NPASS Compound

Structure

NPC474320 OpenBabel07101718182D 29 30 0 0 1 0 0 0 0 0999 V2000 -9.5263 5.5000 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 -6.9282 6.0000 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 -6.0622 2.5000 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 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 -8.6603 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 4.0000 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 -6.9282 3.0000 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 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6603 4.0000 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 -7.7942 4.5000 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 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 4.5000 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 -7.7942 5.5000 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 26 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 9 1 0 0 0 0 5 16 1 0 0 0 0 6 10 1 0 0 0 0 6 17 1 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 12 2 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 20 1 0 0 0 0 12 21 1 0 0 0 0 13 16 2 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 23 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 18 24 1 1 0 0 0 19 25 1 6 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 21 23 2 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.22
Volume:	426.174
LogP:	2.786
LogD:	2.785
LogS:	-4.723
# Rotatable Bonds:	12
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.565
Synthetic Accessibility Score:	2.822
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.856
MDCK Permeability:	2.5694158466649242e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.301
Plasma Protein Binding (PPB):	86.36872100830078%
Volume Distribution (VD):	0.857
Pgp-substrate:	2.725193738937378%

ADMET: Metabolism

CYP1A2-inhibitor:	0.259
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.735
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.588
CYP2C9-substrate:	0.771
CYP2D6-inhibitor:	0.077
CYP2D6-substrate:	0.936
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	10.176
Half-life (T1/2):	0.812

ADMET: Toxicity

hERG Blockers:	0.709
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.311
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.946
Carcinogencity:	0.074
Eye Corrosion:	0.018
Eye Irritation:	0.142
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC474320

Natural Product ID:	NPC474320
*Common Name:**	(3R,5R)-1,7-Bis(3,4-Dimethoxyphenyl)Heptane-3,5-Diol
IUPAC Name:	(3R,5R)-1,7-bis(3,4-dimethoxyphenyl)heptane-3,5-diol
Synonyms:
Standard InCHIKey:	NLRQFTHYBLYLSS-RTBURBONSA-N
Standard InCHI:	InChI=1S/C23H32O6/c1-26-20-11-7-16(13-22(20)28-3)5-9-18(24)15-19(25)10-6-17-8-12-21(27-2)23(14-17)29-4/h7-8,11-14,18-19,24-25H,5-6,9-10,15H2,1-4H3/t18-,19-/m1/s1
SMILES:	COc1cc(CC[C@H](C[C@@H](CCc2ccc(c(c2)OC)OC)O)O)ccc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465203
PubChem CID:	10949483
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]
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]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	4.9	ug.mL-1	PMID[479342]
NPT924	Cell Line	HSC-2	Homo sapiens	IC50	=	6.6	ug.mL-1	PMID[479342]
NPT27	Others	Unspecified		IC50	=	174.0	ug.mL-1	PMID[479342]

☑ 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 NPC474320 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	285
0.1-0.2	1352
0.2-0.3	4275
0.3-0.4	12493
0.4-0.5	5911
0.5-0.6	5392
0.6-0.7	8877
0.7-0.8	3125
0.8-0.85	669
0.85-0.9	265
0.9-0.95	40
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.991	High Similarity	NPC474214
0.9565	High Similarity	NPC184651
0.9565	High Similarity	NPC470212
0.9565	High Similarity	NPC262156
0.9565	High Similarity	NPC343720
0.9565	High Similarity	NPC312675
0.9565	High Similarity	NPC473853
0.9565	High Similarity	NPC113865
0.9565	High Similarity	NPC324571
0.9565	High Similarity	NPC54872
0.9558	High Similarity	NPC474040
0.9478	High Similarity	NPC207613
0.9304	High Similarity	NPC311595
0.9304	High Similarity	NPC24474
0.9237	High Similarity	NPC280704
0.9237	High Similarity	NPC471693
0.9217	High Similarity	NPC470626
0.9211	High Similarity	NPC9341
0.9211	High Similarity	NPC81067
0.9189	High Similarity	NPC137685
0.9167	High Similarity	NPC206882
0.916	High Similarity	NPC293701
0.916	High Similarity	NPC48990
0.916	High Similarity	NPC114901
0.9153	High Similarity	NPC85488
0.9153	High Similarity	NPC71090
0.913	High Similarity	NPC164386
0.913	High Similarity	NPC293619
0.9115	High Similarity	NPC165106
0.9099	High Similarity	NPC474272
0.9091	High Similarity	NPC165045
0.9091	High Similarity	NPC118533
0.9091	High Similarity	NPC242032
0.9083	High Similarity	NPC148627
0.9068	High Similarity	NPC127389
0.9068	High Similarity	NPC290451
0.906	High Similarity	NPC242885
0.906	High Similarity	NPC227217
0.906	High Similarity	NPC165133
0.906	High Similarity	NPC56214
0.906	High Similarity	NPC232316
0.906	High Similarity	NPC117780
0.906	High Similarity	NPC95614
0.9016	High Similarity	NPC98631
0.9016	High Similarity	NPC470213
0.9016	High Similarity	NPC245826
0.9016	High Similarity	NPC186843
0.9016	High Similarity	NPC252307
0.9016	High Similarity	NPC474178
0.9016	High Similarity	NPC470084
0.9016	High Similarity	NPC206615
0.9	High Similarity	NPC94276
0.9	High Similarity	NPC109822
0.8974	High Similarity	NPC135961
0.8974	High Similarity	NPC310338
0.8974	High Similarity	NPC281298
0.8957	High Similarity	NPC473264
0.8957	High Similarity	NPC47194
0.8957	High Similarity	NPC475815
0.8943	High Similarity	NPC475875
0.8943	High Similarity	NPC476968
0.8943	High Similarity	NPC212015
0.8943	High Similarity	NPC469963
0.8943	High Similarity	NPC170844
0.8943	High Similarity	NPC469951
0.8934	High Similarity	NPC183181
0.8934	High Similarity	NPC163332
0.8934	High Similarity	NPC41706
0.8934	High Similarity	NPC147821
0.8934	High Similarity	NPC292056
0.8934	High Similarity	NPC5428
0.8934	High Similarity	NPC319625
0.8934	High Similarity	NPC111247
0.8934	High Similarity	NPC118787
0.8934	High Similarity	NPC474119
0.8926	High Similarity	NPC194519
0.8917	High Similarity	NPC317769
0.8917	High Similarity	NPC282496
0.8917	High Similarity	NPC233526
0.8917	High Similarity	NPC31344
0.8908	High Similarity	NPC38996
0.8908	High Similarity	NPC476343
0.8908	High Similarity	NPC160380
0.8871	High Similarity	NPC187998
0.8871	High Similarity	NPC77040
0.8871	High Similarity	NPC257582
0.8871	High Similarity	NPC174495
0.8871	High Similarity	NPC64201
0.8871	High Similarity	NPC153739
0.8871	High Similarity	NPC145305
0.8871	High Similarity	NPC92164
0.8871	High Similarity	NPC242807
0.8871	High Similarity	NPC241522
0.8871	High Similarity	NPC42300
0.8852	High Similarity	NPC178284
0.8852	High Similarity	NPC58607
0.8852	High Similarity	NPC191037
0.8814	High Similarity	NPC254625
0.8814	High Similarity	NPC475961
0.88	High Similarity	NPC30043
0.88	High Similarity	NPC469625
0.88	High Similarity	NPC469613
0.88	High Similarity	NPC470096
0.88	High Similarity	NPC474017
0.88	High Similarity	NPC277804
0.88	High Similarity	NPC470095
0.879	High Similarity	NPC470258
0.879	High Similarity	NPC273295
0.879	High Similarity	NPC202582
0.879	High Similarity	NPC3439
0.879	High Similarity	NPC222004
0.879	High Similarity	NPC285339
0.879	High Similarity	NPC226788
0.879	High Similarity	NPC218856
0.879	High Similarity	NPC190629
0.879	High Similarity	NPC86030
0.879	High Similarity	NPC5851
0.879	High Similarity	NPC210623
0.877	High Similarity	NPC233410
0.877	High Similarity	NPC203133
0.877	High Similarity	NPC472093
0.877	High Similarity	NPC105925
0.877	High Similarity	NPC193544
0.877	High Similarity	NPC57490
0.877	High Similarity	NPC117214
0.877	High Similarity	NPC208950
0.877	High Similarity	NPC298757
0.877	High Similarity	NPC116907
0.877	High Similarity	NPC221077
0.877	High Similarity	NPC251855
0.877	High Similarity	NPC17943
0.877	High Similarity	NPC475169
0.876	High Similarity	NPC197757
0.876	High Similarity	NPC244876
0.876	High Similarity	NPC228922
0.875	High Similarity	NPC312713
0.875	High Similarity	NPC126935
0.875	High Similarity	NPC470804
0.875	High Similarity	NPC65933
0.875	High Similarity	NPC172676
0.875	High Similarity	NPC227894
0.875	High Similarity	NPC216929
0.875	High Similarity	NPC57268
0.875	High Similarity	NPC477886
0.8739	High Similarity	NPC474565
0.8739	High Similarity	NPC177475
0.8739	High Similarity	NPC35071
0.8739	High Similarity	NPC148615
0.873	High Similarity	NPC253105
0.873	High Similarity	NPC201587
0.873	High Similarity	NPC470752
0.873	High Similarity	NPC230219
0.8729	High Similarity	NPC255675
0.8729	High Similarity	NPC63083
0.872	High Similarity	NPC472338
0.872	High Similarity	NPC244246
0.872	High Similarity	NPC311419
0.872	High Similarity	NPC469614
0.872	High Similarity	NPC469612
0.872	High Similarity	NPC123196
0.872	High Similarity	NPC143483
0.872	High Similarity	NPC65935
0.872	High Similarity	NPC215941
0.872	High Similarity	NPC319282
0.872	High Similarity	NPC137427
0.872	High Similarity	NPC275724
0.871	High Similarity	NPC128208
0.871	High Similarity	NPC307050
0.871	High Similarity	NPC277458
0.871	High Similarity	NPC11258
0.871	High Similarity	NPC21867
0.871	High Similarity	NPC72529
0.871	High Similarity	NPC282703
0.871	High Similarity	NPC184733
0.871	High Similarity	NPC45774
0.871	High Similarity	NPC129570
0.8699	High Similarity	NPC40352
0.8699	High Similarity	NPC213711
0.8696	High Similarity	NPC165646
0.8689	High Similarity	NPC18449
0.8689	High Similarity	NPC34902
0.8689	High Similarity	NPC121783
0.8678	High Similarity	NPC261661
0.8678	High Similarity	NPC41562
0.8678	High Similarity	NPC30462
0.8673	High Similarity	NPC75440
0.8667	High Similarity	NPC166759
0.8661	High Similarity	NPC475840
0.8661	High Similarity	NPC26394
0.8661	High Similarity	NPC263064
0.8655	High Similarity	NPC320987
0.8655	High Similarity	NPC181969
0.8651	High Similarity	NPC7171
0.8651	High Similarity	NPC309787
0.8651	High Similarity	NPC115207
0.8651	High Similarity	NPC472597
0.8651	High Similarity	NPC40432
0.8651	High Similarity	NPC158079
0.8651	High Similarity	NPC27843
0.8651	High Similarity	NPC161557

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 NPC474320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	881
0.2-0.3	1592
0.3-0.4	2610
0.4-0.5	1858
0.5-0.6	1013
0.6-0.7	724
0.7-0.8	205
0.8-0.85	12
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9115	High Similarity	NPD5283	Phase 1
0.8943	High Similarity	NPD3027	Phase 3
0.8609	High Similarity	NPD228	Approved
0.8376	Intermediate Similarity	NPD7843	Approved
0.8348	Intermediate Similarity	NPD2684	Approved
0.8347	Intermediate Similarity	NPD1357	Approved
0.8333	Intermediate Similarity	NPD5536	Phase 2
0.8319	Intermediate Similarity	NPD7157	Approved
0.8306	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD2982	Phase 2
0.816	Intermediate Similarity	NPD2983	Phase 2
0.8154	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD3620	Phase 2
0.8154	Intermediate Similarity	NPD1613	Approved
0.812	Intermediate Similarity	NPD3022	Approved
0.812	Intermediate Similarity	NPD3021	Approved
0.808	Intermediate Similarity	NPD2981	Phase 2
0.8047	Intermediate Similarity	NPD3018	Phase 2
0.7984	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD290	Approved
0.7941	Intermediate Similarity	NPD3060	Approved
0.7874	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD5109	Approved
0.7863	Intermediate Similarity	NPD5111	Phase 2
0.7863	Intermediate Similarity	NPD5110	Phase 2
0.7857	Intermediate Similarity	NPD3705	Approved
0.7846	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6516	Phase 2
0.784	Intermediate Similarity	NPD5846	Approved
0.7826	Intermediate Similarity	NPD291	Approved
0.7815	Intermediate Similarity	NPD5451	Approved
0.781	Intermediate Similarity	NPD4162	Approved
0.781	Intermediate Similarity	NPD4237	Approved
0.781	Intermediate Similarity	NPD5177	Phase 3
0.781	Intermediate Similarity	NPD4236	Phase 3
0.7786	Intermediate Similarity	NPD7095	Approved
0.7769	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD6331	Phase 2
0.7754	Intermediate Similarity	NPD4110	Phase 3
0.7754	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4060	Phase 1
0.7727	Intermediate Similarity	NPD5718	Phase 2
0.7724	Intermediate Similarity	NPD6671	Approved
0.7704	Intermediate Similarity	NPD4536	Approved
0.7704	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD6895	Approved
0.7704	Intermediate Similarity	NPD4538	Approved
0.7704	Intermediate Similarity	NPD6896	Approved
0.7699	Intermediate Similarity	NPD2859	Approved
0.7699	Intermediate Similarity	NPD2860	Approved
0.7698	Intermediate Similarity	NPD5241	Discontinued
0.7692	Intermediate Similarity	NPD6584	Phase 3
0.7687	Intermediate Similarity	NPD5735	Approved
0.7687	Intermediate Similarity	NPD6355	Discontinued
0.7687	Intermediate Similarity	NPD3657	Discovery
0.7681	Intermediate Similarity	NPD6674	Discontinued
0.7674	Intermediate Similarity	NPD2922	Phase 1
0.7669	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD3020	Approved
0.7638	Intermediate Similarity	NPD3847	Discontinued
0.7634	Intermediate Similarity	NPD2861	Phase 2
0.7626	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD5535	Approved
0.7611	Intermediate Similarity	NPD2933	Approved
0.7611	Intermediate Similarity	NPD2934	Approved
0.7606	Intermediate Similarity	NPD7526	Approved
0.7606	Intermediate Similarity	NPD52	Approved
0.7606	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5327	Phase 3
0.7594	Intermediate Similarity	NPD6798	Discontinued
0.7591	Intermediate Similarity	NPD2161	Phase 2
0.7576	Intermediate Similarity	NPD4908	Phase 1
0.7563	Intermediate Similarity	NPD968	Approved
0.7559	Intermediate Similarity	NPD2668	Approved
0.7559	Intermediate Similarity	NPD2667	Approved
0.7554	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD8651	Approved
0.7537	Intermediate Similarity	NPD2674	Phase 3
0.7537	Intermediate Similarity	NPD6233	Phase 2
0.7536	Intermediate Similarity	NPD7266	Discontinued
0.7519	Intermediate Similarity	NPD2231	Phase 2
0.7519	Intermediate Similarity	NPD2235	Phase 2
0.7518	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD5588	Approved
0.7518	Intermediate Similarity	NPD5960	Phase 3
0.75	Intermediate Similarity	NPD1358	Approved
0.7481	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2238	Phase 2
0.7481	Intermediate Similarity	NPD4140	Approved
0.7481	Intermediate Similarity	NPD1558	Phase 1
0.748	Intermediate Similarity	NPD1651	Approved
0.748	Intermediate Similarity	NPD821	Approved
0.7465	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD6582	Phase 2
0.7462	Intermediate Similarity	NPD6583	Phase 3
0.7462	Intermediate Similarity	NPD3685	Discontinued
0.7462	Intermediate Similarity	NPD1669	Approved
0.745	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4005	Discontinued
0.7447	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1610	Phase 2
0.7424	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD4624	Approved
0.7422	Intermediate Similarity	NPD4626	Approved
0.7415	Intermediate Similarity	NPD37	Approved
0.741	Intermediate Similarity	NPD3540	Phase 1
0.741	Intermediate Similarity	NPD5763	Approved
0.741	Intermediate Similarity	NPD5762	Approved
0.7407	Intermediate Similarity	NPD4062	Phase 3
0.7405	Intermediate Similarity	NPD1283	Approved
0.7402	Intermediate Similarity	NPD1548	Phase 1
0.7394	Intermediate Similarity	NPD7124	Phase 2
0.7385	Intermediate Similarity	NPD2233	Approved
0.7385	Intermediate Similarity	NPD2230	Approved
0.7385	Intermediate Similarity	NPD2232	Approved
0.7381	Intermediate Similarity	NPD3596	Phase 2
0.7376	Intermediate Similarity	NPD4535	Phase 3
0.7372	Intermediate Similarity	NPD6353	Approved
0.7372	Intermediate Similarity	NPD6653	Approved
0.7368	Intermediate Similarity	NPD9494	Approved
0.7365	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD7153	Discontinued
0.7357	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD5691	Approved
0.7338	Intermediate Similarity	NPD3539	Phase 1
0.7338	Intermediate Similarity	NPD2438	Suspended
0.7338	Intermediate Similarity	NPD6032	Approved
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3144	Approved
0.7333	Intermediate Similarity	NPD3145	Approved
0.7319	Intermediate Similarity	NPD7097	Phase 1
0.7315	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1091	Approved
0.7304	Intermediate Similarity	NPD9296	Approved
0.7302	Intermediate Similarity	NPD709	Approved
0.7297	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1934	Approved
0.7293	Intermediate Similarity	NPD3691	Phase 2
0.7293	Intermediate Similarity	NPD3690	Phase 2
0.7292	Intermediate Similarity	NPD4123	Phase 3
0.7287	Intermediate Similarity	NPD3095	Discontinued
0.7286	Intermediate Similarity	NPD1375	Discontinued
0.7273	Intermediate Similarity	NPD3134	Approved
0.7273	Intermediate Similarity	NPD5058	Phase 3
0.7273	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4965	Approved
0.7267	Intermediate Similarity	NPD4967	Phase 2
0.7267	Intermediate Similarity	NPD4966	Approved
0.7266	Intermediate Similarity	NPD6580	Approved
0.7266	Intermediate Similarity	NPD1182	Approved
0.7266	Intermediate Similarity	NPD4108	Discontinued
0.7266	Intermediate Similarity	NPD6581	Approved
0.7266	Intermediate Similarity	NPD3091	Approved
0.7266	Intermediate Similarity	NPD1894	Discontinued
0.7254	Intermediate Similarity	NPD4628	Phase 3
0.7248	Intermediate Similarity	NPD2977	Approved
0.7248	Intermediate Similarity	NPD2978	Approved
0.7236	Intermediate Similarity	NPD556	Approved
0.7234	Intermediate Similarity	NPD2424	Discontinued
0.7234	Intermediate Similarity	NPD2808	Discontinued
0.7231	Intermediate Similarity	NPD3496	Discontinued
0.7222	Intermediate Similarity	NPD4357	Discontinued
0.7222	Intermediate Similarity	NPD7041	Phase 2
0.7222	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3094	Phase 2
0.7214	Intermediate Similarity	NPD2935	Discontinued
0.7211	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5585	Approved
0.7206	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2677	Approved
0.7194	Intermediate Similarity	NPD6111	Discontinued
0.7176	Intermediate Similarity	NPD1281	Approved
0.7176	Intermediate Similarity	NPD3092	Approved
0.7165	Intermediate Similarity	NPD2557	Approved
0.7165	Intermediate Similarity	NPD6387	Discontinued
0.7164	Intermediate Similarity	NPD558	Phase 2
0.7162	Intermediate Similarity	NPD4678	Approved
0.7162	Intermediate Similarity	NPD4675	Approved
0.7155	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3531	Approved
0.7153	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3530	Approved
0.7153	Intermediate Similarity	NPD3532	Approved
0.7143	Intermediate Similarity	NPD3686	Approved
0.7143	Intermediate Similarity	NPD2156	Approved
0.7143	Intermediate Similarity	NPD3028	Approved
0.7143	Intermediate Similarity	NPD1242	Phase 1
0.7143	Intermediate Similarity	NPD2155	Approved
0.7143	Intermediate Similarity	NPD3687	Approved
0.7143	Intermediate Similarity	NPD2154	Approved
0.7133	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5772	Approved
0.7133	Intermediate Similarity	NPD5773	Approved
0.7132	Intermediate Similarity	NPD2669	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