NPASS Compound

Structure

NPC475002 OpenBabel07101718182D 24 26 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 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 0.8660 1.5000 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 -2.5981 -0.5000 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 0.8660 -1.5000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -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 -2.5981 -1.5000 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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 4.2321 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 6 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 3 1 6 0 0 0 21 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.22
Volume:	361.928
LogP:	4.204
LogD:	2.557
LogS:	-3.652
# Rotatable Bonds:	3
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.863
Synthetic Accessibility Score:	3.756
Fsp3:	0.667
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:	-5.003
MDCK Permeability:	3.163187648169696e-05
Pgp-inhibitor:	0.224
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.204
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.182
Plasma Protein Binding (PPB):	90.9828109741211%
Volume Distribution (VD):	0.367
Pgp-substrate:	10.209395408630371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.364
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.788
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.291
CYP3A4-inhibitor:	0.118
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	2.919
Half-life (T1/2):	0.366

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.319
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.166
Maximum Recommended Daily Dose:	0.828
Skin Sensitization:	0.244
Carcinogencity:	0.59
Eye Corrosion:	0.004
Eye Irritation:	0.02
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC475002

Natural Product ID:	NPC475002
*Common Name:**	Abieta-8,11,13-Triene-15,18-Diol
IUPAC Name:	2-[(1S,4aS,10aS)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]acetic acid
Synonyms:
Standard InCHIKey:	QMTZBWPBIQZLBJ-DZFGPLHGSA-N
Standard InCHI:	InChI=1S/C21H30O3/c1-19(2,24)15-7-8-16-14(12-15)6-9-17-20(3,13-18(22)23)10-5-11-21(16,17)4/h7-8,12,17,24H,5-6,9-11,13H2,1-4H3,(H,22,23)/t17-,20-,21+/m0/s1
SMILES:	OC(=O)C[C@]1(C)CCC[C@]2([C@H]1CCc1c2ccc(c1)C(O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491539
PubChem CID:	44566201
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
NPO24264	Pinus luchuensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502340]
NPO24264	Pinus luchuensis	Species	Pinaceae	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
Others	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[536688]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[536688]
NPT2	Others	Unspecified		Activity	=	33.4	%	PMID[536688]
NPT2	Others	Unspecified		Activity	=	72.5	%	PMID[536688]
NPT2	Others	Unspecified		Activity	=	96.4	%	PMID[536688]

☑ 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 NPC475002 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	215
0.1-0.2	1119
0.2-0.3	1986
0.3-0.4	6363
0.4-0.5	13436
0.5-0.6	14914
0.6-0.7	4041
0.7-0.8	536
0.8-0.85	47
0.85-0.9	27
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC95126
0.9444	High Similarity	NPC212891
0.9439	High Similarity	NPC221275
0.9182	High Similarity	NPC45794
0.9159	High Similarity	NPC471188
0.9118	High Similarity	NPC128248
0.9118	High Similarity	NPC133809
0.9118	High Similarity	NPC225079
0.9118	High Similarity	NPC136810
0.9048	High Similarity	NPC94751
0.9048	High Similarity	NPC142326
0.8947	High Similarity	NPC269923
0.8947	High Similarity	NPC369
0.8947	High Similarity	NPC167323
0.8947	High Similarity	NPC293831
0.8938	High Similarity	NPC133389
0.8938	High Similarity	NPC234337
0.8938	High Similarity	NPC183339
0.8919	High Similarity	NPC242764
0.8919	High Similarity	NPC105141
0.8793	High Similarity	NPC85511
0.8774	High Similarity	NPC471186
0.8762	High Similarity	NPC19856
0.8739	High Similarity	NPC186933
0.8684	High Similarity	NPC42657
0.8654	High Similarity	NPC221825
0.8636	High Similarity	NPC66208
0.8621	High Similarity	NPC249340
0.8621	High Similarity	NPC162935
0.8596	High Similarity	NPC254233
0.8571	High Similarity	NPC253681
0.8534	High Similarity	NPC241001
0.8505	High Similarity	NPC472221
0.8505	High Similarity	NPC472222
0.85	High Similarity	NPC51448
0.85	High Similarity	NPC115797
0.8482	Intermediate Similarity	NPC471721
0.8462	Intermediate Similarity	NPC226041
0.844	Intermediate Similarity	NPC472979
0.844	Intermediate Similarity	NPC27252
0.8407	Intermediate Similarity	NPC93181
0.8396	Intermediate Similarity	NPC469481
0.8393	Intermediate Similarity	NPC93287
0.839	Intermediate Similarity	NPC121168
0.8378	Intermediate Similarity	NPC474057
0.8378	Intermediate Similarity	NPC133308
0.8364	Intermediate Similarity	NPC318327
0.8319	Intermediate Similarity	NPC77691
0.8304	Intermediate Similarity	NPC471189
0.8273	Intermediate Similarity	NPC472980
0.8261	Intermediate Similarity	NPC158157
0.8257	Intermediate Similarity	NPC243601
0.8235	Intermediate Similarity	NPC182333
0.8235	Intermediate Similarity	NPC273336
0.822	Intermediate Similarity	NPC164852
0.822	Intermediate Similarity	NPC259703
0.822	Intermediate Similarity	NPC32322
0.822	Intermediate Similarity	NPC472981
0.8198	Intermediate Similarity	NPC149455
0.8198	Intermediate Similarity	NPC64642
0.8198	Intermediate Similarity	NPC475006
0.8198	Intermediate Similarity	NPC472982
0.8148	Intermediate Similarity	NPC304873
0.8136	Intermediate Similarity	NPC318552
0.8136	Intermediate Similarity	NPC190501
0.8136	Intermediate Similarity	NPC478121
0.812	Intermediate Similarity	NPC328694
0.8115	Intermediate Similarity	NPC5486
0.8108	Intermediate Similarity	NPC249811
0.8108	Intermediate Similarity	NPC21929
0.8095	Intermediate Similarity	NPC172925
0.8091	Intermediate Similarity	NPC105899
0.8083	Intermediate Similarity	NPC176208
0.8083	Intermediate Similarity	NPC11250
0.8073	Intermediate Similarity	NPC255676
0.8065	Intermediate Similarity	NPC131684
0.8058	Intermediate Similarity	NPC274455
0.8058	Intermediate Similarity	NPC70940
0.8058	Intermediate Similarity	NPC86670
0.8056	Intermediate Similarity	NPC264728
0.8053	Intermediate Similarity	NPC265513
0.8033	Intermediate Similarity	NPC470765
0.8017	Intermediate Similarity	NPC471187
0.8017	Intermediate Similarity	NPC307139
0.8	Intermediate Similarity	NPC196673
0.8	Intermediate Similarity	NPC253627
0.8	Intermediate Similarity	NPC154696
0.7982	Intermediate Similarity	NPC25458
0.7982	Intermediate Similarity	NPC280789
0.7967	Intermediate Similarity	NPC473220
0.7967	Intermediate Similarity	NPC470753
0.7963	Intermediate Similarity	NPC217621
0.7961	Intermediate Similarity	NPC298115
0.7951	Intermediate Similarity	NPC181334
0.7931	Intermediate Similarity	NPC476357
0.7913	Intermediate Similarity	NPC143768
0.7909	Intermediate Similarity	NPC329556
0.7909	Intermediate Similarity	NPC247976
0.7899	Intermediate Similarity	NPC202015
0.7886	Intermediate Similarity	NPC9180
0.7886	Intermediate Similarity	NPC137750
0.7886	Intermediate Similarity	NPC137416
0.7886	Intermediate Similarity	NPC275576
0.7886	Intermediate Similarity	NPC100402
0.787	Intermediate Similarity	NPC120393
0.787	Intermediate Similarity	NPC229242
0.7869	Intermediate Similarity	NPC198014
0.7869	Intermediate Similarity	NPC473938
0.7869	Intermediate Similarity	NPC275145
0.7864	Intermediate Similarity	NPC329064
0.7863	Intermediate Similarity	NPC9274
0.7863	Intermediate Similarity	NPC469719
0.7857	Intermediate Similarity	NPC244933
0.7857	Intermediate Similarity	NPC85560
0.7857	Intermediate Similarity	NPC37914
0.785	Intermediate Similarity	NPC469893
0.7843	Intermediate Similarity	NPC474211
0.784	Intermediate Similarity	NPC229894
0.7823	Intermediate Similarity	NPC169913
0.7823	Intermediate Similarity	NPC474106
0.7812	Intermediate Similarity	NPC49742
0.781	Intermediate Similarity	NPC220596
0.781	Intermediate Similarity	NPC86987
0.7795	Intermediate Similarity	NPC18798
0.7778	Intermediate Similarity	NPC469891
0.7778	Intermediate Similarity	NPC215419
0.7778	Intermediate Similarity	NPC117899
0.7778	Intermediate Similarity	NPC253423
0.7778	Intermediate Similarity	NPC469890
0.7778	Intermediate Similarity	NPC469892
0.7778	Intermediate Similarity	NPC276238
0.7778	Intermediate Similarity	NPC274839
0.7767	Intermediate Similarity	NPC322387
0.776	Intermediate Similarity	NPC84672
0.776	Intermediate Similarity	NPC78364
0.776	Intermediate Similarity	NPC69424
0.776	Intermediate Similarity	NPC176130
0.7759	Intermediate Similarity	NPC470253
0.7752	Intermediate Similarity	NPC293454
0.775	Intermediate Similarity	NPC473974
0.775	Intermediate Similarity	NPC31296
0.775	Intermediate Similarity	NPC258366
0.775	Intermediate Similarity	NPC79933
0.775	Intermediate Similarity	NPC476645
0.7745	Intermediate Similarity	NPC474354
0.7742	Intermediate Similarity	NPC87985
0.7742	Intermediate Similarity	NPC478107
0.7742	Intermediate Similarity	NPC470649
0.7724	Intermediate Similarity	NPC328107
0.7717	Intermediate Similarity	NPC108129
0.7714	Intermediate Similarity	NPC26224
0.7699	Intermediate Similarity	NPC100767
0.7698	Intermediate Similarity	NPC193203
0.7692	Intermediate Similarity	NPC294458
0.7686	Intermediate Similarity	NPC470585
0.7679	Intermediate Similarity	NPC329282
0.7672	Intermediate Similarity	NPC292834
0.7672	Intermediate Similarity	NPC176279
0.7672	Intermediate Similarity	NPC260323
0.7661	Intermediate Similarity	NPC295664
0.7661	Intermediate Similarity	NPC15127
0.7656	Intermediate Similarity	NPC258073
0.7656	Intermediate Similarity	NPC243305
0.7656	Intermediate Similarity	NPC476847
0.7656	Intermediate Similarity	NPC313663
0.7652	Intermediate Similarity	NPC273837
0.7647	Intermediate Similarity	NPC472862
0.7647	Intermediate Similarity	NPC168855
0.7647	Intermediate Similarity	NPC92
0.7647	Intermediate Similarity	NPC469663
0.7647	Intermediate Similarity	NPC267704
0.7647	Intermediate Similarity	NPC471668
0.7642	Intermediate Similarity	NPC478058
0.7642	Intermediate Similarity	NPC125226
0.7638	Intermediate Similarity	NPC206028
0.7638	Intermediate Similarity	NPC303910
0.7634	Intermediate Similarity	NPC472308
0.7627	Intermediate Similarity	NPC195922
0.7627	Intermediate Similarity	NPC474095
0.7623	Intermediate Similarity	NPC21216
0.7619	Intermediate Similarity	NPC72667
0.7619	Intermediate Similarity	NPC30491
0.7619	Intermediate Similarity	NPC1793
0.7619	Intermediate Similarity	NPC262936
0.7615	Intermediate Similarity	NPC27394
0.7615	Intermediate Similarity	NPC477594
0.7615	Intermediate Similarity	NPC324602
0.7615	Intermediate Similarity	NPC213122
0.7611	Intermediate Similarity	NPC471133
0.7607	Intermediate Similarity	NPC306977
0.7607	Intermediate Similarity	NPC287055
0.7607	Intermediate Similarity	NPC250323
0.7607	Intermediate Similarity	NPC242957
0.7607	Intermediate Similarity	NPC206414
0.7586	Intermediate Similarity	NPC141782
0.7583	Intermediate Similarity	NPC323440
0.7583	Intermediate Similarity	NPC222968
0.7583	Intermediate Similarity	NPC228318
0.7583	Intermediate Similarity	NPC80605
0.7581	Intermediate Similarity	NPC12881

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 NPC475002 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	840
0.2-0.3	1068
0.3-0.4	2582
0.4-0.5	2548
0.5-0.6	1402
0.6-0.7	426
0.7-0.8	74
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9083	High Similarity	NPD5951	Approved
0.8609	High Similarity	NPD7163	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD1088	Approved
0.8198	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD3019	Approved
0.8131	Intermediate Similarity	NPD2066	Phase 3
0.8095	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.8087	Intermediate Similarity	NPD2629	Approved
0.8065	Intermediate Similarity	NPD7008	Discontinued
0.8065	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD1089	Approved
0.8058	Intermediate Similarity	NPD1086	Approved
0.8058	Intermediate Similarity	NPD1090	Approved
0.7983	Intermediate Similarity	NPD2932	Approved
0.7961	Intermediate Similarity	NPD800	Approved
0.7925	Intermediate Similarity	NPD1693	Approved
0.7909	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD1929	Approved
0.7909	Intermediate Similarity	NPD1930	Approved
0.7863	Intermediate Similarity	NPD4198	Discontinued
0.781	Intermediate Similarity	NPD1239	Approved
0.7795	Intermediate Similarity	NPD6663	Approved
0.7778	Intermediate Similarity	NPD1566	Phase 3
0.7778	Intermediate Similarity	NPD1565	Approved
0.7778	Intermediate Similarity	NPD1564	Approved
0.7767	Intermediate Similarity	NPD1087	Approved
0.776	Intermediate Similarity	NPD5736	Approved
0.7757	Intermediate Similarity	NPD6049	Phase 2
0.7757	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5909	Discontinued
0.7664	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD7715	Approved
0.7656	Intermediate Similarity	NPD7714	Approved
0.7623	Intermediate Similarity	NPD3026	Approved
0.7623	Intermediate Similarity	NPD3023	Approved
0.7603	Intermediate Similarity	NPD3025	Approved
0.7603	Intermediate Similarity	NPD3024	Approved
0.7541	Intermediate Similarity	NPD4199	Phase 3
0.7541	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD1989	Approved
0.752	Intermediate Similarity	NPD1283	Approved
0.75	Intermediate Similarity	NPD1563	Approved
0.7481	Intermediate Similarity	NPD7003	Approved
0.7458	Intermediate Similarity	NPD7094	Approved
0.7458	Intermediate Similarity	NPD6858	Approved
0.7455	Intermediate Similarity	NPD3495	Discontinued
0.7453	Intermediate Similarity	NPD5347	Phase 2
0.7453	Intermediate Similarity	NPD5346	Phase 2
0.7438	Intermediate Similarity	NPD7610	Discontinued
0.7436	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD5306	Approved
0.7398	Intermediate Similarity	NPD5305	Approved
0.7387	Intermediate Similarity	NPD9495	Approved
0.7379	Intermediate Similarity	NPD9491	Approved
0.7353	Intermediate Similarity	NPD226	Approved
0.7345	Intermediate Similarity	NPD1932	Approved
0.7328	Intermediate Similarity	NPD2342	Discontinued
0.7317	Intermediate Similarity	NPD4105	Approved
0.7317	Intermediate Similarity	NPD4102	Approved
0.7311	Intermediate Similarity	NPD7635	Approved
0.728	Intermediate Similarity	NPD4807	Approved
0.728	Intermediate Similarity	NPD4806	Approved
0.728	Intermediate Similarity	NPD1281	Approved
0.7273	Intermediate Similarity	NPD3317	Approved
0.7265	Intermediate Similarity	NPD2329	Discontinued
0.7264	Intermediate Similarity	NPD4793	Discontinued
0.7258	Intermediate Similarity	NPD4059	Approved
0.7252	Intermediate Similarity	NPD8032	Phase 2
0.725	Intermediate Similarity	NPD6010	Discontinued
0.725	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD3091	Approved
0.7236	Intermediate Similarity	NPD7009	Phase 2
0.7236	Intermediate Similarity	NPD7741	Discontinued
0.7231	Intermediate Similarity	NPD6966	Discovery
0.7222	Intermediate Similarity	NPD4878	Approved
0.7222	Intermediate Similarity	NPD9256	Approved
0.7222	Intermediate Similarity	NPD9258	Approved
0.7212	Intermediate Similarity	NPD3971	Phase 1
0.72	Intermediate Similarity	NPD4106	Approved
0.72	Intermediate Similarity	NPD4136	Approved
0.72	Intermediate Similarity	NPD4135	Approved
0.7185	Intermediate Similarity	NPD5408	Approved
0.7185	Intermediate Similarity	NPD5404	Approved
0.7185	Intermediate Similarity	NPD5406	Approved
0.7185	Intermediate Similarity	NPD5405	Approved
0.7168	Intermediate Similarity	NPD3020	Approved
0.7165	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7305	Phase 1
0.7101	Intermediate Similarity	NPD8166	Discontinued
0.7069	Intermediate Similarity	NPD1237	Approved
0.7064	Intermediate Similarity	NPD3672	Approved
0.7064	Intermediate Similarity	NPD3673	Approved
0.7059	Intermediate Similarity	NPD227	Approved
0.7059	Intermediate Similarity	NPD225	Approved
0.7054	Intermediate Similarity	NPD2797	Approved
0.7045	Intermediate Similarity	NPD3764	Approved
0.704	Intermediate Similarity	NPD1651	Approved
0.7027	Intermediate Similarity	NPD845	Approved
0.7027	Intermediate Similarity	NPD1202	Approved
0.7009	Intermediate Similarity	NPD5048	Discontinued
0.7008	Intermediate Similarity	NPD3092	Approved
0.7008	Intermediate Similarity	NPD6287	Discontinued
0.7008	Intermediate Similarity	NPD5618	Discontinued
0.7	Intermediate Similarity	NPD7236	Approved
0.7	Intermediate Similarity	NPD6085	Phase 2
0.7	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3642	Approved
0.7	Intermediate Similarity	NPD3644	Approved
0.7	Intermediate Similarity	NPD3643	Approved
0.6992	Remote Similarity	NPD7961	Discontinued
0.699	Remote Similarity	NPD9490	Approved
0.6984	Remote Similarity	NPD7725	Approved
0.6984	Remote Similarity	NPD4626	Approved
0.6984	Remote Similarity	NPD3095	Discontinued
0.6983	Remote Similarity	NPD6647	Phase 2
0.6983	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2182	Approved
0.6964	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1616	Discontinued
0.6942	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2979	Phase 3
0.694	Remote Similarity	NPD4140	Approved
0.6935	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1470	Approved
0.6923	Remote Similarity	NPD164	Approved
0.6917	Remote Similarity	NPD5235	Approved
0.6917	Remote Similarity	NPD5239	Approved
0.6917	Remote Similarity	NPD5237	Approved
0.6917	Remote Similarity	NPD5236	Approved
0.6917	Remote Similarity	NPD5240	Approved
0.6911	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1809	Phase 2
0.6903	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2859	Approved
0.6903	Remote Similarity	NPD2860	Approved
0.6897	Remote Similarity	NPD4818	Approved
0.6897	Remote Similarity	NPD4817	Approved
0.6894	Remote Similarity	NPD4617	Approved
0.6894	Remote Similarity	NPD5203	Approved
0.6894	Remote Similarity	NPD5201	Approved
0.6894	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4620	Approved
0.6884	Remote Similarity	NPD2346	Discontinued
0.6875	Remote Similarity	NPD7239	Suspended
0.687	Remote Similarity	NPD7798	Approved
0.6861	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6273	Approved
0.6852	Remote Similarity	NPD9257	Approved
0.6852	Remote Similarity	NPD9259	Approved
0.685	Remote Similarity	NPD5125	Phase 3
0.685	Remote Similarity	NPD5126	Approved
0.685	Remote Similarity	NPD2345	Approved
0.6842	Remote Similarity	NPD7095	Approved
0.6842	Remote Similarity	NPD288	Approved
0.6838	Remote Similarity	NPD4229	Approved
0.6838	Remote Similarity	NPD4231	Approved
0.6829	Remote Similarity	NPD2650	Approved
0.6829	Remote Similarity	NPD2652	Approved
0.6828	Remote Similarity	NPD7458	Discontinued
0.6822	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1608	Approved
0.6818	Remote Similarity	NPD5204	Approved
0.6815	Remote Similarity	NPD5120	Approved
0.6815	Remote Similarity	NPD5121	Approved
0.6815	Remote Similarity	NPD5119	Approved
0.6814	Remote Similarity	NPD2933	Approved
0.6814	Remote Similarity	NPD2934	Approved
0.6812	Remote Similarity	NPD6099	Approved
0.6812	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6100	Approved
0.6809	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD9508	Approved
0.6797	Remote Similarity	NPD4879	Approved
0.6794	Remote Similarity	NPD3094	Phase 2
0.6794	Remote Similarity	NPD1164	Approved
0.6791	Remote Similarity	NPD3268	Approved
0.6786	Remote Similarity	NPD7631	Approved
0.6777	Remote Similarity	NPD1317	Discontinued
0.6777	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4766	Approved
0.6772	Remote Similarity	NPD6993	Approved
0.6772	Remote Similarity	NPD6994	Approved
0.6763	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD844	Approved
0.6748	Remote Similarity	NPD5277	Phase 2
0.6746	Remote Similarity	NPD6065	Approved
0.6742	Remote Similarity	NPD4980	Approved
0.6742	Remote Similarity	NPD4624	Approved
0.6724	Remote Similarity	NPD1238	Approved
0.6721	Remote Similarity	NPD2201	Approved
0.672	Remote Similarity	NPD255	Approved
0.672	Remote Similarity	NPD256	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