NPASS Compound

Structure

NPC302681 OpenBabel07101718232D 30 31 0 0 0 0 0 0 0 0999 V2000 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 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 0.0000 -3.0000 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 -0.8660 -2.5000 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 9.5263 -4.5000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 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 8.6603 -4.0000 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 9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -4.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 2 1 0 0 0 0 1 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 21 1 0 0 0 0 16 24 2 0 0 0 0 17 22 2 0 0 0 0 17 25 1 0 0 0 0 18 22 1 0 0 0 0 18 26 2 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.26
Volume:	457.845
LogP:	6.141
LogD:	4.456
LogS:	-2.793
# Rotatable Bonds:	14
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.204
Synthetic Accessibility Score:	2.414
Fsp3:	0.462
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:	-5.158
MDCK Permeability:	2.516787026252132e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.069
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	99.73111724853516%
Volume Distribution (VD):	1.973
Pgp-substrate:	0.9151736497879028%

ADMET: Metabolism

CYP1A2-inhibitor:	0.887
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.948
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.479
CYP2C9-substrate:	0.993
CYP2D6-inhibitor:	0.983
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.644
CYP3A4-substrate:	0.081

ADMET: Excretion

Clearance (CL):	8.346
Half-life (T1/2):	0.948

ADMET: Toxicity

hERG Blockers:	0.373
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.009
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.982
Carcinogencity:	0.023
Eye Corrosion:	0.307
Eye Irritation:	0.957
Respiratory Toxicity:	0.412

Download Data

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

Natural Product: NPC302681

Natural Product ID:	NPC302681
*Common Name:**	5-[(Z)-14-(3,5-Dihydroxyphenyl)Tetradec-8-Enyl]Benzene-1,3-Diol
IUPAC Name:	5-[(Z)-14-(3,5-dihydroxyphenyl)tetradec-8-enyl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	INRCFVYVWPWZJS-IWQZZHSRSA-N
Standard InCHI:	InChI=1S/C26H36O4/c27-23-15-21(16-24(28)19-23)13-11-9-7-5-3-1-2-4-6-8-10-12-14-22-17-25(29)20-26(30)18-22/h1,3,15-20,27-30H,2,4-14H2/b3-1-
SMILES:	Oc1cc(CCCCCCC/C=CCCCCCc2cc(O)cc(c2)O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465325
PubChem CID:	10525745
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO33313	oncostemon bojerianum	Species	n.a.	n.a.	leaves	Madagascar rainforest	n.a.	PMID[12444688]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	9.8	ug.mL-1	PMID[460910]

☑ 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 NPC302681 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	297
0.1-0.2	1609
0.2-0.3	4800
0.3-0.4	14202
0.4-0.5	4831
0.5-0.6	7833
0.6-0.7	6855
0.7-0.8	1902
0.8-0.85	217
0.85-0.9	82
0.9-0.95	56
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470700
1.0	High Similarity	NPC109691
1.0	High Similarity	NPC118286
1.0	High Similarity	NPC39097
1.0	High Similarity	NPC39664
0.9899	High Similarity	NPC54844
0.9898	High Similarity	NPC134829
0.9898	High Similarity	NPC246056
0.9796	High Similarity	NPC241891
0.9592	High Similarity	NPC72947
0.9592	High Similarity	NPC100340
0.9592	High Similarity	NPC143659
0.9592	High Similarity	NPC284011
0.9495	High Similarity	NPC168303
0.9495	High Similarity	NPC24404
0.9495	High Similarity	NPC242342
0.9495	High Similarity	NPC146798
0.9495	High Similarity	NPC85479
0.9495	High Similarity	NPC302219
0.9495	High Similarity	NPC313030
0.9495	High Similarity	NPC222522
0.9495	High Similarity	NPC249828
0.9495	High Similarity	NPC71002
0.9495	High Similarity	NPC106396
0.9495	High Similarity	NPC53051
0.9495	High Similarity	NPC94351
0.949	High Similarity	NPC10588
0.94	High Similarity	NPC30506
0.94	High Similarity	NPC102216
0.9394	High Similarity	NPC147310
0.9394	High Similarity	NPC11280
0.9394	High Similarity	NPC24407
0.9394	High Similarity	NPC294186
0.9394	High Similarity	NPC192032
0.9394	High Similarity	NPC166313
0.9394	High Similarity	NPC137415
0.932	High Similarity	NPC33728
0.932	High Similarity	NPC19808
0.9293	High Similarity	NPC166761
0.9286	High Similarity	NPC291789
0.9238	High Similarity	NPC166995
0.9238	High Similarity	NPC43525
0.9223	High Similarity	NPC174981
0.9151	High Similarity	NPC261343
0.9151	High Similarity	NPC23804
0.9143	High Similarity	NPC165770
0.9143	High Similarity	NPC476632
0.9143	High Similarity	NPC4493
0.9143	High Similarity	NPC225679
0.9143	High Similarity	NPC224527
0.9126	High Similarity	NPC232523
0.9126	High Similarity	NPC158253
0.9126	High Similarity	NPC305603
0.9126	High Similarity	NPC61033
0.9126	High Similarity	NPC204901
0.9118	High Similarity	NPC292452
0.9118	High Similarity	NPC474839
0.91	High Similarity	NPC248573
0.91	High Similarity	NPC275053
0.91	High Similarity	NPC161571
0.9082	High Similarity	NPC32714
0.9029	High Similarity	NPC201662
0.9029	High Similarity	NPC99836
0.9029	High Similarity	NPC12640
0.902	High Similarity	NPC119860
0.8991	High Similarity	NPC470760
0.8991	High Similarity	NPC15860
0.8991	High Similarity	NPC219070
0.8991	High Similarity	NPC470759
0.8991	High Similarity	NPC127894
0.898	High Similarity	NPC76938
0.8972	High Similarity	NPC117846
0.8962	High Similarity	NPC268032
0.8932	High Similarity	NPC37802
0.8899	High Similarity	NPC114064
0.8899	High Similarity	NPC115808
0.8889	High Similarity	NPC107240
0.8868	High Similarity	NPC475018
0.8857	High Similarity	NPC61885
0.8857	High Similarity	NPC63698
0.8846	High Similarity	NPC248904
0.8835	High Similarity	NPC218879
0.8835	High Similarity	NPC227458
0.8835	High Similarity	NPC244513
0.8807	High Similarity	NPC53906
0.8807	High Similarity	NPC84999
0.8807	High Similarity	NPC246760
0.8774	High Similarity	NPC186385
0.8774	High Similarity	NPC299568
0.8774	High Similarity	NPC202647
0.8739	High Similarity	NPC144343
0.8739	High Similarity	NPC9592
0.8739	High Similarity	NPC48781
0.8725	High Similarity	NPC294741
0.8716	High Similarity	NPC22610
0.8716	High Similarity	NPC276737
0.87	High Similarity	NPC274678
0.8687	High Similarity	NPC306884
0.8687	High Similarity	NPC295295
0.8687	High Similarity	NPC94139
0.8687	High Similarity	NPC147284
0.8687	High Similarity	NPC162314
0.8687	High Similarity	NPC210497
0.8687	High Similarity	NPC3358
0.8679	High Similarity	NPC105727
0.8679	High Similarity	NPC58427
0.8679	High Similarity	NPC114392
0.8679	High Similarity	NPC34864
0.8673	High Similarity	NPC24125
0.8673	High Similarity	NPC192
0.8661	High Similarity	NPC217174
0.8654	High Similarity	NPC323810
0.8649	High Similarity	NPC33270
0.8649	High Similarity	NPC277588
0.8649	High Similarity	NPC69261
0.8649	High Similarity	NPC474933
0.8636	High Similarity	NPC808
0.86	High Similarity	NPC151715
0.8596	High Similarity	NPC237667
0.8585	High Similarity	NPC176527
0.8584	High Similarity	NPC69006
0.8584	High Similarity	NPC223451
0.8571	High Similarity	NPC190514
0.8559	High Similarity	NPC141090
0.8559	High Similarity	NPC123559
0.8559	High Similarity	NPC150624
0.8558	High Similarity	NPC315022
0.8558	High Similarity	NPC168393
0.8515	High Similarity	NPC26244
0.8496	Intermediate Similarity	NPC184302
0.8496	Intermediate Similarity	NPC191866
0.8476	Intermediate Similarity	NPC315936
0.8468	Intermediate Similarity	NPC472893
0.8468	Intermediate Similarity	NPC167934
0.8462	Intermediate Similarity	NPC91461
0.8462	Intermediate Similarity	NPC7686
0.8462	Intermediate Similarity	NPC40258
0.8455	Intermediate Similarity	NPC62546
0.8455	Intermediate Similarity	NPC263753
0.8455	Intermediate Similarity	NPC162113
0.8455	Intermediate Similarity	NPC319803
0.8448	Intermediate Similarity	NPC53567
0.8447	Intermediate Similarity	NPC80027
0.8435	Intermediate Similarity	NPC39029
0.8435	Intermediate Similarity	NPC476633
0.8431	Intermediate Similarity	NPC473388
0.8431	Intermediate Similarity	NPC216520
0.8431	Intermediate Similarity	NPC292730
0.8431	Intermediate Similarity	NPC82664
0.8431	Intermediate Similarity	NPC132271
0.8407	Intermediate Similarity	NPC206
0.84	Intermediate Similarity	NPC45040
0.8378	Intermediate Similarity	NPC228287
0.8378	Intermediate Similarity	NPC180508
0.8376	Intermediate Similarity	NPC140521
0.8365	Intermediate Similarity	NPC213730
0.8365	Intermediate Similarity	NPC48730
0.8365	Intermediate Similarity	NPC129373
0.8365	Intermediate Similarity	NPC248396
0.8362	Intermediate Similarity	NPC120172
0.8362	Intermediate Similarity	NPC77789
0.8362	Intermediate Similarity	NPC122175
0.8362	Intermediate Similarity	NPC18128
0.8349	Intermediate Similarity	NPC2682
0.8349	Intermediate Similarity	NPC242178
0.8349	Intermediate Similarity	NPC168657
0.8349	Intermediate Similarity	NPC94045
0.8319	Intermediate Similarity	NPC50521
0.8319	Intermediate Similarity	NPC195466
0.8319	Intermediate Similarity	NPC221549
0.8319	Intermediate Similarity	NPC244816
0.8318	Intermediate Similarity	NPC67250
0.8305	Intermediate Similarity	NPC249836
0.8304	Intermediate Similarity	NPC232165
0.8302	Intermediate Similarity	NPC471511
0.8291	Intermediate Similarity	NPC233526
0.8291	Intermediate Similarity	NPC282496
0.8291	Intermediate Similarity	NPC136319
0.8286	Intermediate Similarity	NPC12221
0.8283	Intermediate Similarity	NPC27974
0.8273	Intermediate Similarity	NPC179002
0.8273	Intermediate Similarity	NPC187583
0.8273	Intermediate Similarity	NPC90520
0.8273	Intermediate Similarity	NPC296920
0.8273	Intermediate Similarity	NPC257430
0.8269	Intermediate Similarity	NPC132078
0.8269	Intermediate Similarity	NPC260775
0.8269	Intermediate Similarity	NPC92730
0.8269	Intermediate Similarity	NPC216468
0.8269	Intermediate Similarity	NPC51333
0.8269	Intermediate Similarity	NPC78119
0.8261	Intermediate Similarity	NPC472071
0.8257	Intermediate Similarity	NPC228343
0.8257	Intermediate Similarity	NPC254833
0.8235	Intermediate Similarity	NPC128062
0.823	Intermediate Similarity	NPC229147
0.823	Intermediate Similarity	NPC203113
0.823	Intermediate Similarity	NPC85292
0.823	Intermediate Similarity	NPC54507
0.822	Intermediate Similarity	NPC174729

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 NPC302681 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	999
0.2-0.3	1310
0.3-0.4	2925
0.4-0.5	1941
0.5-0.6	1172
0.6-0.7	460
0.7-0.8	56
0.8-0.85	10
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.91	High Similarity	NPD1242	Phase 1
0.8774	High Similarity	NPD4750	Phase 3
0.8641	High Similarity	NPD846	Approved
0.8641	High Similarity	NPD940	Approved
0.8515	High Similarity	NPD2859	Approved
0.8515	High Similarity	NPD2860	Approved
0.8447	Intermediate Similarity	NPD3020	Approved
0.8416	Intermediate Similarity	NPD2934	Approved
0.8416	Intermediate Similarity	NPD2933	Approved
0.8257	Intermediate Similarity	NPD3022	Approved
0.8257	Intermediate Similarity	NPD3021	Approved
0.8155	Intermediate Similarity	NPD844	Approved
0.7905	Intermediate Similarity	NPD288	Approved
0.7886	Intermediate Similarity	NPD3027	Phase 3
0.7885	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD7635	Approved
0.785	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD9089	Approved
0.7748	Intermediate Similarity	NPD2342	Discontinued
0.7742	Intermediate Similarity	NPD4625	Phase 3
0.7686	Intermediate Similarity	NPD4749	Approved
0.7667	Intermediate Similarity	NPD1610	Phase 2
0.7661	Intermediate Similarity	NPD4908	Phase 1
0.7661	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD9093	Approved
0.7627	Intermediate Similarity	NPD1548	Phase 1
0.7619	Intermediate Similarity	NPD845	Approved
0.7611	Intermediate Similarity	NPD1792	Phase 2
0.7581	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD111	Approved
0.7523	Intermediate Similarity	NPD3028	Approved
0.7521	Intermediate Similarity	NPD6671	Approved
0.75	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1445	Approved
0.75	Intermediate Similarity	NPD1444	Approved
0.7442	Intermediate Similarity	NPD2568	Approved
0.7422	Intermediate Similarity	NPD1613	Approved
0.7422	Intermediate Similarity	NPD943	Approved
0.7422	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD2228	Approved
0.735	Intermediate Similarity	NPD2234	Approved
0.735	Intermediate Similarity	NPD2229	Approved
0.7333	Intermediate Similarity	NPD3091	Approved
0.7315	Intermediate Similarity	NPD1809	Phase 2
0.7308	Intermediate Similarity	NPD9094	Approved
0.7288	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD3094	Phase 2
0.7273	Intermediate Similarity	NPD4093	Discontinued
0.7258	Intermediate Similarity	NPD2982	Phase 2
0.7258	Intermediate Similarity	NPD2983	Phase 2
0.7258	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD1201	Approved
0.7236	Intermediate Similarity	NPD3092	Approved
0.7236	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD2286	Discontinued
0.7213	Intermediate Similarity	NPD4059	Approved
0.7213	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD3019	Approved
0.7213	Intermediate Similarity	NPD2932	Approved
0.7209	Intermediate Similarity	NPD6405	Approved
0.7209	Intermediate Similarity	NPD6407	Approved
0.7203	Intermediate Similarity	NPD5283	Phase 1
0.7193	Intermediate Similarity	NPD968	Approved
0.7182	Intermediate Similarity	NPD9273	Approved
0.7177	Intermediate Similarity	NPD2981	Phase 2
0.7167	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2861	Phase 2
0.7165	Intermediate Similarity	NPD3018	Phase 2
0.7143	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD6100	Approved
0.7132	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD422	Phase 1
0.7094	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD858	Approved
0.7087	Intermediate Similarity	NPD602	Approved
0.7087	Intermediate Similarity	NPD599	Approved
0.7087	Intermediate Similarity	NPD859	Approved
0.708	Intermediate Similarity	NPD9500	Approved
0.7073	Intermediate Similarity	NPD3095	Discontinued
0.7068	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5311	Approved
0.7063	Intermediate Similarity	NPD5310	Approved
0.7049	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD228	Approved
0.7009	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1793	Approved
0.7	Intermediate Similarity	NPD1791	Approved
0.7	Intermediate Similarity	NPD497	Approved
0.6984	Remote Similarity	NPD4659	Approved
0.6975	Remote Similarity	NPD9379	Approved
0.6975	Remote Similarity	NPD9377	Approved
0.6953	Remote Similarity	NPD6584	Phase 3
0.694	Remote Similarity	NPD1510	Phase 2
0.6939	Remote Similarity	NPD9087	Approved
0.6935	Remote Similarity	NPD1751	Approved
0.6935	Remote Similarity	NPD4589	Approved
0.6934	Remote Similarity	NPD3892	Phase 2
0.6934	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD495	Approved
0.6917	Remote Similarity	NPD498	Approved
0.6917	Remote Similarity	NPD5314	Approved
0.6917	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD496	Approved
0.6911	Remote Similarity	NPD5303	Approved
0.6911	Remote Similarity	NPD5304	Approved
0.6911	Remote Similarity	NPD7330	Discontinued
0.6906	Remote Similarity	NPD7390	Discontinued
0.6905	Remote Similarity	NPD9269	Phase 2
0.6905	Remote Similarity	NPD2232	Approved
0.6905	Remote Similarity	NPD2562	Approved
0.6905	Remote Similarity	NPD2233	Approved
0.6905	Remote Similarity	NPD1608	Approved
0.6905	Remote Similarity	NPD2230	Approved
0.6905	Remote Similarity	NPD2561	Approved
0.6899	Remote Similarity	NPD5736	Approved
0.6894	Remote Similarity	NPD3062	Approved
0.6894	Remote Similarity	NPD3059	Approved
0.6894	Remote Similarity	NPD1555	Discontinued
0.6894	Remote Similarity	NPD2238	Phase 2
0.6894	Remote Similarity	NPD3061	Approved
0.6894	Remote Similarity	NPD6346	Approved
0.6894	Remote Similarity	NPD1240	Approved
0.6889	Remote Similarity	NPD5405	Approved
0.6889	Remote Similarity	NPD5406	Approved
0.6889	Remote Similarity	NPD5404	Approved
0.6889	Remote Similarity	NPD5408	Approved
0.688	Remote Similarity	NPD1981	Approved
0.688	Remote Similarity	NPD1980	Approved
0.688	Remote Similarity	NPD1983	Approved
0.6875	Remote Similarity	NPD3053	Approved
0.6875	Remote Similarity	NPD3055	Approved
0.6875	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4103	Phase 2
0.687	Remote Similarity	NPD9608	Approved
0.687	Remote Similarity	NPD9610	Approved
0.6864	Remote Similarity	NPD5451	Approved
0.686	Remote Similarity	NPD9614	Approved
0.686	Remote Similarity	NPD9618	Approved
0.6857	Remote Similarity	NPD7447	Phase 1
0.6855	Remote Similarity	NPD9268	Approved
0.685	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7266	Discontinued
0.6833	Remote Similarity	NPD7843	Approved
0.6833	Remote Similarity	NPD5535	Approved
0.6832	Remote Similarity	NPD9088	Approved
0.6812	Remote Similarity	NPD3750	Approved
0.6803	Remote Similarity	NPD7157	Approved
0.6803	Remote Similarity	NPD709	Approved
0.68	Remote Similarity	NPD9384	Approved
0.68	Remote Similarity	NPD9381	Approved
0.6797	Remote Similarity	NPD6696	Suspended
0.6794	Remote Similarity	NPD7095	Approved
0.6791	Remote Similarity	NPD1607	Approved
0.6783	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2684	Approved
0.6774	Remote Similarity	NPD7741	Discontinued
0.6774	Remote Similarity	NPD1759	Phase 1
0.6772	Remote Similarity	NPD2231	Phase 2
0.6772	Remote Similarity	NPD2235	Phase 2
0.6767	Remote Similarity	NPD4060	Phase 1
0.6765	Remote Similarity	NPD2935	Discontinued
0.6748	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3847	Discontinued
0.6746	Remote Similarity	NPD3023	Approved
0.6746	Remote Similarity	NPD3026	Approved
0.6744	Remote Similarity	NPD1164	Approved
0.6744	Remote Similarity	NPD2797	Approved
0.6742	Remote Similarity	NPD3764	Approved
0.6742	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD9294	Approved
0.672	Remote Similarity	NPD3025	Approved
0.672	Remote Similarity	NPD3024	Approved
0.6719	Remote Similarity	NPD6582	Phase 2
0.6719	Remote Similarity	NPD6583	Phase 3
0.6719	Remote Similarity	NPD1755	Approved
0.6715	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4818	Approved
0.6696	Remote Similarity	NPD4817	Approved
0.6695	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD9613	Approved
0.6694	Remote Similarity	NPD9616	Approved
0.6694	Remote Similarity	NPD856	Approved
0.6694	Remote Similarity	NPD9615	Approved
0.6694	Remote Similarity	NPD16	Approved
0.6694	Remote Similarity	NPD1758	Phase 1
0.6693	Remote Similarity	NPD1091	Approved
0.6692	Remote Similarity	NPD2194	Approved
0.6692	Remote Similarity	NPD7451	Discontinued
0.6692	Remote Similarity	NPD2195	Approved
0.6692	Remote Similarity	NPD6663	Approved
0.6691	Remote Similarity	NPD3299	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