NPASS Compound

Structure

CID184651 OpenBabel06191715562D 27 28 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 1.7321 -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 2.5981 -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 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 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 2 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 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 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 26 1 0 0 0 0 2 27 1 0 0 0 0 3 7 1 0 0 0 0 3 14 1 0 0 0 0 4 8 1 0 0 0 0 4 15 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 14 2 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 16 22 1 1 0 0 0 17 23 1 6 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 19 21 2 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.19
Volume:	391.582
LogP:	2.465
LogD:	2.354
LogS:	-4.321
# Rotatable Bonds:	10
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.509
Synthetic Accessibility Score:	2.978
Fsp3:	0.429
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:	-5.2
MDCK Permeability:	4.377169716462959e-06
Pgp-inhibitor:	0.02
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.512
30% Bioavailability (F30%):	0.91

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166
Plasma Protein Binding (PPB):	94.49752044677734%
Volume Distribution (VD):	1.077
Pgp-substrate:	4.168914794921875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.694
CYP1A2-substrate:	0.937
CYP2C19-inhibitor:	0.689
CYP2C19-substrate:	0.723
CYP2C9-inhibitor:	0.746
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.677
CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.384
CYP3A4-substrate:	0.752

ADMET: Excretion

Clearance (CL):	14.228
Half-life (T1/2):	0.902

ADMET: Toxicity

hERG Blockers:	0.264
Human Hepatotoxicity (H-HT):	0.27
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.951
Carcinogencity:	0.093
Eye Corrosion:	0.034
Eye Irritation:	0.869
Respiratory Toxicity:	0.594

Download Data

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

Natural Product: NPC184651

Natural Product ID:	NPC184651
*Common Name:**	(3R,5R)-1,7-Bis(4-Hydroxy-3-Methoxyphenyl)Heptane-3,5-Diol
IUPAC Name:	(3R,5R)-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-diol
Synonyms:
Standard InCHIKey:	OELMAFBLFOKZJD-IAGOWNOFSA-N
Standard InCHI:	InChI=1S/C21H28O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h5-6,9-12,16-17,22-25H,3-4,7-8,13H2,1-2H3/t16-,17-/m1/s1
SMILES:	COc1cc(CC[C@H](C[C@@H](CCc2ccc(c(c2)OC)O)O)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514825
PubChem CID:	10883331
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
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	rhizomes	SiMao City, Yunnan Province, China	1996-OCT	PMID[11908966]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[12350150]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[16124773]
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]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20715765]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33253561]
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		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.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13332	Tacca chantrieri	Species	Taccaceae	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	5
Others	2

Activity Type	# Activity
Cell Line	3
Individual Protein	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	100.0	ug.mL-1	PMID[571578]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	>	100.0	ug.mL-1	PMID[571578]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[571579]
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	84.3	%	PMID[571581]
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	101.2	%	PMID[571581]
NPT1	Others	Radical scavenging activity		IC50	=	12.3	ug.mL-1	PMID[571578]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	48.7	ug.mL-1	PMID[571578]

☑ 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 NPC184651 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	317
0.1-0.2	1384
0.2-0.3	4465
0.3-0.4	12536
0.4-0.5	5692
0.5-0.6	5060
0.6-0.7	8579
0.7-0.8	3385
0.8-0.85	738
0.85-0.9	389
0.9-0.95	131
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC343720
1.0	High Similarity	NPC262156
1.0	High Similarity	NPC473853
1.0	High Similarity	NPC54872
1.0	High Similarity	NPC470212
1.0	High Similarity	NPC324571
1.0	High Similarity	NPC312675
1.0	High Similarity	NPC113865
0.9912	High Similarity	NPC207613
0.9737	High Similarity	NPC24474
0.9737	High Similarity	NPC311595
0.9658	High Similarity	NPC471693
0.9658	High Similarity	NPC280704
0.9649	High Similarity	NPC470626
0.9649	High Similarity	NPC474214
0.9573	High Similarity	NPC85488
0.9565	High Similarity	NPC474320
0.9561	High Similarity	NPC164386
0.9561	High Similarity	NPC293619
0.95	High Similarity	NPC118533
0.95	High Similarity	NPC165045
0.9496	High Similarity	NPC148627
0.9487	High Similarity	NPC290451
0.9487	High Similarity	NPC127389
0.9483	High Similarity	NPC56214
0.9483	High Similarity	NPC227217
0.9483	High Similarity	NPC232316
0.9483	High Similarity	NPC165133
0.9483	High Similarity	NPC95614
0.9483	High Similarity	NPC242885
0.9483	High Similarity	NPC117780
0.9421	High Similarity	NPC206615
0.9421	High Similarity	NPC474178
0.9421	High Similarity	NPC186843
0.9421	High Similarity	NPC252307
0.9421	High Similarity	NPC245826
0.9421	High Similarity	NPC470213
0.9421	High Similarity	NPC98631
0.9412	High Similarity	NPC293701
0.9412	High Similarity	NPC114901
0.9412	High Similarity	NPC48990
0.9397	High Similarity	NPC281298
0.9397	High Similarity	NPC310338
0.9344	High Similarity	NPC475875
0.9344	High Similarity	NPC212015
0.9344	High Similarity	NPC170844
0.9344	High Similarity	NPC476968
0.9339	High Similarity	NPC163332
0.9339	High Similarity	NPC41706
0.9339	High Similarity	NPC319625
0.9339	High Similarity	NPC292056
0.9339	High Similarity	NPC147821
0.9339	High Similarity	NPC183181
0.9339	High Similarity	NPC118787
0.9339	High Similarity	NPC5428
0.9339	High Similarity	NPC111247
0.9333	High Similarity	NPC194519
0.9328	High Similarity	NPC317769
0.9328	High Similarity	NPC31344
0.9322	High Similarity	NPC476343
0.9322	High Similarity	NPC160380
0.9322	High Similarity	NPC38996
0.931	High Similarity	NPC474040
0.9268	High Similarity	NPC241522
0.9268	High Similarity	NPC257582
0.9268	High Similarity	NPC64201
0.9268	High Similarity	NPC77040
0.9268	High Similarity	NPC42300
0.9268	High Similarity	NPC92164
0.9268	High Similarity	NPC242807
0.9268	High Similarity	NPC174495
0.9268	High Similarity	NPC145305
0.9268	High Similarity	NPC153739
0.9268	High Similarity	NPC187998
0.9256	High Similarity	NPC178284
0.9256	High Similarity	NPC58607
0.9256	High Similarity	NPC191037
0.9194	High Similarity	NPC277804
0.9194	High Similarity	NPC474017
0.9187	High Similarity	NPC5851
0.9187	High Similarity	NPC86030
0.9174	High Similarity	NPC203133
0.9174	High Similarity	NPC116907
0.9174	High Similarity	NPC193544
0.9174	High Similarity	NPC298757
0.9174	High Similarity	NPC251855
0.9174	High Similarity	NPC117214
0.9174	High Similarity	NPC57490
0.9174	High Similarity	NPC472093
0.9174	High Similarity	NPC17943
0.9174	High Similarity	NPC221077
0.9174	High Similarity	NPC208950
0.9174	High Similarity	NPC475169
0.9174	High Similarity	NPC233410
0.9167	High Similarity	NPC228922
0.9167	High Similarity	NPC197757
0.916	High Similarity	NPC470804
0.9153	High Similarity	NPC35071
0.9153	High Similarity	NPC177475
0.9153	High Similarity	NPC148615
0.9145	High Similarity	NPC255675
0.912	High Similarity	NPC253105
0.912	High Similarity	NPC201587
0.9113	High Similarity	NPC319282
0.9113	High Similarity	NPC472338
0.9113	High Similarity	NPC143483
0.9113	High Similarity	NPC65935
0.9113	High Similarity	NPC137427
0.9113	High Similarity	NPC311419
0.9113	High Similarity	NPC215941
0.9113	High Similarity	NPC275724
0.9113	High Similarity	NPC123196
0.9113	High Similarity	NPC244246
0.9106	High Similarity	NPC21867
0.9106	High Similarity	NPC470084
0.9106	High Similarity	NPC45774
0.9106	High Similarity	NPC11258
0.9106	High Similarity	NPC128208
0.9106	High Similarity	NPC129570
0.9106	High Similarity	NPC307050
0.9106	High Similarity	NPC277458
0.9106	High Similarity	NPC72529
0.9106	High Similarity	NPC282703
0.9106	High Similarity	NPC184733
0.9091	High Similarity	NPC94276
0.9091	High Similarity	NPC109822
0.9083	High Similarity	NPC71090
0.9083	High Similarity	NPC41562
0.9068	High Similarity	NPC181969
0.9068	High Similarity	NPC320987
0.9068	High Similarity	NPC135961
0.906	High Similarity	NPC86947
0.9048	High Similarity	NPC475840
0.904	High Similarity	NPC27843
0.904	High Similarity	NPC7171
0.904	High Similarity	NPC472597
0.904	High Similarity	NPC470095
0.904	High Similarity	NPC40432
0.904	High Similarity	NPC228346
0.904	High Similarity	NPC470096
0.904	High Similarity	NPC161557
0.904	High Similarity	NPC115207
0.904	High Similarity	NPC158079
0.9035	High Similarity	NPC257430
0.9035	High Similarity	NPC173746
0.9035	High Similarity	NPC257124
0.9035	High Similarity	NPC179002
0.9035	High Similarity	NPC187583
0.9035	High Similarity	NPC78918
0.9035	High Similarity	NPC8547
0.9035	High Similarity	NPC156840
0.9035	High Similarity	NPC139617
0.9024	High Similarity	NPC293054
0.9024	High Similarity	NPC246620
0.9024	High Similarity	NPC169474
0.9024	High Similarity	NPC282000
0.9024	High Similarity	NPC106511
0.9024	High Similarity	NPC124452
0.9024	High Similarity	NPC159968
0.9024	High Similarity	NPC324112
0.9024	High Similarity	NPC236791
0.9024	High Similarity	NPC127587
0.9024	High Similarity	NPC82679
0.9024	High Similarity	NPC74817
0.9016	High Similarity	NPC53305
0.9016	High Similarity	NPC257589
0.9016	High Similarity	NPC228771
0.9016	High Similarity	NPC9067
0.9016	High Similarity	NPC29008
0.9016	High Similarity	NPC266705
0.9008	High Similarity	NPC233526
0.9008	High Similarity	NPC282496
0.9008	High Similarity	NPC136319
0.8976	High Similarity	NPC287745
0.8976	High Similarity	NPC478085
0.8974	High Similarity	NPC221049
0.8968	High Similarity	NPC106739
0.8968	High Similarity	NPC184447
0.8968	High Similarity	NPC470752
0.8968	High Similarity	NPC181049
0.8968	High Similarity	NPC160991
0.8968	High Similarity	NPC35932
0.8968	High Similarity	NPC16208
0.8968	High Similarity	NPC4940
0.8968	High Similarity	NPC7903
0.8968	High Similarity	NPC207400
0.896	High Similarity	NPC181079
0.896	High Similarity	NPC173308
0.8952	High Similarity	NPC472968
0.8947	High Similarity	NPC137685
0.8947	High Similarity	NPC174096
0.8947	High Similarity	NPC120982
0.8947	High Similarity	NPC79793
0.8947	High Similarity	NPC147634
0.8947	High Similarity	NPC226401
0.8943	High Similarity	NPC44748
0.8943	High Similarity	NPC274356
0.8943	High Similarity	NPC92207
0.8943	High Similarity	NPC78974
0.8943	High Similarity	NPC214406

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 NPC184651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	854
0.2-0.3	1677
0.3-0.4	2655
0.4-0.5	1782
0.5-0.6	969
0.6-0.7	734
0.7-0.8	179
0.8-0.85	9
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9344	High Similarity	NPD3027	Phase 3
0.9035	High Similarity	NPD228	Approved
0.8879	High Similarity	NPD5283	Phase 1
0.8699	High Similarity	NPD4379	Clinical (unspecified phase)
0.8534	High Similarity	NPD3021	Approved
0.8534	High Similarity	NPD3022	Approved
0.8527	High Similarity	NPD3619	Clinical (unspecified phase)
0.8527	High Similarity	NPD1613	Approved
0.8527	High Similarity	NPD3620	Phase 2
0.8527	High Similarity	NPD1612	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD1357	Approved
0.8291	Intermediate Similarity	NPD2684	Approved
0.8217	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8167	Intermediate Similarity	NPD7843	Approved
0.814	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.813	Intermediate Similarity	NPD5536	Phase 2
0.8115	Intermediate Similarity	NPD7157	Approved
0.8029	Intermediate Similarity	NPD3060	Approved
0.797	Intermediate Similarity	NPD4060	Phase 1
0.7969	Intermediate Similarity	NPD2983	Phase 2
0.7969	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD2982	Phase 2
0.7899	Intermediate Similarity	NPD290	Approved
0.7895	Intermediate Similarity	NPD2674	Phase 3
0.7891	Intermediate Similarity	NPD2981	Phase 2
0.7863	Intermediate Similarity	NPD3018	Phase 2
0.7836	Intermediate Similarity	NPD1558	Phase 1
0.7807	Intermediate Similarity	NPD2859	Approved
0.7807	Intermediate Similarity	NPD2860	Approved
0.7795	Intermediate Similarity	NPD5846	Approved
0.7795	Intermediate Similarity	NPD6516	Phase 2
0.7786	Intermediate Similarity	NPD6584	Phase 3
0.7778	Intermediate Similarity	NPD291	Approved
0.777	Intermediate Similarity	NPD5177	Phase 3
0.777	Intermediate Similarity	NPD4162	Approved
0.7759	Intermediate Similarity	NPD3020	Approved
0.7754	Intermediate Similarity	NPD7266	Discontinued
0.7727	Intermediate Similarity	NPD9494	Approved
0.7727	Intermediate Similarity	NPD2861	Phase 2
0.7719	Intermediate Similarity	NPD2933	Approved
0.7719	Intermediate Similarity	NPD9296	Approved
0.7719	Intermediate Similarity	NPD2934	Approved
0.7687	Intermediate Similarity	NPD5109	Approved
0.7687	Intermediate Similarity	NPD5111	Phase 2
0.7687	Intermediate Similarity	NPD5110	Phase 2
0.7687	Intermediate Similarity	NPD3145	Approved
0.7687	Intermediate Similarity	NPD3144	Approved
0.768	Intermediate Similarity	NPD6671	Approved
0.7674	Intermediate Similarity	NPD3705	Approved
0.7669	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4908	Phase 1
0.7667	Intermediate Similarity	NPD968	Approved
0.7664	Intermediate Similarity	NPD4536	Approved
0.7664	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD4538	Approved
0.766	Intermediate Similarity	NPD5241	Discontinued
0.7643	Intermediate Similarity	NPD4237	Approved
0.7643	Intermediate Similarity	NPD4236	Phase 3
0.7623	Intermediate Similarity	NPD5451	Approved
0.7619	Intermediate Similarity	NPD1934	Approved
0.7612	Intermediate Similarity	NPD7095	Approved
0.7589	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6331	Phase 2
0.7589	Intermediate Similarity	NPD4110	Phase 3
0.7568	Intermediate Similarity	NPD2978	Approved
0.7568	Intermediate Similarity	NPD2977	Approved
0.7557	Intermediate Similarity	NPD6582	Phase 2
0.7557	Intermediate Similarity	NPD6583	Phase 3
0.7556	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6798	Discontinued
0.7538	Intermediate Similarity	NPD1610	Phase 2
0.7518	Intermediate Similarity	NPD3657	Discovery
0.7518	Intermediate Similarity	NPD6355	Discontinued
0.7518	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6674	Discontinued
0.7518	Intermediate Similarity	NPD5735	Approved
0.75	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2922	Phase 1
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD1548	Phase 1
0.7482	Intermediate Similarity	NPD5588	Approved
0.7482	Intermediate Similarity	NPD5960	Phase 3
0.7481	Intermediate Similarity	NPD2231	Phase 2
0.7481	Intermediate Similarity	NPD2235	Phase 2
0.7462	Intermediate Similarity	NPD3847	Discontinued
0.745	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD2238	Phase 2
0.7444	Intermediate Similarity	NPD3094	Phase 2
0.744	Intermediate Similarity	NPD5535	Approved
0.7431	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2161	Phase 2
0.7426	Intermediate Similarity	NPD5718	Phase 2
0.741	Intermediate Similarity	NPD6896	Approved
0.741	Intermediate Similarity	NPD6895	Approved
0.7405	Intermediate Similarity	NPD1091	Approved
0.7405	Intermediate Similarity	NPD3092	Approved
0.7385	Intermediate Similarity	NPD2668	Approved
0.7385	Intermediate Similarity	NPD4626	Approved
0.7385	Intermediate Similarity	NPD2667	Approved
0.7383	Intermediate Similarity	NPD37	Approved
0.7376	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4062	Phase 3
0.7368	Intermediate Similarity	NPD8651	Approved
0.7368	Intermediate Similarity	NPD6234	Discontinued
0.7364	Intermediate Similarity	NPD3091	Approved
0.7357	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6166	Phase 2
0.7351	Intermediate Similarity	NPD3882	Suspended
0.7348	Intermediate Similarity	NPD2233	Approved
0.7348	Intermediate Similarity	NPD2230	Approved
0.7348	Intermediate Similarity	NPD2232	Approved
0.7347	Intermediate Similarity	NPD1653	Approved
0.7343	Intermediate Similarity	NPD4628	Phase 3
0.7343	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4535	Phase 3
0.7338	Intermediate Similarity	NPD6653	Approved
0.7333	Intermediate Similarity	NPD2801	Approved
0.7329	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7526	Approved
0.7329	Intermediate Similarity	NPD52	Approved
0.7319	Intermediate Similarity	NPD4140	Approved
0.7319	Intermediate Similarity	NPD3062	Approved
0.7319	Intermediate Similarity	NPD3061	Approved
0.7319	Intermediate Similarity	NPD3059	Approved
0.7317	Intermediate Similarity	NPD1358	Approved
0.7308	Intermediate Similarity	NPD1651	Approved
0.7305	Intermediate Similarity	NPD2935	Discontinued
0.7302	Intermediate Similarity	NPD821	Approved
0.7297	Intermediate Similarity	NPD4005	Discontinued
0.7293	Intermediate Similarity	NPD5327	Phase 3
0.7293	Intermediate Similarity	NPD1669	Approved
0.7293	Intermediate Similarity	NPD3685	Discontinued
0.7292	Intermediate Similarity	NPD6190	Approved
0.7292	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4123	Phase 3
0.7259	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4624	Approved
0.7254	Intermediate Similarity	NPD3540	Phase 1
0.7254	Intermediate Similarity	NPD5763	Approved
0.7254	Intermediate Similarity	NPD5762	Approved
0.7252	Intermediate Similarity	NPD9384	Approved
0.7252	Intermediate Similarity	NPD9381	Approved
0.725	Intermediate Similarity	NPD1242	Phase 1
0.7241	Intermediate Similarity	NPD5058	Phase 3
0.7239	Intermediate Similarity	NPD1283	Approved
0.7237	Intermediate Similarity	NPD4965	Approved
0.7237	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4966	Approved
0.7237	Intermediate Similarity	NPD4967	Phase 2
0.7226	Intermediate Similarity	NPD4625	Phase 3
0.7219	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5314	Approved
0.7211	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3596	Phase 2
0.7203	Intermediate Similarity	NPD844	Approved
0.7203	Intermediate Similarity	NPD2424	Discontinued
0.7203	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD556	Approved
0.7197	Intermediate Similarity	NPD3496	Discontinued
0.7192	Intermediate Similarity	NPD4357	Discontinued
0.7192	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7041	Phase 2
0.719	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3055	Approved
0.7185	Intermediate Similarity	NPD3053	Approved
0.7183	Intermediate Similarity	NPD6032	Approved
0.7183	Intermediate Similarity	NPD3539	Phase 1
0.7183	Intermediate Similarity	NPD2438	Suspended
0.7176	Intermediate Similarity	NPD5691	Approved
0.7174	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2677	Approved
0.717	Intermediate Similarity	NPD7074	Phase 3
0.7165	Intermediate Similarity	NPD9377	Approved
0.7165	Intermediate Similarity	NPD9379	Approved
0.7164	Intermediate Similarity	NPD9622	Approved
0.7164	Intermediate Similarity	NPD4749	Approved
0.7152	Intermediate Similarity	NPD3818	Discontinued
0.7152	Intermediate Similarity	NPD7228	Approved
0.7152	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4678	Approved
0.7133	Intermediate Similarity	NPD1375	Discontinued
0.7133	Intermediate Similarity	NPD4675	Approved
0.7132	Intermediate Similarity	NPD3691	Phase 2
0.7132	Intermediate Similarity	NPD3690	Phase 2
0.7132	Intermediate Similarity	NPD709	Approved
0.7123	Intermediate Similarity	NPD7124	Phase 2
0.7121	Intermediate Similarity	NPD3095	Discontinued
0.7114	Intermediate Similarity	NPD3687	Approved
0.7114	Intermediate Similarity	NPD3686	Approved
0.7113	Intermediate Similarity	NPD2154	Approved
0.7113	Intermediate Similarity	NPD2155	Approved
0.7113	Intermediate Similarity	NPD4108	Discontinued
0.7113	Intermediate Similarity	NPD2156	Approved
0.7111	Intermediate Similarity	NPD5311	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