NPASS Compound

Structure

CID123228 OpenBabel06191715482D 24 25 0 0 0 0 0 0 0 0999 V2000 0.8660 -1.5000 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 -6.0622 -0.5000 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 -5.1962 0.0000 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 1.0000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 0.0000 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 -3.4641 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 1.0000 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 0.0000 0.0000 0.0000 C 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 -11.2583 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 15 1 0 0 0 0 5 17 1 0 0 0 0 6 10 1 0 0 0 0 6 15 2 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 13 19 1 0 0 0 0 14 16 2 0 0 0 0 14 20 1 0 0 0 0 17 21 2 0 0 0 0 18 22 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.15
Volume:	351.432
LogP:	3.101
LogD:	3.351
LogS:	-3.743
# Rotatable Bonds:	8
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.724
Synthetic Accessibility Score:	2.256
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.834
MDCK Permeability:	1.778179830580484e-05
Pgp-inhibitor:	0.697
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.125
30% Bioavailability (F30%):	0.373

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	98.67089080810547%
Volume Distribution (VD):	0.606
Pgp-substrate:	0.8210806250572205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.929
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.943
CYP2C19-substrate:	0.126
CYP2C9-inhibitor:	0.879
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.922
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.858
CYP3A4-substrate:	0.39

ADMET: Excretion

Clearance (CL):	15.132
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.293
Human Hepatotoxicity (H-HT):	0.359
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.96
Carcinogencity:	0.641
Eye Corrosion:	0.082
Eye Irritation:	0.956
Respiratory Toxicity:	0.885

Download Data

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

Natural Product: NPC123228

Natural Product ID:	NPC123228
*Common Name:**	1-(4-Hydroxy-3-Methoxyphenyl)-7-(4-Hydroxyphenyl)Hept-4-En-3-One
IUPAC Name:	(E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hept-4-en-3-one
Synonyms:
Standard InCHIKey:	JYHZFCAVESZNKO-HWKANZROSA-N
Standard InCHI:	InChI=1S/C20H22O4/c1-24-20-14-16(9-13-19(20)23)8-12-17(21)5-3-2-4-15-6-10-18(22)11-7-15/h3,5-7,9-11,13-14,22-23H,2,4,8,12H2,1H3/b5-3+
SMILES:	COc1cc(CCC(=O)/C=C/CCc2ccc(cc2)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1270357
PubChem CID:	5317593
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	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
NPO20553	NPC123228	Raw	Rhizome	1.42	1.42	1.42	mg/100g	Database [DUKE]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	2690.0	nM	PMID[533020]

☑ 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 NPC123228 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	289
0.1-0.2	1413
0.2-0.3	3997
0.3-0.4	10578
0.4-0.5	7556
0.5-0.6	3961
0.6-0.7	8364
0.7-0.8	5778
0.8-0.85	524
0.85-0.9	154
0.9-0.95	61
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC276466
1.0	High Similarity	NPC5018
1.0	High Similarity	NPC151167
1.0	High Similarity	NPC123722
0.9917	High Similarity	NPC84076
0.9917	High Similarity	NPC303680
0.9917	High Similarity	NPC90128
0.9917	High Similarity	NPC179777
0.9836	High Similarity	NPC304622
0.9669	High Similarity	NPC257589
0.9669	High Similarity	NPC53305
0.9667	High Similarity	NPC164778
0.9667	High Similarity	NPC257976
0.9667	High Similarity	NPC242372
0.9667	High Similarity	NPC4181
0.959	High Similarity	NPC92207
0.959	High Similarity	NPC276014
0.959	High Similarity	NPC127937
0.9587	High Similarity	NPC312404
0.9587	High Similarity	NPC273686
0.9583	High Similarity	NPC114298
0.9504	High Similarity	NPC229084
0.9504	High Similarity	NPC106659
0.9504	High Similarity	NPC160900
0.9504	High Similarity	NPC18984
0.944	High Similarity	NPC66905
0.944	High Similarity	NPC172673
0.9435	High Similarity	NPC226661
0.9417	High Similarity	NPC224814
0.9417	High Similarity	NPC269843
0.9417	High Similarity	NPC189844
0.9417	High Similarity	NPC60962
0.9417	High Similarity	NPC14007
0.9417	High Similarity	NPC158949
0.9417	High Similarity	NPC109083
0.9344	High Similarity	NPC163083
0.9339	High Similarity	NPC201777
0.9291	High Similarity	NPC239302
0.9286	High Similarity	NPC65935
0.9286	High Similarity	NPC319282
0.9286	High Similarity	NPC275724
0.9286	High Similarity	NPC215941
0.9286	High Similarity	NPC137427
0.9286	High Similarity	NPC244246
0.9286	High Similarity	NPC123196
0.9286	High Similarity	NPC311419
0.9262	High Similarity	NPC286573
0.925	High Similarity	NPC299406
0.9219	High Similarity	NPC327410
0.9194	High Similarity	NPC3221
0.916	High Similarity	NPC284409
0.9154	High Similarity	NPC90431
0.912	High Similarity	NPC213552
0.912	High Similarity	NPC120225
0.9091	High Similarity	NPC474784
0.9083	High Similarity	NPC280001
0.9055	High Similarity	NPC241354
0.9048	High Similarity	NPC20287
0.9048	High Similarity	NPC12022
0.9048	High Similarity	NPC16651
0.9048	High Similarity	NPC293641
0.9048	High Similarity	NPC32163
0.9048	High Similarity	NPC20404
0.904	High Similarity	NPC289459
0.904	High Similarity	NPC280767
0.9024	High Similarity	NPC194416
0.9024	High Similarity	NPC177291
0.9008	High Similarity	NPC470626
0.9	High Similarity	NPC19290
0.9	High Similarity	NPC299252
0.9	High Similarity	NPC61062
0.9	High Similarity	NPC471110
0.9	High Similarity	NPC277394
0.8976	High Similarity	NPC278308
0.896	High Similarity	NPC246704
0.8955	High Similarity	NPC472410
0.8947	High Similarity	NPC288452
0.8947	High Similarity	NPC289690
0.8931	High Similarity	NPC204592
0.8931	High Similarity	NPC152209
0.8926	High Similarity	NPC185738
0.8926	High Similarity	NPC293619
0.8923	High Similarity	NPC475468
0.8906	High Similarity	NPC83062
0.8889	High Similarity	NPC169214
0.8889	High Similarity	NPC229218
0.8889	High Similarity	NPC176030
0.8889	High Similarity	NPC87113
0.8889	High Similarity	NPC141817
0.8889	High Similarity	NPC192597
0.8881	High Similarity	NPC82336
0.8881	High Similarity	NPC78987
0.8862	High Similarity	NPC95614
0.8862	High Similarity	NPC56214
0.8862	High Similarity	NPC232316
0.8862	High Similarity	NPC227217
0.8862	High Similarity	NPC117780
0.8862	High Similarity	NPC165133
0.8862	High Similarity	NPC242885
0.8855	High Similarity	NPC5310
0.8855	High Similarity	NPC300776
0.8855	High Similarity	NPC4982
0.8855	High Similarity	NPC176814
0.8855	High Similarity	NPC68779
0.8846	High Similarity	NPC50763
0.8828	High Similarity	NPC478215
0.8828	High Similarity	NPC110313
0.8824	High Similarity	NPC16353
0.8824	High Similarity	NPC239608
0.8824	High Similarity	NPC46880
0.8824	High Similarity	NPC46161
0.8815	High Similarity	NPC110419
0.881	High Similarity	NPC146886
0.881	High Similarity	NPC20443
0.881	High Similarity	NPC60517
0.8806	High Similarity	NPC322021
0.879	High Similarity	NPC207613
0.8788	High Similarity	NPC113295
0.878	High Similarity	NPC310338
0.878	High Similarity	NPC281298
0.8759	High Similarity	NPC207732
0.875	High Similarity	NPC312256
0.8741	High Similarity	NPC28398
0.873	High Similarity	NPC244876
0.872	High Similarity	NPC54872
0.872	High Similarity	NPC470212
0.872	High Similarity	NPC38996
0.872	High Similarity	NPC312675
0.872	High Similarity	NPC184651
0.872	High Similarity	NPC160380
0.872	High Similarity	NPC473853
0.872	High Similarity	NPC343720
0.872	High Similarity	NPC113865
0.872	High Similarity	NPC262156
0.872	High Similarity	NPC324571
0.8712	High Similarity	NPC144662
0.8699	High Similarity	NPC70744
0.8699	High Similarity	NPC107588
0.8699	High Similarity	NPC164706
0.8699	High Similarity	NPC205502
0.8699	High Similarity	NPC137537
0.8699	High Similarity	NPC272471
0.8696	High Similarity	NPC157133
0.8692	High Similarity	NPC142985
0.8692	High Similarity	NPC195292
0.8689	High Similarity	NPC268317
0.8686	High Similarity	NPC254659
0.8686	High Similarity	NPC50954
0.8651	High Similarity	NPC86900
0.8651	High Similarity	NPC85488
0.8647	High Similarity	NPC139519
0.864	High Similarity	NPC204466
0.864	High Similarity	NPC98305
0.8633	High Similarity	NPC165389
0.8626	High Similarity	NPC469480
0.8623	High Similarity	NPC91694
0.8623	High Similarity	NPC258671
0.8623	High Similarity	NPC53884
0.8623	High Similarity	NPC300603
0.8623	High Similarity	NPC142165
0.8618	High Similarity	NPC39793
0.8618	High Similarity	NPC86947
0.8605	High Similarity	NPC117237
0.8605	High Similarity	NPC281020
0.8605	High Similarity	NPC203719
0.8603	High Similarity	NPC326065
0.8603	High Similarity	NPC19158
0.8583	High Similarity	NPC31344
0.8583	High Similarity	NPC156840
0.8583	High Similarity	NPC317769
0.8583	High Similarity	NPC280704
0.8583	High Similarity	NPC257124
0.8583	High Similarity	NPC8547
0.8583	High Similarity	NPC173746
0.8583	High Similarity	NPC297657
0.8583	High Similarity	NPC471693
0.8582	High Similarity	NPC324929
0.8571	High Similarity	NPC135127
0.8571	High Similarity	NPC476387
0.8571	High Similarity	NPC70752
0.8571	High Similarity	NPC119060
0.8571	High Similarity	NPC249791
0.8571	High Similarity	NPC237594
0.8561	High Similarity	NPC9370
0.8561	High Similarity	NPC111888
0.8561	High Similarity	NPC287495
0.856	High Similarity	NPC202474
0.856	High Similarity	NPC2058
0.8551	High Similarity	NPC224884
0.8551	High Similarity	NPC160378
0.8551	High Similarity	NPC471417
0.8551	High Similarity	NPC209085
0.8551	High Similarity	NPC304956
0.8551	High Similarity	NPC119663
0.855	High Similarity	NPC477694
0.855	High Similarity	NPC477705
0.854	High Similarity	NPC472332
0.854	High Similarity	NPC472335
0.8516	High Similarity	NPC288945
0.8512	High Similarity	NPC51698

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 NPC123228 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	911
0.2-0.3	1406
0.3-0.4	2558
0.4-0.5	1980
0.5-0.6	1129
0.6-0.7	724
0.7-0.8	155
0.8-0.85	5
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9504	High Similarity	NPD4379	Clinical (unspecified phase)
0.8926	High Similarity	NPD5536	Phase 2
0.8605	High Similarity	NPD9494	Approved
0.8583	High Similarity	NPD228	Approved
0.8293	Intermediate Similarity	NPD5283	Phase 1
0.8195	Intermediate Similarity	NPD3027	Phase 3
0.8108	Intermediate Similarity	NPD3882	Suspended
0.8099	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD2801	Approved
0.8027	Intermediate Similarity	NPD1934	Approved
0.7986	Intermediate Similarity	NPD2935	Discontinued
0.7967	Intermediate Similarity	NPD3022	Approved
0.7967	Intermediate Similarity	NPD3021	Approved
0.7907	Intermediate Similarity	NPD1651	Approved
0.7887	Intermediate Similarity	NPD8166	Discontinued
0.7857	Intermediate Similarity	NPD1241	Discontinued
0.7852	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1511	Approved
0.7803	Intermediate Similarity	NPD3972	Approved
0.7762	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD4628	Phase 3
0.7762	Intermediate Similarity	NPD4110	Phase 3
0.774	Intermediate Similarity	NPD1512	Approved
0.7737	Intermediate Similarity	NPD6798	Discontinued
0.7708	Intermediate Similarity	NPD6190	Approved
0.7703	Intermediate Similarity	NPD3455	Phase 2
0.7698	Intermediate Similarity	NPD6355	Discontinued
0.7698	Intermediate Similarity	NPD447	Suspended
0.7687	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1876	Approved
0.7687	Intermediate Similarity	NPD1283	Approved
0.7681	Intermediate Similarity	NPD6233	Phase 2
0.7681	Intermediate Similarity	NPD4062	Phase 3
0.7664	Intermediate Similarity	NPD7095	Approved
0.7652	Intermediate Similarity	NPD3847	Discontinued
0.7651	Intermediate Similarity	NPD7028	Phase 2
0.7632	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6166	Phase 2
0.7628	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD4060	Phase 1
0.7626	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD943	Approved
0.7626	Intermediate Similarity	NPD3620	Phase 2
0.7626	Intermediate Similarity	NPD1240	Approved
0.7603	Intermediate Similarity	NPD4357	Discontinued
0.7594	Intermediate Similarity	NPD1535	Discovery
0.7591	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD2798	Approved
0.7571	Intermediate Similarity	NPD230	Phase 1
0.7566	Intermediate Similarity	NPD3817	Phase 2
0.7557	Intermediate Similarity	NPD1894	Discontinued
0.7554	Intermediate Similarity	NPD2674	Phase 3
0.7552	Intermediate Similarity	NPD7266	Discontinued
0.7537	Intermediate Similarity	NPD1481	Phase 2
0.7535	Intermediate Similarity	NPD1510	Phase 2
0.7535	Intermediate Similarity	NPD2799	Discontinued
0.7532	Intermediate Similarity	NPD3818	Discontinued
0.752	Intermediate Similarity	NPD1358	Approved
0.7518	Intermediate Similarity	NPD1607	Approved
0.7518	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1357	Approved
0.75	Intermediate Similarity	NPD1613	Approved
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD1558	Phase 1
0.7484	Intermediate Similarity	NPD7054	Approved
0.7482	Intermediate Similarity	NPD3268	Approved
0.7481	Intermediate Similarity	NPD2982	Phase 2
0.7481	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2983	Phase 2
0.7467	Intermediate Similarity	NPD824	Approved
0.7463	Intermediate Similarity	NPD1281	Approved
0.746	Intermediate Similarity	NPD2684	Approved
0.7448	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1933	Approved
0.7444	Intermediate Similarity	NPD4626	Approved
0.7438	Intermediate Similarity	NPD7074	Phase 3
0.7438	Intermediate Similarity	NPD7472	Approved
0.7431	Intermediate Similarity	NPD2344	Approved
0.7419	Intermediate Similarity	NPD6234	Discontinued
0.7417	Intermediate Similarity	NPD4380	Phase 2
0.7407	Intermediate Similarity	NPD2981	Phase 2
0.7407	Intermediate Similarity	NPD1608	Approved
0.7391	Intermediate Similarity	NPD3018	Phase 2
0.7389	Intermediate Similarity	NPD6232	Discontinued
0.7372	Intermediate Similarity	NPD1203	Approved
0.7368	Intermediate Similarity	NPD6873	Phase 2
0.7368	Intermediate Similarity	NPD6385	Approved
0.7368	Intermediate Similarity	NPD6386	Approved
0.7365	Intermediate Similarity	NPD6799	Approved
0.7364	Intermediate Similarity	NPD7843	Approved
0.7358	Intermediate Similarity	NPD7473	Discontinued
0.7357	Intermediate Similarity	NPD3145	Approved
0.7357	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD3144	Approved
0.7351	Intermediate Similarity	NPD7458	Discontinued
0.7347	Intermediate Similarity	NPD2354	Approved
0.7333	Intermediate Similarity	NPD9296	Approved
0.7333	Intermediate Similarity	NPD2934	Approved
0.7333	Intermediate Similarity	NPD2933	Approved
0.7329	Intermediate Similarity	NPD3060	Approved
0.7328	Intermediate Similarity	NPD7157	Approved
0.7325	Intermediate Similarity	NPD2821	Approved
0.732	Intermediate Similarity	NPD37	Approved
0.7315	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD2932	Approved
0.7313	Intermediate Similarity	NPD3019	Approved
0.7302	Intermediate Similarity	NPD3134	Approved
0.7293	Intermediate Similarity	NPD9545	Approved
0.7284	Intermediate Similarity	NPD6797	Phase 2
0.7279	Intermediate Similarity	NPD7003	Approved
0.7279	Intermediate Similarity	NPD3750	Approved
0.7273	Intermediate Similarity	NPD1465	Phase 2
0.7273	Intermediate Similarity	NPD2860	Approved
0.7273	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2859	Approved
0.726	Intermediate Similarity	NPD4534	Discontinued
0.726	Intermediate Similarity	NPD1549	Phase 2
0.7259	Intermediate Similarity	NPD3496	Discontinued
0.7256	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD826	Approved
0.7254	Intermediate Similarity	NPD2979	Phase 3
0.7254	Intermediate Similarity	NPD825	Approved
0.7244	Intermediate Similarity	NPD7075	Discontinued
0.7241	Intermediate Similarity	NPD2438	Suspended
0.7239	Intermediate Similarity	NPD7685	Pre-registration
0.7239	Intermediate Similarity	NPD5585	Approved
0.7239	Intermediate Similarity	NPD7251	Discontinued
0.7237	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD3020	Approved
0.7234	Intermediate Similarity	NPD5109	Approved
0.7234	Intermediate Similarity	NPD2313	Discontinued
0.7234	Intermediate Similarity	NPD5111	Phase 2
0.7234	Intermediate Similarity	NPD5110	Phase 2
0.7234	Intermediate Similarity	NPD3764	Approved
0.7231	Intermediate Similarity	NPD5535	Approved
0.723	Intermediate Similarity	NPD2309	Approved
0.7226	Intermediate Similarity	NPD5978	Approved
0.7226	Intermediate Similarity	NPD5977	Approved
0.7219	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD8127	Discontinued
0.7214	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6832	Phase 2
0.7214	Intermediate Similarity	NPD2614	Approved
0.7206	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3705	Approved
0.7197	Intermediate Similarity	NPD6671	Approved
0.7195	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7808	Phase 3
0.7194	Intermediate Similarity	NPD257	Approved
0.7194	Intermediate Similarity	NPD6584	Phase 3
0.7194	Intermediate Similarity	NPD258	Approved
0.7194	Intermediate Similarity	NPD5647	Approved
0.7192	Intermediate Similarity	NPD2346	Discontinued
0.7192	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD17	Approved
0.7183	Intermediate Similarity	NPD259	Phase 1
0.7179	Intermediate Similarity	NPD4967	Phase 2
0.7179	Intermediate Similarity	NPD4966	Approved
0.7179	Intermediate Similarity	NPD4965	Approved
0.7178	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2922	Phase 1
0.7172	Intermediate Similarity	NPD4308	Phase 3
0.7171	Intermediate Similarity	NPD1653	Approved
0.7165	Intermediate Similarity	NPD968	Approved
0.7161	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5844	Phase 1
0.7153	Intermediate Similarity	NPD6653	Approved
0.7153	Intermediate Similarity	NPD9269	Phase 2
0.7153	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD5049	Phase 3
0.7152	Intermediate Similarity	NPD5494	Approved
0.7152	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7143	Intermediate Similarity	NPD5958	Discontinued
0.7143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9493	Approved
0.7134	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5451	Approved
0.7123	Intermediate Similarity	NPD2796	Approved
0.7122	Intermediate Similarity	NPD3266	Approved
0.7122	Intermediate Similarity	NPD3267	Approved
0.7114	Intermediate Similarity	NPD3887	Approved
0.7113	Intermediate Similarity	NPD5718	Phase 2
0.7111	Intermediate Similarity	NPD5691	Approved
0.7107	Intermediate Similarity	NPD7199	Phase 2
0.7099	Intermediate Similarity	NPD7228	Approved
0.7095	Intermediate Similarity	NPD4162	Approved
0.7086	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD555	Phase 2
0.7083	Intermediate Similarity	NPD4340	Discontinued
0.7083	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6599	Discontinued
0.7075	Intermediate Similarity	NPD2353	Approved
0.7075	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7440	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