.7857	Intermediate Similarity	NPD1203	Approved
0.7834	Intermediate Similarity	NPD3882	Suspended
0.7832	Intermediate Similarity	NPD2313	Discontinued
0.7826	Intermediate Similarity	NPD6166	Phase 2
0.7826	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2801	Approved
0.7817	Intermediate Similarity	NPD6832	Phase 2
0.7815	Intermediate Similarity	NPD1511	Approved
0.7793	Intermediate Similarity	NPD230	Phase 1
0.7791	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5844	Phase 1
0.7763	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD5401	Approved
0.7758	Intermediate Similarity	NPD6559	Discontinued
0.7755	Intermediate Similarity	NPD3748	Approved
0.773	Intermediate Similarity	NPD1470	Approved
0.7712	Intermediate Similarity	NPD1512	Approved
0.7698	Intermediate Similarity	NPD1201	Approved
0.7677	Intermediate Similarity	NPD3226	Approved
0.7677	Intermediate Similarity	NPD7458	Discontinued
0.7667	Intermediate Similarity	NPD2800	Approved
0.7662	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2344	Approved
0.7643	Intermediate Similarity	NPD9717	Approved
0.7622	Intermediate Similarity	NPD3818	Discontinued
0.7616	Intermediate Similarity	NPD7003	Approved
0.7616	Intermediate Similarity	NPD4628	Phase 3
0.7586	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3268	Approved
0.7586	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5494	Approved
0.7576	Intermediate Similarity	NPD9266	Approved
0.7576	Intermediate Similarity	NPD74	Approved
0.7552	Intermediate Similarity	NPD2798	Approved
0.7547	Intermediate Similarity	NPD5402	Approved
0.7533	Intermediate Similarity	NPD2346	Discontinued
0.753	Intermediate Similarity	NPD7074	Phase 3
0.7517	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9263	Approved
0.75	Intermediate Similarity	NPD9264	Approved
0.75	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9267	Approved
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2797	Approved
0.7482	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7054	Approved
0.7466	Intermediate Similarity	NPD6798	Discontinued
0.7452	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6190	Approved
0.7451	Intermediate Similarity	NPD2309	Approved
0.7448	Intermediate Similarity	NPD4908	Phase 1
0.7447	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7472	Approved
0.74	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4308	Phase 3
0.7396	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6797	Phase 2
0.7378	Intermediate Similarity	NPD5710	Approved
0.7378	Intermediate Similarity	NPD5711	Approved
0.7358	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7251	Discontinued
0.7326	Intermediate Similarity	NPD8150	Discontinued
0.7324	Intermediate Similarity	NPD422	Phase 1
0.7315	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5124	Phase 1
0.7315	Intermediate Similarity	NPD1933	Approved
0.7308	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD520	Approved
0.7294	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD9269	Phase 2
0.7273	Intermediate Similarity	NPD7229	Phase 3
0.7273	Intermediate Similarity	NPD8166	Discontinued
0.7273	Intermediate Similarity	NPD3972	Approved
0.725	Intermediate Similarity	NPD5889	Approved
0.725	Intermediate Similarity	NPD5890	Approved
0.7246	Intermediate Similarity	NPD9281	Approved
0.7241	Intermediate Similarity	NPD3267	Approved
0.7241	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3266	Approved
0.7234	Intermediate Similarity	NPD9268	Approved
0.7208	Intermediate Similarity	NPD2654	Approved
0.7197	Intermediate Similarity	NPD9261	Approved
0.7192	Intermediate Similarity	NPD1019	Discontinued
0.7181	Intermediate Similarity	NPD6233	Phase 2
0.7179	Intermediate Similarity	NPD7440	Discontinued
0.7172	Intermediate Similarity	NPD3225	Approved
0.7163	Intermediate Similarity	NPD1548	Phase 1
0.7162	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1465	Phase 2
0.7151	Intermediate Similarity	NPD8313	Approved
0.7151	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD4287	Approved
0.7133	Intermediate Similarity	NPD4307	Phase 2
0.7126	Intermediate Similarity	NPD3926	Phase 2
0.7124	Intermediate Similarity	NPD6099	Approved
0.7124	Intermediate Similarity	NPD6100	Approved
0.7121	Intermediate Similarity	NPD846	Approved
0.7121	Intermediate Similarity	NPD940	Approved
0.7118	Intermediate Similarity	NPD1729	Discontinued
0.7117	Intermediate Similarity	NPD4288	Approved
0.7114	Intermediate Similarity	NPD411	Approved
0.7108	Intermediate Similarity	NPD1247	Approved
0.7108	Intermediate Similarity	NPD7199	Phase 2
0.7101	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7177	Discontinued
0.7086	Intermediate Similarity	NPD447	Suspended
0.7083	Intermediate Similarity	NPD1610	Phase 2
0.7081	Intermediate Similarity	NPD6585	Discontinued
0.7079	Intermediate Similarity	NPD4360	Phase 2
0.7079	Intermediate Similarity	NPD4363	Phase 3
0.7075	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3400	Discontinued
0.7047	Intermediate Similarity	NPD7008	Discontinued
0.7044	Intermediate Similarity	NPD5049	Phase 3
0.7044	Intermediate Similarity	NPD6273	Approved
0.7043	Intermediate Similarity	NPD8151	Discontinued
0.7039	Intermediate Similarity	NPD4361	Phase 2
0.7039	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1608	Approved
0.703	Intermediate Similarity	NPD6971	Discontinued
0.7024	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4477	Approved
0.7013	Intermediate Similarity	NPD4476	Approved
0.7012	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3887	Approved
0.7006	Intermediate Similarity	NPD2354	Approved
0.7	Intermediate Similarity	NPD1296	Phase 2
0.7	Intermediate Similarity	NPD5951	Approved
0.6994	Remote Similarity	NPD37	Approved
0.6993	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6234	Discontinued
0.6983	Remote Similarity	NPD6535	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