NPASS Compound

Structure

CID88141 OpenBabel06191715422D 23 24 0 0 0 0 0 0 0 0999 V2000 -8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -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 -9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 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 -6.9282 -1.0000 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 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 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 -9.5263 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 -6.0622 -1.5000 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 -10.3923 2.0000 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 -6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 14 2 0 0 0 0 2 8 2 0 0 0 0 2 14 1 0 0 0 0 3 9 1 0 0 0 0 3 15 2 0 0 0 0 4 10 2 0 0 0 0 4 15 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 12 1 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 19 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.12
Volume:	331.5
LogP:	2.475
LogD:	2.339
LogS:	-2.909
# Rotatable Bonds:	7
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.608
Synthetic Accessibility Score:	2.221
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.841
MDCK Permeability:	1.7140766431111842e-05
Pgp-inhibitor:	0.362
Pgp-substrate:	0.65
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	97.06897735595703%
Volume Distribution (VD):	0.469
Pgp-substrate:	1.7281843423843384%

ADMET: Metabolism

CYP1A2-inhibitor:	0.747
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.884
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.866
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.296
CYP2D6-substrate:	0.891
CYP3A4-inhibitor:	0.517
CYP3A4-substrate:	0.265

ADMET: Excretion

Clearance (CL):	17.117
Half-life (T1/2):	0.949

ADMET: Toxicity

hERG Blockers:	0.201
Human Hepatotoxicity (H-HT):	0.161
Drug-inuced Liver Injury (DILI):	0.548
AMES Toxicity:	0.418
Rat Oral Acute Toxicity:	0.606
Maximum Recommended Daily Dose:	0.577
Skin Sensitization:	0.947
Carcinogencity:	0.555
Eye Corrosion:	0.05
Eye Irritation:	0.95
Respiratory Toxicity:	0.698

Download Data

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

Natural Product: NPC88141

Natural Product ID:	NPC88141
*Common Name:**	1,7-Bis(4-Hydroxyphenyl)-1-Heptene-3,5-Dione
IUPAC Name:	(E)-1,7-bis(4-hydroxyphenyl)hept-1-ene-3,5-dione
Synonyms:
Standard InCHIKey:	AWUBJLRYWHOLFW-VZUCSPMQSA-N
Standard InCHI:	InChI=1S/C19H18O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-5,7-11,20-21H,6,12-13H2/b11-5+
SMILES:	O=C(CC(=O)/C=C/c1ccc(cc1)O)CCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489150
PubChem CID:	9796708
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

*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
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350137]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[12617587]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24124	Curcuma longa	Species	Zingiberaceae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	ED50	=	0.5	ug ml-1	PMID[529648]
NPT681	Cell Line	PC-12	Rattus norvegicus	ED50	=	1.0	ug ml-1	PMID[529648]

☑ 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 NPC88141 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	262
0.1-0.2	1497
0.2-0.3	4051
0.3-0.4	11327
0.4-0.5	7642
0.5-0.6	7522
0.6-0.7	8265
0.7-0.8	1929
0.8-0.85	146
0.85-0.9	36
0.9-0.95	14
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9703	High Similarity	NPC188677
0.9703	High Similarity	NPC69332
0.9703	High Similarity	NPC29989
0.9703	High Similarity	NPC70843
0.9703	High Similarity	NPC95178
0.9505	High Similarity	NPC120693
0.9505	High Similarity	NPC261573
0.9505	High Similarity	NPC8931
0.9406	High Similarity	NPC68269
0.9346	High Similarity	NPC285350
0.9259	High Similarity	NPC23402
0.9151	High Similarity	NPC116842
0.9151	High Similarity	NPC21162
0.9109	High Similarity	NPC130193
0.9083	High Similarity	NPC322197
0.9065	High Similarity	NPC177576
0.9029	High Similarity	NPC135784
0.901	High Similarity	NPC201967
0.9	High Similarity	NPC299252
0.9	High Similarity	NPC61062
0.9	High Similarity	NPC277394
0.8972	High Similarity	NPC252544
0.8972	High Similarity	NPC321252
0.8972	High Similarity	NPC222905
0.8962	High Similarity	NPC17525
0.8879	High Similarity	NPC95172
0.8868	High Similarity	NPC141523
0.8839	High Similarity	NPC249435
0.8829	High Similarity	NPC19290
0.8824	High Similarity	NPC260000
0.8807	High Similarity	NPC286222
0.875	High Similarity	NPC472585
0.8738	High Similarity	NPC280869
0.8716	High Similarity	NPC268388
0.8713	High Similarity	NPC151715
0.8692	High Similarity	NPC226699
0.8661	High Similarity	NPC28951
0.8661	High Similarity	NPC325646
0.8636	High Similarity	NPC51698
0.8627	High Similarity	NPC26244
0.8621	High Similarity	NPC86900
0.8621	High Similarity	NPC68167
0.8611	High Similarity	NPC317305
0.8598	High Similarity	NPC6984
0.8559	High Similarity	NPC242136
0.8558	High Similarity	NPC245561
0.8545	High Similarity	NPC297657
0.8544	High Similarity	NPC473388
0.8534	High Similarity	NPC196976
0.8522	High Similarity	NPC159525
0.8522	High Similarity	NPC473136
0.8519	High Similarity	NPC228737
0.8515	High Similarity	NPC45040
0.8505	High Similarity	NPC13495
0.8496	Intermediate Similarity	NPC128249
0.8476	Intermediate Similarity	NPC52472
0.8455	Intermediate Similarity	NPC183700
0.8448	Intermediate Similarity	NPC248363
0.8435	Intermediate Similarity	NPC158222
0.8435	Intermediate Similarity	NPC182240
0.8431	Intermediate Similarity	NPC181709
0.8396	Intermediate Similarity	NPC91461
0.8396	Intermediate Similarity	NPC7686
0.8396	Intermediate Similarity	NPC40258
0.8381	Intermediate Similarity	NPC132078
0.8381	Intermediate Similarity	NPC216468
0.8381	Intermediate Similarity	NPC51333
0.8381	Intermediate Similarity	NPC78119
0.8378	Intermediate Similarity	NPC470355
0.8378	Intermediate Similarity	NPC114682
0.8378	Intermediate Similarity	NPC212718
0.8365	Intermediate Similarity	NPC82664
0.8365	Intermediate Similarity	NPC292730
0.8365	Intermediate Similarity	NPC132271
0.8365	Intermediate Similarity	NPC216520
0.8362	Intermediate Similarity	NPC265454
0.8362	Intermediate Similarity	NPC34634
0.835	Intermediate Similarity	NPC128062
0.8349	Intermediate Similarity	NPC34715
0.8348	Intermediate Similarity	NPC184527
0.8348	Intermediate Similarity	NPC471033
0.8348	Intermediate Similarity	NPC311091
0.8347	Intermediate Similarity	NPC221777
0.8305	Intermediate Similarity	NPC91478
0.8305	Intermediate Similarity	NPC139171
0.8305	Intermediate Similarity	NPC32032
0.8305	Intermediate Similarity	NPC133909
0.8304	Intermediate Similarity	NPC228988
0.8302	Intermediate Similarity	NPC213730
0.8291	Intermediate Similarity	NPC216216
0.8291	Intermediate Similarity	NPC98305
0.8291	Intermediate Similarity	NPC236520
0.8291	Intermediate Similarity	NPC294361
0.8279	Intermediate Similarity	NPC304622
0.8276	Intermediate Similarity	NPC195262
0.8276	Intermediate Similarity	NPC188814
0.8276	Intermediate Similarity	NPC264976
0.8273	Intermediate Similarity	NPC224584
0.8273	Intermediate Similarity	NPC31274
0.8269	Intermediate Similarity	NPC274678
0.8264	Intermediate Similarity	NPC100067
0.8264	Intermediate Similarity	NPC72158
0.8264	Intermediate Similarity	NPC30501
0.8264	Intermediate Similarity	NPC105157
0.8264	Intermediate Similarity	NPC190043
0.8264	Intermediate Similarity	NPC169250
0.8264	Intermediate Similarity	NPC162612
0.8264	Intermediate Similarity	NPC103356
0.8264	Intermediate Similarity	NPC266689
0.8264	Intermediate Similarity	NPC23126
0.8264	Intermediate Similarity	NPC98254
0.8235	Intermediate Similarity	NPC14141
0.823	Intermediate Similarity	NPC11824
0.822	Intermediate Similarity	NPC242895
0.822	Intermediate Similarity	NPC73532
0.822	Intermediate Similarity	NPC120545
0.822	Intermediate Similarity	NPC143427
0.822	Intermediate Similarity	NPC19174
0.822	Intermediate Similarity	NPC267552
0.822	Intermediate Similarity	NPC224273
0.822	Intermediate Similarity	NPC115159
0.822	Intermediate Similarity	NPC295034
0.822	Intermediate Similarity	NPC31936
0.822	Intermediate Similarity	NPC45438
0.822	Intermediate Similarity	NPC156139
0.8208	Intermediate Similarity	NPC92730
0.8198	Intermediate Similarity	NPC79543
0.8197	Intermediate Similarity	NPC473017
0.8197	Intermediate Similarity	NPC21305
0.819	Intermediate Similarity	NPC273282
0.819	Intermediate Similarity	NPC474890
0.819	Intermediate Similarity	NPC161943
0.819	Intermediate Similarity	NPC289201
0.8182	Intermediate Similarity	NPC267846
0.8182	Intermediate Similarity	NPC62952
0.8182	Intermediate Similarity	NPC260952
0.8173	Intermediate Similarity	NPC76938
0.8173	Intermediate Similarity	NPC32977
0.8173	Intermediate Similarity	NPC81010
0.8167	Intermediate Similarity	NPC474766
0.8167	Intermediate Similarity	NPC164014
0.8165	Intermediate Similarity	NPC243677
0.8165	Intermediate Similarity	NPC303141
0.8148	Intermediate Similarity	NPC470202
0.8148	Intermediate Similarity	NPC168829
0.8142	Intermediate Similarity	NPC231717
0.8142	Intermediate Similarity	NPC17693
0.8137	Intermediate Similarity	NPC242240
0.8137	Intermediate Similarity	NPC123273
0.8137	Intermediate Similarity	NPC318325
0.8137	Intermediate Similarity	NPC280347
0.8137	Intermediate Similarity	NPC177420
0.8136	Intermediate Similarity	NPC297186
0.813	Intermediate Similarity	NPC474998
0.8125	Intermediate Similarity	NPC63345
0.812	Intermediate Similarity	NPC258366
0.812	Intermediate Similarity	NPC473767
0.812	Intermediate Similarity	NPC473974
0.812	Intermediate Similarity	NPC79933
0.812	Intermediate Similarity	NPC31296
0.8115	Intermediate Similarity	NPC276466
0.8115	Intermediate Similarity	NPC123722
0.8115	Intermediate Similarity	NPC151167
0.8115	Intermediate Similarity	NPC123228
0.8115	Intermediate Similarity	NPC116513
0.8115	Intermediate Similarity	NPC5018
0.8113	Intermediate Similarity	NPC225464
0.8108	Intermediate Similarity	NPC206341
0.8103	Intermediate Similarity	NPC325295
0.8103	Intermediate Similarity	NPC76308
0.8103	Intermediate Similarity	NPC469954
0.8099	Intermediate Similarity	NPC137416
0.8095	Intermediate Similarity	NPC286006
0.8095	Intermediate Similarity	NPC32714
0.8087	Intermediate Similarity	NPC51345
0.8073	Intermediate Similarity	NPC288411
0.8067	Intermediate Similarity	NPC154696
0.8058	Intermediate Similarity	NPC55561
0.8053	Intermediate Similarity	NPC228609
0.8051	Intermediate Similarity	NPC318552
0.8051	Intermediate Similarity	NPC190501
0.8049	Intermediate Similarity	NPC96024
0.8039	Intermediate Similarity	NPC25493
0.8039	Intermediate Similarity	NPC113460
0.8036	Intermediate Similarity	NPC326187
0.8033	Intermediate Similarity	NPC303680
0.8033	Intermediate Similarity	NPC90128
0.8033	Intermediate Similarity	NPC179777
0.8033	Intermediate Similarity	NPC8745
0.8033	Intermediate Similarity	NPC84076
0.8033	Intermediate Similarity	NPC92207
0.8033	Intermediate Similarity	NPC127937
0.8018	Intermediate Similarity	NPC29883
0.8017	Intermediate Similarity	NPC89630
0.8017	Intermediate Similarity	NPC83718
0.8017	Intermediate Similarity	NPC231767
0.8017	Intermediate Similarity	NPC471925
0.8017	Intermediate Similarity	NPC471928
0.8017	Intermediate Similarity	NPC477453
0.8017	Intermediate Similarity	NPC13238

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 NPC88141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	968
0.2-0.3	1097
0.3-0.4	2581
0.4-0.5	2317
0.5-0.6	1339
0.6-0.7	497
0.7-0.8	85
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8627	High Similarity	NPD2859	Approved
0.8627	High Similarity	NPD2860	Approved
0.8529	High Similarity	NPD2934	Approved
0.8529	High Similarity	NPD2933	Approved
0.8381	Intermediate Similarity	NPD3020	Approved
0.8051	Intermediate Similarity	NPD2932	Approved
0.8051	Intermediate Similarity	NPD3019	Approved
0.8018	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD1237	Approved
0.7876	Intermediate Similarity	NPD3021	Approved
0.7876	Intermediate Similarity	NPD3022	Approved
0.7851	Intermediate Similarity	NPD3972	Approved
0.783	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1164	Approved
0.7805	Intermediate Similarity	NPD1470	Approved
0.7787	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3764	Approved
0.7769	Intermediate Similarity	NPD1201	Approved
0.7712	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD943	Approved
0.7647	Intermediate Similarity	NPD111	Approved
0.7636	Intermediate Similarity	NPD3028	Approved
0.7632	Intermediate Similarity	NPD9266	Approved
0.7632	Intermediate Similarity	NPD74	Approved
0.7627	Intermediate Similarity	NPD255	Approved
0.7627	Intermediate Similarity	NPD256	Approved
0.7623	Intermediate Similarity	NPD1535	Discovery
0.7607	Intermediate Similarity	NPD1241	Discontinued
0.7583	Intermediate Similarity	NPD9545	Approved
0.7581	Intermediate Similarity	NPD1876	Approved
0.7568	Intermediate Similarity	NPD940	Approved
0.7568	Intermediate Similarity	NPD846	Approved
0.7561	Intermediate Similarity	NPD1481	Phase 2
0.7545	Intermediate Similarity	NPD2066	Phase 3
0.7544	Intermediate Similarity	NPD9267	Approved
0.7544	Intermediate Similarity	NPD9264	Approved
0.7544	Intermediate Similarity	NPD9263	Approved
0.7541	Intermediate Similarity	NPD3026	Approved
0.7541	Intermediate Similarity	NPD3847	Discontinued
0.7541	Intermediate Similarity	NPD3023	Approved
0.7521	Intermediate Similarity	NPD3025	Approved
0.7521	Intermediate Similarity	NPD3024	Approved
0.752	Intermediate Similarity	NPD2797	Approved
0.7519	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD3268	Approved
0.75	Intermediate Similarity	NPD5536	Phase 2
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7478	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1242	Phase 1
0.746	Intermediate Similarity	NPD2798	Approved
0.7444	Intermediate Similarity	NPD2344	Approved
0.7438	Intermediate Similarity	NPD1894	Discontinued
0.7431	Intermediate Similarity	NPD1809	Phase 2
0.7431	Intermediate Similarity	NPD844	Approved
0.7424	Intermediate Similarity	NPD1510	Phase 2
0.7424	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD2799	Discontinued
0.7417	Intermediate Similarity	NPD9493	Approved
0.7417	Intermediate Similarity	NPD9568	Approved
0.7407	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1202	Approved
0.7407	Intermediate Similarity	NPD845	Approved
0.7405	Intermediate Similarity	NPD1607	Approved
0.7381	Intermediate Similarity	NPD1203	Approved
0.7377	Intermediate Similarity	NPD1651	Approved
0.7368	Intermediate Similarity	NPD5408	Approved
0.7368	Intermediate Similarity	NPD5404	Approved
0.7368	Intermediate Similarity	NPD5405	Approved
0.7368	Intermediate Similarity	NPD5406	Approved
0.7345	Intermediate Similarity	NPD1930	Approved
0.7345	Intermediate Similarity	NPD1929	Approved
0.7345	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD2234	Approved
0.7311	Intermediate Similarity	NPD2229	Approved
0.7311	Intermediate Similarity	NPD2228	Approved
0.7295	Intermediate Similarity	NPD1759	Phase 1
0.7293	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD9256	Approved
0.729	Intermediate Similarity	NPD9258	Approved
0.7281	Intermediate Similarity	NPD5909	Discontinued
0.7279	Intermediate Similarity	NPD8166	Discontinued
0.7279	Intermediate Similarity	NPD3750	Approved
0.7259	Intermediate Similarity	NPD1549	Phase 2
0.725	Intermediate Similarity	NPD5951	Approved
0.725	Intermediate Similarity	NPD9281	Approved
0.7231	Intermediate Similarity	NPD2313	Discontinued
0.7231	Intermediate Similarity	NPD6798	Discontinued
0.7227	Intermediate Similarity	NPD5535	Approved
0.7226	Intermediate Similarity	NPD2309	Approved
0.7222	Intermediate Similarity	NPD1755	Approved
0.7213	Intermediate Similarity	NPD1758	Phase 1
0.7207	Intermediate Similarity	NPD288	Approved
0.72	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD9261	Approved
0.7185	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6663	Approved
0.7168	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1283	Approved
0.7153	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD4878	Approved
0.7132	Intermediate Similarity	NPD5736	Approved
0.7109	Intermediate Similarity	NPD3266	Approved
0.7109	Intermediate Similarity	NPD3267	Approved
0.7105	Intermediate Similarity	NPD1932	Approved
0.7099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD2342	Discontinued
0.7083	Intermediate Similarity	NPD7635	Approved
0.7077	Intermediate Similarity	NPD2614	Approved
0.7071	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6355	Discontinued
0.7064	Intermediate Similarity	NPD1239	Approved
0.7054	Intermediate Similarity	NPD257	Approved
0.7054	Intermediate Similarity	NPD258	Approved
0.7045	Intermediate Similarity	NPD6233	Phase 2
0.7045	Intermediate Similarity	NPD4062	Phase 3
0.704	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4308	Phase 3
0.7031	Intermediate Similarity	NPD3225	Approved
0.7029	Intermediate Similarity	NPD7003	Approved
0.7016	Intermediate Similarity	NPD5304	Approved
0.7016	Intermediate Similarity	NPD3091	Approved
0.7016	Intermediate Similarity	NPD5303	Approved
0.7009	Intermediate Similarity	NPD968	Approved
0.7009	Intermediate Similarity	NPD3134	Approved
0.7008	Intermediate Similarity	NPD1608	Approved
0.7008	Intermediate Similarity	NPD9269	Phase 2
0.7008	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD4208	Discontinued
0.7	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7390	Discontinued
0.6991	Remote Similarity	NPD9495	Approved
0.6985	Remote Similarity	NPD7450	Phase 2
0.6983	Remote Similarity	NPD9608	Approved
0.6983	Remote Similarity	NPD9610	Approved
0.6978	Remote Similarity	NPD6190	Approved
0.6978	Remote Similarity	NPD2354	Approved
0.6975	Remote Similarity	NPD5451	Approved
0.6975	Remote Similarity	NPD4750	Phase 3
0.6975	Remote Similarity	NPD1792	Phase 2
0.6967	Remote Similarity	NPD690	Clinical (unspecified phase)
0.696	Remote Similarity	NPD9268	Approved
0.696	Remote Similarity	NPD4093	Discontinued
0.6953	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5157	Phase 1
0.6953	Remote Similarity	NPD5159	Phase 2
0.6953	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD9491	Approved
0.6949	Remote Similarity	NPD1358	Approved
0.6947	Remote Similarity	NPD6832	Phase 2
0.6944	Remote Similarity	NPD4380	Phase 2
0.693	Remote Similarity	NPD1238	Approved
0.6929	Remote Similarity	NPD7440	Discontinued
0.6929	Remote Similarity	NPD1281	Approved
0.6923	Remote Similarity	NPD942	Approved
0.6916	Remote Similarity	NPD9257	Approved
0.6916	Remote Similarity	NPD9259	Approved
0.6912	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3748	Approved
0.6906	Remote Similarity	NPD3400	Discontinued
0.6905	Remote Similarity	NPD4626	Approved
0.6905	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2286	Discontinued
0.6905	Remote Similarity	NPD4589	Approved
0.6905	Remote Similarity	NPD4059	Approved
0.6897	Remote Similarity	NPD6647	Phase 2
0.6894	Remote Similarity	NPD7095	Approved
0.6891	Remote Similarity	NPD2684	Approved
0.6885	Remote Similarity	NPD5283	Phase 1
0.6885	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD800	Approved
0.6879	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1693	Approved
0.6875	Remote Similarity	NPD7458	Discontinued
0.6875	Remote Similarity	NPD688	Clinical (unspecified phase)
0.687	Remote Similarity	NPD9569	Approved
0.687	Remote Similarity	NPD9494	Approved
0.6866	Remote Similarity	NPD825	Approved
0.6866	Remote Similarity	NPD826	Approved
0.6864	Remote Similarity	NPD1444	Approved
0.6864	Remote Similarity	NPD1445	Approved
0.6861	Remote Similarity	NPD2796	Approved
0.6852	Remote Similarity	NPD4793	Discontinued
0.6846	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2629	Approved
0.6829	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6582	Phase 2
0.6822	Remote Similarity	NPD6583	Phase 3
0.6822	Remote Similarity	NPD4659	Approved
0.6818	Remote Similarity	NPD1086	Approved
0.6818	Remote Similarity	NPD1089	Approved
0.6818	Remote Similarity	NPD1090	Approved
0.6818	Remote Similarity	NPD4207	Discontinued
0.6812	Remote Similarity	NPD2353	Approved
0.6812	Remote Similarity	NPD2346	Discontinued

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