NPASS Compound

Structure

NPC10154 OpenBabel07101718322D 33 35 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.6340 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 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -8.0981 1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5981 1.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5981 0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5981 1.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0981 2.8301 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 -5.5981 0.2321 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 -2.5981 -2.5000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0981 1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0981 2.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5981 3.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 21 2 0 0 0 0 6 21 1 0 0 0 0 7 17 1 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 21 1 0 0 0 0 9 12 1 0 0 0 0 9 22 2 0 0 0 0 10 13 2 0 0 0 0 10 22 1 0 0 0 0 11 15 2 0 0 0 0 11 22 1 0 0 0 0 12 23 2 0 0 0 0 13 23 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 19 1 0 0 0 0 16 24 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 27 1 0 0 0 0 20 33 1 0 0 0 0 23 30 1 0 0 0 0 24 27 1 6 0 0 0 24 28 1 0 0 0 0 25 28 1 6 0 0 0 25 29 1 0 0 0 0 26 31 2 0 0 0 0 26 33 1 0 0 0 0 27 3 1 1 0 0 0 28 4 1 6 0 0 0 29 5 1 6 0 0 0 29 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.29
Volume:	501.176
LogP:	5.629
LogD:	4.557
LogS:	-5.185
# Rotatable Bonds:	9
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.27
Synthetic Accessibility Score:	4.418
Fsp3:	0.552
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.188
MDCK Permeability:	2.3010374206933193e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	98.10535430908203%
Volume Distribution (VD):	0.573
Pgp-substrate:	1.6935728788375854%

ADMET: Metabolism

CYP1A2-inhibitor:	0.145
CYP1A2-substrate:	0.266
CYP2C19-inhibitor:	0.486
CYP2C19-substrate:	0.735
CYP2C9-inhibitor:	0.335
CYP2C9-substrate:	0.722
CYP2D6-inhibitor:	0.553
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.557

ADMET: Excretion

Clearance (CL):	9.19
Half-life (T1/2):	0.569

ADMET: Toxicity

hERG Blockers:	0.312
Human Hepatotoxicity (H-HT):	0.201
Drug-inuced Liver Injury (DILI):	0.389
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.958
Carcinogencity:	0.205
Eye Corrosion:	0.004
Eye Irritation:	0.189
Respiratory Toxicity:	0.826

Download Data

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

Natural Product: NPC10154

Natural Product ID:	NPC10154
*Common Name:**	8Alpha-Hydroxylabda-13(16),14-Dien-19-Yl-(E)-Coumarate
IUPAC Name:	[(1S,4aS,5R,6R,8aR)-6-hydroxy-1,4a,6-trimethyl-5-(3-methylidenepent-4-enyl)-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	LXORINFASUBZBQ-JXZRNQGZSA-N
Standard InCHI:	InChI=1S/C29H40O4/c1-6-21(2)8-14-25-28(4)18-7-17-27(3,24(28)16-19-29(25,5)32)20-33-26(31)15-11-22-9-12-23(30)13-10-22/h6,9-13,15,24-25,30,32H,1-2,7-8,14,16-20H2,3-5H3/b15-11+/t24-,25+,27+,28-,29+/m0/s1
SMILES:	C=CC(=C)CC[C@H]1[C@](C)(O)CC[C@@H]2[C@]1(C)CCC[C@]2(C)COC(=O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689215
PubChem CID:	14138895
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	stem	n.a.	PMID[21226514]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21226514]
NPO32847	fokienia hodginsii	Species	Cupressaceae	Eukaryota	Twigs and Leaves	n.a.	n.a.	PMID[23691952]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6741	Metasequoia glyptostroboides	Species	Cupressaceae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	14300.0	nM	PMID[452861]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	19300.0	nM	PMID[452862]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16580.0	nM	PMID[452862]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	20350.0	nM	PMID[452862]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	15480.0	nM	PMID[452862]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	11770.0	nM	PMID[452862]

☑ 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 NPC10154 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	240
0.1-0.2	1256
0.2-0.3	2254
0.3-0.4	5367
0.4-0.5	10271
0.5-0.6	9806
0.6-0.7	11265
0.7-0.8	2093
0.8-0.85	109
0.85-0.9	31
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC265413
0.9339	High Similarity	NPC474532
0.9274	High Similarity	NPC86257
0.9262	High Similarity	NPC137416
0.9062	High Similarity	NPC11266
0.8992	High Similarity	NPC173569
0.8992	High Similarity	NPC477874
0.8968	High Similarity	NPC288290
0.8931	High Similarity	NPC76032
0.8931	High Similarity	NPC132723
0.8923	High Similarity	NPC249817
0.8862	High Similarity	NPC478058
0.8855	High Similarity	NPC22676
0.8855	High Similarity	NPC475482
0.8855	High Similarity	NPC198621
0.8855	High Similarity	NPC216940
0.8797	High Similarity	NPC172311
0.8788	High Similarity	NPC248287
0.8788	High Similarity	NPC139243
0.8788	High Similarity	NPC182249
0.8788	High Similarity	NPC116742
0.8788	High Similarity	NPC234548
0.8769	High Similarity	NPC194970
0.8722	High Similarity	NPC470617
0.8722	High Similarity	NPC155192
0.8722	High Similarity	NPC473591
0.8722	High Similarity	NPC470616
0.8722	High Similarity	NPC271494
0.8712	High Similarity	NPC471152
0.8672	High Similarity	NPC30174
0.8657	High Similarity	NPC473612
0.8657	High Similarity	NPC304110
0.8657	High Similarity	NPC472801
0.8657	High Similarity	NPC27518
0.8644	High Similarity	NPC139946
0.8603	High Similarity	NPC25491
0.8593	High Similarity	NPC35212
0.8559	High Similarity	NPC183700
0.855	High Similarity	NPC18982
0.855	High Similarity	NPC475457
0.855	High Similarity	NPC475627
0.855	High Similarity	NPC475346
0.8529	High Similarity	NPC252133
0.8529	High Similarity	NPC310621
0.8529	High Similarity	NPC235557
0.8529	High Similarity	NPC477873
0.8529	High Similarity	NPC469447
0.8525	High Similarity	NPC122117
0.8496	Intermediate Similarity	NPC476699
0.8468	Intermediate Similarity	NPC260832
0.8468	Intermediate Similarity	NPC135467
0.8467	Intermediate Similarity	NPC26045
0.8406	Intermediate Similarity	NPC53520
0.8406	Intermediate Similarity	NPC307205
0.8394	Intermediate Similarity	NPC204644
0.8387	Intermediate Similarity	NPC42657
0.8385	Intermediate Similarity	NPC131684
0.8345	Intermediate Similarity	NPC66894
0.8345	Intermediate Similarity	NPC8102
0.8321	Intermediate Similarity	NPC249425
0.8319	Intermediate Similarity	NPC75272
0.8319	Intermediate Similarity	NPC471954
0.8308	Intermediate Similarity	NPC176590
0.8306	Intermediate Similarity	NPC203124
0.8305	Intermediate Similarity	NPC260952
0.8298	Intermediate Similarity	NPC292206
0.8284	Intermediate Similarity	NPC279463
0.8284	Intermediate Similarity	NPC472804
0.8279	Intermediate Similarity	NPC41851
0.8279	Intermediate Similarity	NPC268160
0.8273	Intermediate Similarity	NPC271607
0.8273	Intermediate Similarity	NPC19862
0.8273	Intermediate Similarity	NPC235195
0.8273	Intermediate Similarity	NPC280717
0.8271	Intermediate Similarity	NPC185777
0.8268	Intermediate Similarity	NPC325301
0.8268	Intermediate Similarity	NPC121168
0.8268	Intermediate Similarity	NPC327070
0.8264	Intermediate Similarity	NPC228425
0.8254	Intermediate Similarity	NPC164852
0.8254	Intermediate Similarity	NPC470848
0.8254	Intermediate Similarity	NPC470849
0.824	Intermediate Similarity	NPC263386
0.824	Intermediate Similarity	NPC141791
0.8235	Intermediate Similarity	NPC470039
0.8235	Intermediate Similarity	NPC206341
0.8227	Intermediate Similarity	NPC32017
0.8227	Intermediate Similarity	NPC96930
0.8227	Intermediate Similarity	NPC325032
0.8227	Intermediate Similarity	NPC477483
0.8217	Intermediate Similarity	NPC470765
0.8217	Intermediate Similarity	NPC275576
0.8214	Intermediate Similarity	NPC320734
0.8211	Intermediate Similarity	NPC35797
0.8211	Intermediate Similarity	NPC192948
0.8211	Intermediate Similarity	NPC147179
0.8201	Intermediate Similarity	NPC96447
0.8189	Intermediate Similarity	NPC162935
0.8189	Intermediate Similarity	NPC249340
0.8175	Intermediate Similarity	NPC471875
0.8169	Intermediate Similarity	NPC473719
0.8169	Intermediate Similarity	NPC279442
0.8169	Intermediate Similarity	NPC273358
0.8169	Intermediate Similarity	NPC298647
0.8168	Intermediate Similarity	NPC229894
0.8162	Intermediate Similarity	NPC477592
0.816	Intermediate Similarity	NPC309434
0.8154	Intermediate Similarity	NPC169913
0.8154	Intermediate Similarity	NPC470753
0.8154	Intermediate Similarity	NPC473220
0.8145	Intermediate Similarity	NPC38893
0.8145	Intermediate Similarity	NPC308311
0.8145	Intermediate Similarity	NPC219112
0.8145	Intermediate Similarity	NPC470820
0.8145	Intermediate Similarity	NPC141001
0.8145	Intermediate Similarity	NPC308828
0.8145	Intermediate Similarity	NPC477137
0.8145	Intermediate Similarity	NPC471668
0.8134	Intermediate Similarity	NPC472591
0.812	Intermediate Similarity	NPC18798
0.812	Intermediate Similarity	NPC258073
0.812	Intermediate Similarity	NPC304638
0.812	Intermediate Similarity	NPC191395
0.8116	Intermediate Similarity	NPC138149
0.8115	Intermediate Similarity	NPC26615
0.8112	Intermediate Similarity	NPC470618
0.8112	Intermediate Similarity	NPC145527
0.8112	Intermediate Similarity	NPC327962
0.8112	Intermediate Similarity	NPC470619
0.8112	Intermediate Similarity	NPC208785
0.811	Intermediate Similarity	NPC241001
0.8106	Intermediate Similarity	NPC117899
0.8102	Intermediate Similarity	NPC477593
0.8099	Intermediate Similarity	NPC141782
0.8099	Intermediate Similarity	NPC63345
0.8099	Intermediate Similarity	NPC133308
0.8088	Intermediate Similarity	NPC120852
0.8088	Intermediate Similarity	NPC154485
0.8088	Intermediate Similarity	NPC471872
0.8083	Intermediate Similarity	NPC11554
0.808	Intermediate Similarity	NPC477136
0.808	Intermediate Similarity	NPC304510
0.808	Intermediate Similarity	NPC172219
0.8077	Intermediate Similarity	NPC124030
0.8074	Intermediate Similarity	NPC477594
0.8071	Intermediate Similarity	NPC474599
0.8065	Intermediate Similarity	NPC474967
0.806	Intermediate Similarity	NPC165612
0.8058	Intermediate Similarity	NPC477595
0.8058	Intermediate Similarity	NPC20631
0.8058	Intermediate Similarity	NPC93640
0.8056	Intermediate Similarity	NPC118033
0.8049	Intermediate Similarity	NPC190212
0.8047	Intermediate Similarity	NPC147654
0.8047	Intermediate Similarity	NPC253627
0.8047	Intermediate Similarity	NPC251259
0.8045	Intermediate Similarity	NPC472793
0.8043	Intermediate Similarity	NPC79372
0.8033	Intermediate Similarity	NPC322753
0.8033	Intermediate Similarity	NPC260323
0.8033	Intermediate Similarity	NPC77772
0.8033	Intermediate Similarity	NPC176279
0.8031	Intermediate Similarity	NPC478121
0.8031	Intermediate Similarity	NPC328485
0.803	Intermediate Similarity	NPC193203
0.8029	Intermediate Similarity	NPC306365
0.8029	Intermediate Similarity	NPC131198
0.8028	Intermediate Similarity	NPC472936
0.8028	Intermediate Similarity	NPC472938
0.8028	Intermediate Similarity	NPC472937
0.8017	Intermediate Similarity	NPC79543
0.8016	Intermediate Similarity	NPC254233
0.8016	Intermediate Similarity	NPC164649
0.8016	Intermediate Similarity	NPC48342
0.8016	Intermediate Similarity	NPC469609
0.8016	Intermediate Similarity	NPC275519
0.8016	Intermediate Similarity	NPC471671
0.8015	Intermediate Similarity	NPC43353
0.8015	Intermediate Similarity	NPC477596
0.8015	Intermediate Similarity	NPC5486
0.8015	Intermediate Similarity	NPC71610
0.8014	Intermediate Similarity	NPC169942
0.8	Intermediate Similarity	NPC469663
0.8	Intermediate Similarity	NPC137496
0.8	Intermediate Similarity	NPC281277
0.8	Intermediate Similarity	NPC105141
0.8	Intermediate Similarity	NPC154511
0.8	Intermediate Similarity	NPC257540
0.8	Intermediate Similarity	NPC242764
0.8	Intermediate Similarity	NPC92
0.8	Intermediate Similarity	NPC211352
0.8	Intermediate Similarity	NPC471936
0.8	Intermediate Similarity	NPC474387
0.8	Intermediate Similarity	NPC475579
0.8	Intermediate Similarity	NPC474358
0.8	Intermediate Similarity	NPC247858
0.8	Intermediate Similarity	NPC473773
0.8	Intermediate Similarity	NPC49742
0.7986	Intermediate Similarity	NPC116292
0.7986	Intermediate Similarity	NPC267469

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 NPC10154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	837
0.2-0.3	1247
0.3-0.4	2404
0.4-0.5	2312
0.5-0.6	1446
0.6-0.7	611
0.7-0.8	76
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8516	High Similarity	NPD5736	Approved
0.8456	Intermediate Similarity	NPD8166	Discontinued
0.8258	Intermediate Similarity	NPD6663	Approved
0.806	Intermediate Similarity	NPD4140	Approved
0.8031	Intermediate Similarity	NPD4626	Approved
0.8016	Intermediate Similarity	NPD3091	Approved
0.7953	Intermediate Similarity	NPD5691	Approved
0.7926	Intermediate Similarity	NPD4060	Phase 1
0.7891	Intermediate Similarity	NPD3019	Approved
0.7836	Intermediate Similarity	NPD7095	Approved
0.7801	Intermediate Similarity	NPD7003	Approved
0.7778	Intermediate Similarity	NPD3764	Approved
0.7778	Intermediate Similarity	NPD4198	Discontinued
0.7769	Intermediate Similarity	NPD3092	Approved
0.7752	Intermediate Similarity	NPD3095	Discontinued
0.7752	Intermediate Similarity	NPD4059	Approved
0.7752	Intermediate Similarity	NPD2932	Approved
0.7712	Intermediate Similarity	NPD3020	Approved
0.7676	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3094	Phase 2
0.7655	Intermediate Similarity	NPD6273	Approved
0.7652	Intermediate Similarity	NPD5327	Phase 3
0.7623	Intermediate Similarity	NPD3134	Approved
0.7619	Intermediate Similarity	NPD7458	Discontinued
0.7612	Intermediate Similarity	NPD4624	Approved
0.7591	Intermediate Similarity	NPD8032	Phase 2
0.7557	Intermediate Similarity	NPD3496	Discontinued
0.7554	Intermediate Similarity	NPD6353	Approved
0.754	Intermediate Similarity	NPD5535	Approved
0.7521	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7097	Phase 1
0.7482	Intermediate Similarity	NPD5735	Approved
0.7465	Intermediate Similarity	NPD7266	Discontinued
0.7463	Intermediate Similarity	NPD1283	Approved
0.7458	Intermediate Similarity	NPD2860	Approved
0.7458	Intermediate Similarity	NPD2859	Approved
0.7445	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3021	Approved
0.744	Intermediate Similarity	NPD3022	Approved
0.7431	Intermediate Similarity	NPD4628	Phase 3
0.7424	Intermediate Similarity	NPD3023	Approved
0.7424	Intermediate Similarity	NPD3026	Approved
0.7419	Intermediate Similarity	NPD1358	Approved
0.741	Intermediate Similarity	NPD3620	Phase 2
0.741	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2797	Approved
0.7405	Intermediate Similarity	NPD3024	Approved
0.7405	Intermediate Similarity	NPD3025	Approved
0.7402	Intermediate Similarity	NPD7635	Approved
0.7394	Intermediate Similarity	NPD2935	Discontinued
0.7391	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD2933	Approved
0.7373	Intermediate Similarity	NPD2934	Approved
0.7372	Intermediate Similarity	NPD4908	Phase 1
0.7364	Intermediate Similarity	NPD7157	Approved
0.7361	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6355	Discontinued
0.7355	Intermediate Similarity	NPD8127	Discontinued
0.7343	Intermediate Similarity	NPD5762	Approved
0.7343	Intermediate Similarity	NPD5763	Approved
0.7329	Intermediate Similarity	NPD7236	Approved
0.7328	Intermediate Similarity	NPD7741	Discontinued
0.7328	Intermediate Similarity	NPD9545	Approved
0.7324	Intermediate Similarity	NPD2799	Discontinued
0.7323	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD1809	Phase 2
0.7305	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4097	Suspended
0.7287	Intermediate Similarity	NPD5951	Approved
0.7286	Intermediate Similarity	NPD2979	Phase 3
0.728	Intermediate Similarity	NPD2342	Discontinued
0.7273	Intermediate Similarity	NPD5404	Approved
0.7273	Intermediate Similarity	NPD5406	Approved
0.7273	Intermediate Similarity	NPD5405	Approved
0.7273	Intermediate Similarity	NPD5408	Approved
0.7273	Intermediate Similarity	NPD5585	Approved
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6798	Discontinued
0.7266	Intermediate Similarity	NPD3268	Approved
0.725	Intermediate Similarity	NPD288	Approved
0.7239	Intermediate Similarity	NPD1281	Approved
0.7234	Intermediate Similarity	NPD5124	Phase 1
0.7234	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6671	Approved
0.7226	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD1778	Approved
0.7213	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7008	Discontinued
0.7192	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4110	Phase 3
0.7174	Intermediate Similarity	NPD2861	Phase 2
0.7167	Intermediate Similarity	NPD844	Approved
0.7164	Intermediate Similarity	NPD3847	Discontinued
0.7154	Intermediate Similarity	NPD2629	Approved
0.7153	Intermediate Similarity	NPD6100	Approved
0.7153	Intermediate Similarity	NPD1470	Approved
0.7153	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD4093	Discontinued
0.7143	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD845	Approved
0.7132	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1610	Phase 2
0.7111	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD422	Phase 1
0.7111	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1611	Approved
0.7111	Intermediate Similarity	NPD1201	Approved
0.7103	Intermediate Similarity	NPD2346	Discontinued
0.7101	Intermediate Similarity	NPD6584	Phase 3
0.7097	Intermediate Similarity	NPD7768	Phase 2
0.709	Intermediate Similarity	NPD1751	Approved
0.7087	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7239	Suspended
0.7083	Intermediate Similarity	NPD4308	Phase 3
0.7083	Intermediate Similarity	NPD7742	Approved
0.7083	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7743	Approved
0.708	Intermediate Similarity	NPD8651	Approved
0.708	Intermediate Similarity	NPD6696	Suspended
0.7078	Intermediate Similarity	NPD7819	Suspended
0.7077	Intermediate Similarity	NPD2229	Approved
0.7077	Intermediate Similarity	NPD2228	Approved
0.7077	Intermediate Similarity	NPD2234	Approved
0.7077	Intermediate Similarity	NPD5283	Phase 1
0.7075	Intermediate Similarity	NPD3750	Approved
0.7071	Intermediate Similarity	NPD4625	Phase 3
0.7067	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2230	Approved
0.7059	Intermediate Similarity	NPD2233	Approved
0.7059	Intermediate Similarity	NPD2232	Approved
0.7059	Intermediate Similarity	NPD3972	Approved
0.7045	Intermediate Similarity	NPD9493	Approved
0.7042	Intermediate Similarity	NPD6346	Approved
0.704	Intermediate Similarity	NPD5909	Discontinued
0.7034	Intermediate Similarity	NPD2531	Phase 2
0.7034	Intermediate Similarity	NPD2438	Suspended
0.7034	Intermediate Similarity	NPD4477	Approved
0.7034	Intermediate Similarity	NPD4476	Approved
0.7031	Intermediate Similarity	NPD4750	Phase 3
0.7029	Intermediate Similarity	NPD1164	Approved
0.7027	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1651	Approved
0.7015	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4359	Approved
0.7007	Intermediate Similarity	NPD6582	Phase 2
0.7007	Intermediate Similarity	NPD4749	Approved
0.7007	Intermediate Similarity	NPD6583	Phase 3
0.7	Intermediate Similarity	NPD2606	Approved
0.7	Intermediate Similarity	NPD2605	Approved
0.7	Intermediate Similarity	NPD7843	Approved
0.6993	Remote Similarity	NPD7028	Phase 2
0.698	Remote Similarity	NPD6667	Approved
0.698	Remote Similarity	NPD6666	Approved
0.6978	Remote Similarity	NPD2798	Approved
0.6972	Remote Similarity	NPD6233	Phase 2
0.6963	Remote Similarity	NPD2286	Discontinued
0.6963	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2668	Approved
0.6963	Remote Similarity	NPD2667	Approved
0.696	Remote Similarity	NPD6647	Phase 2
0.6953	Remote Similarity	NPD2684	Approved
0.695	Remote Similarity	NPD5156	Approved
0.695	Remote Similarity	NPD5155	Approved
0.694	Remote Similarity	NPD1894	Discontinued
0.6939	Remote Similarity	NPD7037	Approved
0.6939	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1608	Approved
0.6933	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7041	Phase 2
0.6929	Remote Similarity	NPD3636	Approved
0.6929	Remote Similarity	NPD3635	Approved
0.6929	Remote Similarity	NPD3637	Approved
0.6929	Remote Similarity	NPD4208	Discontinued
0.6928	Remote Similarity	NPD3226	Approved
0.6917	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7340	Approved
0.6908	Remote Similarity	NPD5699	Approved
0.6906	Remote Similarity	NPD3267	Approved
0.6906	Remote Similarity	NPD3266	Approved
0.6906	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD37	Approved
0.6901	Remote Similarity	NPD2313	Discontinued
0.6899	Remote Similarity	NPD5451	Approved
0.6899	Remote Similarity	NPD6234	Discontinued
0.6899	Remote Similarity	NPD1792	Phase 2
0.6897	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.688	Remote Similarity	NPD846	Approved
0.688	Remote Similarity	NPD940	Approved
0.6879	Remote Similarity	NPD3595	Approved
0.6879	Remote Similarity	NPD6832	Phase 2
0.6879	Remote Similarity	NPD4966	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