NPASS Compound

Structure

NPC474784 OpenBabel07101718302D 28 29 0 0 1 0 0 0 0 0999 V2000 10.3923 -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 6.9282 -2.0000 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 0.0000 -2.0000 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 8.6603 -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 8.6603 -2.0000 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 4.3301 -1.5000 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 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 5.1962 -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 9.5263 -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 -2.0000 0.0000 C 0 0 3 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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 28 1 0 0 0 0 3 6 2 0 0 0 0 3 13 1 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 14 19 1 0 0 0 0 15 22 2 0 0 0 0 16 23 2 0 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 18 21 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.14
Volume:	392.463
LogP:	1.711
LogD:	1.185
LogS:	-2.733
# Rotatable Bonds:	9
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	2.968
Fsp3:	0.238
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.056
MDCK Permeability:	1.3455920452543069e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.913
Human Intestinal Absorption (HIA):	0.269
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.242
Plasma Protein Binding (PPB):	94.22158813476562%
Volume Distribution (VD):	0.514
Pgp-substrate:	5.481666564941406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.78
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.199
CYP2C9-inhibitor:	0.424
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.804
CYP3A4-inhibitor:	0.229
CYP3A4-substrate:	0.479

ADMET: Excretion

Clearance (CL):	14.516
Half-life (T1/2):	0.936

ADMET: Toxicity

hERG Blockers:	0.136
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.548
AMES Toxicity:	0.162
Rat Oral Acute Toxicity:	0.69
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.921
Carcinogencity:	0.565
Eye Corrosion:	0.005
Eye Irritation:	0.447
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC474784

Natural Product ID:	NPC474784
*Common Name:**	1-Hydroxy-1,7-Bis(4-Hydroxy-3-Methoxyphenyl)-6-Heptene-3,5-Dione
IUPAC Name:	(E)-7-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-ene-3,5-dione
Synonyms:
Standard InCHIKey:	NKDVMZOMVJQUDC-ZZXKWVIFSA-N
Standard InCHI:	InChI=1S/C21H22O7/c1-27-20-9-13(4-7-17(20)24)3-6-15(22)11-16(23)12-19(26)14-5-8-18(25)21(10-14)28-2/h3-10,19,24-26H,11-12H2,1-2H3/b6-3+
SMILES:	COC1=C(C=CC(=C1)C=CC(=O)CC(=O)CC(C2=CC(=C(C=C2)O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482608
PubChem CID:	13888134
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	=	30.7	ug ml-1	PMID[501686]
NPT681	Cell Line	PC-12	Rattus norvegicus	ED50	=	44.3	ug ml-1	PMID[501686]

☑ 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 NPC474784 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	335
0.1-0.2	1278
0.2-0.3	3445
0.3-0.4	8420
0.4-0.5	10067
0.5-0.6	3582
0.6-0.7	6395
0.7-0.8	7875
0.8-0.85	1096
0.85-0.9	171
0.9-0.95	32
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9318	High Similarity	NPC65935
0.9318	High Similarity	NPC123196
0.9318	High Similarity	NPC137427
0.9318	High Similarity	NPC244246
0.9318	High Similarity	NPC311419
0.9318	High Similarity	NPC215941
0.9318	High Similarity	NPC319282
0.9318	High Similarity	NPC275724
0.9281	High Similarity	NPC239608
0.9281	High Similarity	NPC46161
0.9242	High Similarity	NPC304622
0.9173	High Similarity	NPC195292
0.9091	High Similarity	NPC276466
0.9091	High Similarity	NPC5018
0.9091	High Similarity	NPC123722
0.9091	High Similarity	NPC151167
0.9091	High Similarity	NPC293641
0.9091	High Similarity	NPC12022
0.9091	High Similarity	NPC20287
0.9091	High Similarity	NPC20404
0.9091	High Similarity	NPC123228
0.903	High Similarity	NPC142985
0.9023	High Similarity	NPC278308
0.9015	High Similarity	NPC92207
0.9015	High Similarity	NPC90128
0.9015	High Similarity	NPC303680
0.9015	High Similarity	NPC84076
0.9015	High Similarity	NPC127937
0.9015	High Similarity	NPC179777
0.8993	High Similarity	NPC322021
0.8963	High Similarity	NPC469480
0.8958	High Similarity	NPC474903
0.8939	High Similarity	NPC257589
0.8939	High Similarity	NPC53305
0.8921	High Similarity	NPC325625
0.8912	High Similarity	NPC25127
0.8897	High Similarity	NPC50763
0.8889	High Similarity	NPC66905
0.8881	High Similarity	NPC30890
0.8881	High Similarity	NPC9370
0.8881	High Similarity	NPC287495
0.8832	High Similarity	NPC327410
0.8819	High Similarity	NPC221383
0.8819	High Similarity	NPC299090
0.8819	High Similarity	NPC283081
0.8819	High Similarity	NPC143892
0.8788	High Similarity	NPC257976
0.8788	High Similarity	NPC242372
0.8788	High Similarity	NPC163083
0.8788	High Similarity	NPC164778
0.8788	High Similarity	NPC160900
0.8788	High Similarity	NPC4181
0.8788	High Similarity	NPC106659
0.8788	High Similarity	NPC229084
0.8788	High Similarity	NPC18984
0.8788	High Similarity	NPC244876
0.8786	High Similarity	NPC284409
0.8784	High Similarity	NPC287504
0.8776	High Similarity	NPC151425
0.8759	High Similarity	NPC1580
0.8759	High Similarity	NPC472969
0.875	High Similarity	NPC172673
0.8741	High Similarity	NPC473090
0.8741	High Similarity	NPC50954
0.8741	High Similarity	NPC226661
0.8741	High Similarity	NPC254659
0.8731	High Similarity	NPC276014
0.8723	High Similarity	NPC289690
0.8723	High Similarity	NPC288452
0.8722	High Similarity	NPC273686
0.8722	High Similarity	NPC312404
0.8716	High Similarity	NPC323626
0.8716	High Similarity	NPC324233
0.8716	High Similarity	NPC327225
0.8712	High Similarity	NPC114298
0.8712	High Similarity	NPC86900
0.8705	High Similarity	NPC139519
0.8705	High Similarity	NPC152209
0.8705	High Similarity	NPC470990
0.8699	High Similarity	NPC203747
0.8699	High Similarity	NPC194653
0.8699	High Similarity	NPC254702
0.8699	High Similarity	NPC80710
0.8699	High Similarity	NPC139364
0.8699	High Similarity	NPC98809
0.8699	High Similarity	NPC476394
0.869	High Similarity	NPC208507
0.869	High Similarity	NPC472333
0.8681	High Similarity	NPC258671
0.8681	High Similarity	NPC207732
0.8681	High Similarity	NPC469683
0.8681	High Similarity	NPC53884
0.8681	High Similarity	NPC142165
0.8667	High Similarity	NPC469474
0.8662	High Similarity	NPC100675
0.8658	High Similarity	NPC124714
0.8658	High Similarity	NPC18727
0.8649	High Similarity	NPC256406
0.8647	High Similarity	NPC471693
0.8643	High Similarity	NPC90431
0.8643	High Similarity	NPC324929
0.8639	High Similarity	NPC40290
0.8639	High Similarity	NPC200060
0.8639	High Similarity	NPC69430
0.8639	High Similarity	NPC195763
0.8639	High Similarity	NPC142876
0.8639	High Similarity	NPC139293
0.8639	High Similarity	NPC264289
0.8639	High Similarity	NPC333691
0.8639	High Similarity	NPC102003
0.8639	High Similarity	NPC264550
0.8639	High Similarity	NPC92722
0.8636	High Similarity	NPC201777
0.8633	High Similarity	NPC249791
0.8633	High Similarity	NPC471110
0.8633	High Similarity	NPC476387
0.8633	High Similarity	NPC119060
0.8633	High Similarity	NPC237594
0.8633	High Similarity	NPC135127
0.8633	High Similarity	NPC106406
0.863	High Similarity	NPC98009
0.8623	High Similarity	NPC239302
0.8621	High Similarity	NPC157133
0.8621	High Similarity	NPC98356
0.8618	High Similarity	NPC472902
0.8618	High Similarity	NPC472961
0.8618	High Similarity	NPC472962
0.8611	High Similarity	NPC16353
0.8611	High Similarity	NPC471417
0.8611	High Similarity	NPC119663
0.8611	High Similarity	NPC304956
0.8611	High Similarity	NPC469615
0.8609	High Similarity	NPC474055
0.8609	High Similarity	NPC472598
0.8609	High Similarity	NPC52530
0.8609	High Similarity	NPC291508
0.8601	High Similarity	NPC110419
0.8592	High Similarity	NPC4796
0.8591	High Similarity	NPC35763
0.8591	High Similarity	NPC100971
0.8591	High Similarity	NPC209487
0.8591	High Similarity	NPC216769
0.8591	High Similarity	NPC236637
0.8591	High Similarity	NPC100263
0.8591	High Similarity	NPC291802
0.8591	High Similarity	NPC245382
0.8591	High Similarity	NPC121522
0.8591	High Similarity	NPC302950
0.8591	High Similarity	NPC269451
0.8591	High Similarity	NPC181209
0.8591	High Similarity	NPC219582
0.8591	High Similarity	NPC131266
0.8581	High Similarity	NPC243891
0.8581	High Similarity	NPC472279
0.8581	High Similarity	NPC62354
0.8571	High Similarity	NPC131451
0.8571	High Similarity	NPC287395
0.8571	High Similarity	NPC183655
0.8571	High Similarity	NPC113295
0.8571	High Similarity	NPC15329
0.8562	High Similarity	NPC165389
0.8562	High Similarity	NPC476359
0.8562	High Similarity	NPC12377
0.8562	High Similarity	NPC476338
0.8561	High Similarity	NPC14007
0.8561	High Similarity	NPC207613
0.8561	High Similarity	NPC158949
0.8561	High Similarity	NPC269843
0.8561	High Similarity	NPC307006
0.8561	High Similarity	NPC189844
0.8561	High Similarity	NPC109083
0.8561	High Similarity	NPC129889
0.8561	High Similarity	NPC224814
0.8561	High Similarity	NPC98305
0.8561	High Similarity	NPC60962
0.8552	High Similarity	NPC275278
0.8552	High Similarity	NPC223185
0.8543	High Similarity	NPC13858
0.8543	High Similarity	NPC320825
0.8543	High Similarity	NPC326037
0.8543	High Similarity	NPC278778
0.8543	High Similarity	NPC291878
0.8543	High Similarity	NPC195796
0.8543	High Similarity	NPC35038
0.8542	High Similarity	NPC284556
0.8542	High Similarity	NPC192597
0.8542	High Similarity	NPC176030
0.8542	High Similarity	NPC229218
0.8542	High Similarity	NPC312256
0.8542	High Similarity	NPC141817
0.8542	High Similarity	NPC169214
0.8542	High Similarity	NPC301178
0.8533	High Similarity	NPC250557
0.8531	High Similarity	NPC82336
0.8531	High Similarity	NPC78987
0.8531	High Similarity	NPC326065
0.8529	High Similarity	NPC118533
0.8529	High Similarity	NPC16651
0.8529	High Similarity	NPC165045
0.8529	High Similarity	NPC32163

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 NPC474784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	828
0.2-0.3	1608
0.3-0.4	2539
0.4-0.5	2006
0.5-0.6	1071
0.6-0.7	660
0.7-0.8	134
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8788	High Similarity	NPD4379	Clinical (unspecified phase)
0.8591	High Similarity	NPD1934	Approved
0.8411	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8406	Intermediate Similarity	NPD3027	Phase 3
0.8301	Intermediate Similarity	NPD3882	Suspended
0.8289	Intermediate Similarity	NPD2801	Approved
0.828	Intermediate Similarity	NPD6166	Phase 2
0.828	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD9494	Approved
0.8258	Intermediate Similarity	NPD5536	Phase 2
0.8176	Intermediate Similarity	NPD3818	Discontinued
0.8095	Intermediate Similarity	NPD4628	Phase 3
0.8092	Intermediate Similarity	NPD4380	Phase 2
0.8075	Intermediate Similarity	NPD7074	Phase 3
0.8054	Intermediate Similarity	NPD1511	Approved
0.8054	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD6190	Approved
0.8012	Intermediate Similarity	NPD7054	Approved
0.7963	Intermediate Similarity	NPD7472	Approved
0.7949	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1512	Approved
0.7885	Intermediate Similarity	NPD3817	Phase 2
0.7877	Intermediate Similarity	NPD1510	Phase 2
0.7847	Intermediate Similarity	NPD943	Approved
0.7847	Intermediate Similarity	NPD1240	Approved
0.7823	Intermediate Similarity	NPD2935	Discontinued
0.7805	Intermediate Similarity	NPD6797	Phase 2
0.7803	Intermediate Similarity	NPD228	Approved
0.7785	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7251	Discontinued
0.774	Intermediate Similarity	NPD1607	Approved
0.7724	Intermediate Similarity	NPD1613	Approved
0.7724	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD1549	Phase 2
0.7711	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7808	Phase 3
0.7702	Intermediate Similarity	NPD6232	Discontinued
0.7688	Intermediate Similarity	NPD5494	Approved
0.7687	Intermediate Similarity	NPD5283	Phase 1
0.7673	Intermediate Similarity	NPD7075	Discontinued
0.7671	Intermediate Similarity	NPD230	Phase 1
0.7669	Intermediate Similarity	NPD7473	Discontinued
0.7662	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7266	Discontinued
0.7651	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3972	Approved
0.7595	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2796	Approved
0.7582	Intermediate Similarity	NPD6799	Approved
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7574	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7685	Pre-registration
0.7544	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2344	Approved
0.7532	Intermediate Similarity	NPD37	Approved
0.7532	Intermediate Similarity	NPD6801	Discontinued
0.7516	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD8166	Discontinued
0.7483	Intermediate Similarity	NPD3620	Phase 2
0.7483	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6385	Approved
0.7468	Intermediate Similarity	NPD6386	Approved
0.7466	Intermediate Similarity	NPD6798	Discontinued
0.7448	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD447	Suspended
0.7432	Intermediate Similarity	NPD6355	Discontinued
0.7423	Intermediate Similarity	NPD8127	Discontinued
0.7415	Intermediate Similarity	NPD6233	Phase 2
0.7405	Intermediate Similarity	NPD6599	Discontinued
0.74	Intermediate Similarity	NPD7033	Discontinued
0.7394	Intermediate Similarity	NPD1608	Approved
0.7391	Intermediate Similarity	NPD4966	Approved
0.7391	Intermediate Similarity	NPD4965	Approved
0.7391	Intermediate Similarity	NPD4967	Phase 2
0.7388	Intermediate Similarity	NPD3021	Approved
0.7388	Intermediate Similarity	NPD3022	Approved
0.7379	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7819	Suspended
0.7375	Intermediate Similarity	NPD1465	Phase 2
0.7365	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1651	Approved
0.7347	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3455	Phase 2
0.7338	Intermediate Similarity	NPD2309	Approved
0.7337	Intermediate Similarity	NPD6559	Discontinued
0.7333	Intermediate Similarity	NPD3926	Phase 2
0.7329	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5402	Approved
0.732	Intermediate Similarity	NPD3060	Approved
0.7317	Intermediate Similarity	NPD7199	Phase 2
0.731	Intermediate Similarity	NPD2798	Approved
0.7308	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7228	Approved
0.7305	Intermediate Similarity	NPD3751	Discontinued
0.7299	Intermediate Similarity	NPD1241	Discontinued
0.7297	Intermediate Similarity	NPD4062	Phase 3
0.7292	Intermediate Similarity	NPD1876	Approved
0.7286	Intermediate Similarity	NPD9545	Approved
0.7285	Intermediate Similarity	NPD2799	Discontinued
0.7285	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1653	Approved
0.7255	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7411	Suspended
0.7248	Intermediate Similarity	NPD4060	Phase 1
0.7244	Intermediate Similarity	NPD4357	Discontinued
0.7234	Intermediate Similarity	NPD1357	Approved
0.7233	Intermediate Similarity	NPD7458	Discontinued
0.7215	Intermediate Similarity	NPD5403	Approved
0.7212	Intermediate Similarity	NPD1247	Approved
0.7212	Intermediate Similarity	NPD6959	Discontinued
0.7203	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD919	Approved
0.7192	Intermediate Similarity	NPD5647	Approved
0.7188	Intermediate Similarity	NPD7028	Phase 2
0.7185	Intermediate Similarity	NPD2684	Approved
0.7183	Intermediate Similarity	NPD17	Approved
0.7172	Intermediate Similarity	NPD1283	Approved
0.7169	Intermediate Similarity	NPD3787	Discontinued
0.7162	Intermediate Similarity	NPD7095	Approved
0.7161	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD9269	Phase 2
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7143	Intermediate Similarity	NPD2861	Phase 2
0.7135	Intermediate Similarity	NPD7038	Approved
0.7135	Intermediate Similarity	NPD7039	Approved
0.7133	Intermediate Similarity	NPD3847	Discontinued
0.7133	Intermediate Similarity	NPD1558	Phase 1
0.7126	Intermediate Similarity	NPD5242	Approved
0.7126	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD824	Approved
0.7125	Intermediate Similarity	NPD3226	Approved
0.7115	Intermediate Similarity	NPD2354	Approved
0.7115	Intermediate Similarity	NPD3887	Approved
0.7114	Intermediate Similarity	NPD3268	Approved
0.7114	Intermediate Similarity	NPD2313	Discontinued
0.7103	Intermediate Similarity	NPD2983	Phase 2
0.7103	Intermediate Similarity	NPD2982	Phase 2
0.7101	Intermediate Similarity	NPD7843	Approved
0.7089	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2532	Approved
0.7089	Intermediate Similarity	NPD4661	Approved
0.7089	Intermediate Similarity	NPD5401	Approved
0.7089	Intermediate Similarity	NPD2534	Approved
0.7089	Intermediate Similarity	NPD4662	Approved
0.7089	Intermediate Similarity	NPD2533	Approved
0.7086	Intermediate Similarity	NPD1933	Approved
0.7083	Intermediate Similarity	NPD1535	Discovery
0.7083	Intermediate Similarity	NPD3705	Approved
0.7078	Intermediate Similarity	NPD2346	Discontinued
0.7071	Intermediate Similarity	NPD7157	Approved
0.7062	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2977	Approved
0.7055	Intermediate Similarity	NPD2978	Approved
0.7052	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3750	Approved
0.7044	Intermediate Similarity	NPD6273	Approved
0.7042	Intermediate Similarity	NPD1894	Discontinued
0.7039	Intermediate Similarity	NPD6651	Approved
0.7039	Intermediate Similarity	NPD6653	Approved
0.7034	Intermediate Similarity	NPD2981	Phase 2
0.7034	Intermediate Similarity	NPD1481	Phase 2
0.7032	Intermediate Similarity	NPD4534	Discontinued
0.7029	Intermediate Similarity	NPD8434	Phase 2
0.7027	Intermediate Similarity	NPD3018	Phase 2
0.702	Intermediate Similarity	NPD2979	Phase 3
0.7013	Intermediate Similarity	NPD2438	Suspended
0.7013	Intermediate Similarity	NPD9570	Approved
0.7013	Intermediate Similarity	NPD1551	Phase 2
0.7013	Intermediate Similarity	NPD6099	Approved
0.7013	Intermediate Similarity	NPD6100	Approved
0.7012	Intermediate Similarity	NPD5977	Approved
0.7012	Intermediate Similarity	NPD5353	Approved
0.7012	Intermediate Similarity	NPD5978	Approved
0.7007	Intermediate Similarity	NPD2797	Approved
0.7007	Intermediate Similarity	NPD1203	Approved
0.7007	Intermediate Similarity	NPD1470	Approved
0.7	Intermediate Similarity	NPD2163	Approved
0.7	Intermediate Similarity	NPD3764	Approved
0.6994	Remote Similarity	NPD6844	Discontinued
0.6993	Remote Similarity	NPD4536	Approved
0.6993	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4538	Approved
0.6987	Remote Similarity	NPD2800	Approved
0.6987	Remote Similarity	NPD4236	Phase 3
0.6987	Remote Similarity	NPD4237	Approved
0.6986	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1358	Approved
0.6982	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3146	Approved
0.698	Remote Similarity	NPD6832	Phase 2
0.6974	Remote Similarity	NPD1899	Clinical (unspecified phase)

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