NPASS Compound

Structure

NPC45794 OpenBabel07101719512D 25 27 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 5.6962 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1962 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 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 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 3.4641 2.0000 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 4.3301 1.5000 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 0.8660 0.5000 0.0000 C 0 0 2 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 5.1962 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 1 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 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 6 25 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 17 2 0 0 0 0 11 18 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 21 1 6 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 4 1 6 0 0 0 22 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.24
Volume:	379.224
LogP:	4.935
LogD:	3.814
LogS:	-4.768
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.831
Synthetic Accessibility Score:	3.783
Fsp3:	0.682
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:	-5.014
MDCK Permeability:	2.3970327674760483e-05
Pgp-inhibitor:	0.089
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	95.48177337646484%
Volume Distribution (VD):	0.913
Pgp-substrate:	3.743293523788452%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.834
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.372
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.257
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.289

ADMET: Excretion

Clearance (CL):	1.502
Half-life (T1/2):	0.12

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.138
Skin Sensitization:	0.448
Carcinogencity:	0.046
Eye Corrosion:	0.005
Eye Irritation:	0.114
Respiratory Toxicity:	0.045

Download Data

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

Natural Product: NPC45794

Natural Product ID:	NPC45794
*Common Name:**	Abiesadine P
IUPAC Name:	(1R,4aS,10aR)-7-(2-ethoxypropan-2-yl)-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	LYYQEUOQFQMYRP-STZQEDGTSA-N
Standard InCHI:	InChI=1S/C22H32O3/c1-6-25-20(2,3)16-9-10-17-15(14-16)8-11-18-21(17,4)12-7-13-22(18,5)19(23)24/h9-10,14,18H,6-8,11-13H2,1-5H3,(H,23,24)/t18-,21-,22-/m1/s1
SMILES:	CCOC(c1ccc2c(c1)CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(=O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL590963
PubChem CID:	46230167
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
NPO2882	Abies georgei	Species	Pinaceae	Eukaryota	aerial parts	Zhongdian city, Yunnan Province of China	n.a.	PMID[20022253]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	94.1	ug.mL-1	PMID[511831]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[511831]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[511831]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[511831]

☑ 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 NPC45794 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	208
0.1-0.2	1012
0.2-0.3	1802
0.3-0.4	4942
0.4-0.5	10770
0.5-0.6	16617
0.6-0.7	6322
0.7-0.8	942
0.8-0.85	52
0.85-0.9	20
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9725	High Similarity	NPC221275
0.9381	High Similarity	NPC254233
0.9182	High Similarity	NPC475002
0.9182	High Similarity	NPC95126
0.9035	High Similarity	NPC242764
0.9035	High Similarity	NPC105141
0.9035	High Similarity	NPC212891
0.8843	High Similarity	NPC253681
0.8818	High Similarity	NPC142326
0.8818	High Similarity	NPC94751
0.8761	High Similarity	NPC471188
0.876	High Similarity	NPC470765
0.875	High Similarity	NPC307139
0.8689	High Similarity	NPC5486
0.8689	High Similarity	NPC470753
0.8689	High Similarity	NPC473220
0.8618	High Similarity	NPC115797
0.8618	High Similarity	NPC51448
0.8607	High Similarity	NPC100402
0.8607	High Similarity	NPC9180
0.8583	High Similarity	NPC293831
0.8583	High Similarity	NPC369
0.8571	High Similarity	NPC183339
0.8571	High Similarity	NPC133389
0.8571	High Similarity	NPC234337
0.8559	High Similarity	NPC471186
0.8532	High Similarity	NPC136810
0.8532	High Similarity	NPC133809
0.8532	High Similarity	NPC225079
0.8532	High Similarity	NPC128248
0.8455	Intermediate Similarity	NPC275576
0.8443	Intermediate Similarity	NPC85511
0.8443	Intermediate Similarity	NPC77691
0.844	Intermediate Similarity	NPC221825
0.8407	Intermediate Similarity	NPC21929
0.8387	Intermediate Similarity	NPC169913
0.8378	Intermediate Similarity	NPC19856
0.8361	Intermediate Similarity	NPC273336
0.8361	Intermediate Similarity	NPC182333
0.8333	Intermediate Similarity	NPC131684
0.8306	Intermediate Similarity	NPC137416
0.8279	Intermediate Similarity	NPC167323
0.8279	Intermediate Similarity	NPC269923
0.8257	Intermediate Similarity	NPC226041
0.8226	Intermediate Similarity	NPC295664
0.822	Intermediate Similarity	NPC474095
0.8182	Intermediate Similarity	NPC202015
0.8125	Intermediate Similarity	NPC72915
0.812	Intermediate Similarity	NPC471189
0.8115	Intermediate Similarity	NPC238861
0.8115	Intermediate Similarity	NPC77000
0.8103	Intermediate Similarity	NPC273837
0.8087	Intermediate Similarity	NPC472979
0.8087	Intermediate Similarity	NPC27252
0.8077	Intermediate Similarity	NPC329913
0.8077	Intermediate Similarity	NPC126516
0.8077	Intermediate Similarity	NPC48929
0.8077	Intermediate Similarity	NPC203486
0.8067	Intermediate Similarity	NPC186933
0.8065	Intermediate Similarity	NPC121168
0.8051	Intermediate Similarity	NPC128368
0.8047	Intermediate Similarity	NPC147561
0.8036	Intermediate Similarity	NPC469481
0.8034	Intermediate Similarity	NPC133308
0.8033	Intermediate Similarity	NPC42657
0.8017	Intermediate Similarity	NPC475006
0.8015	Intermediate Similarity	NPC471864
0.8	Intermediate Similarity	NPC328107
0.7984	Intermediate Similarity	NPC162935
0.7984	Intermediate Similarity	NPC249340
0.7983	Intermediate Similarity	NPC471721
0.7967	Intermediate Similarity	NPC473243
0.7966	Intermediate Similarity	NPC66208
0.7955	Intermediate Similarity	NPC472551
0.7955	Intermediate Similarity	NPC472545
0.7937	Intermediate Similarity	NPC265413
0.7937	Intermediate Similarity	NPC10154
0.7931	Intermediate Similarity	NPC472980
0.7923	Intermediate Similarity	NPC258073
0.792	Intermediate Similarity	NPC472703
0.7913	Intermediate Similarity	NPC243601
0.791	Intermediate Similarity	NPC97667
0.791	Intermediate Similarity	NPC90614
0.791	Intermediate Similarity	NPC275592
0.791	Intermediate Similarity	NPC100913
0.791	Intermediate Similarity	NPC171207
0.7907	Intermediate Similarity	NPC82712
0.7907	Intermediate Similarity	NPC471832
0.7903	Intermediate Similarity	NPC241001
0.7903	Intermediate Similarity	NPC50872
0.7903	Intermediate Similarity	NPC472981
0.7899	Intermediate Similarity	NPC93287
0.7895	Intermediate Similarity	NPC39549
0.7895	Intermediate Similarity	NPC262324
0.7886	Intermediate Similarity	NPC204784
0.7881	Intermediate Similarity	NPC265513
0.7881	Intermediate Similarity	NPC210089
0.7879	Intermediate Similarity	NPC213122
0.7879	Intermediate Similarity	NPC477896
0.7879	Intermediate Similarity	NPC477893
0.7874	Intermediate Similarity	NPC470816
0.7869	Intermediate Similarity	NPC228318
0.7863	Intermediate Similarity	NPC472982
0.7863	Intermediate Similarity	NPC149455
0.7863	Intermediate Similarity	NPC469636
0.7863	Intermediate Similarity	NPC64642
0.7857	Intermediate Similarity	NPC12881
0.7857	Intermediate Similarity	NPC140118
0.7857	Intermediate Similarity	NPC473938
0.7857	Intermediate Similarity	NPC51079
0.7857	Intermediate Similarity	NPC472704
0.7852	Intermediate Similarity	NPC27377
0.7852	Intermediate Similarity	NPC87448
0.7852	Intermediate Similarity	NPC118080
0.7852	Intermediate Similarity	NPC472576
0.7852	Intermediate Similarity	NPC16912
0.7852	Intermediate Similarity	NPC97947
0.7852	Intermediate Similarity	NPC41481
0.7852	Intermediate Similarity	NPC291599
0.7852	Intermediate Similarity	NPC224491
0.7851	Intermediate Similarity	NPC135730
0.7851	Intermediate Similarity	NPC9274
0.7846	Intermediate Similarity	NPC249425
0.7846	Intermediate Similarity	NPC470278
0.7833	Intermediate Similarity	NPC153053
0.7826	Intermediate Similarity	NPC472222
0.7826	Intermediate Similarity	NPC472221
0.7823	Intermediate Similarity	NPC289432
0.7823	Intermediate Similarity	NPC232958
0.7823	Intermediate Similarity	NPC478121
0.7823	Intermediate Similarity	NPC988
0.782	Intermediate Similarity	NPC472372
0.782	Intermediate Similarity	NPC173569
0.782	Intermediate Similarity	NPC477874
0.782	Intermediate Similarity	NPC472374
0.7815	Intermediate Similarity	NPC270699
0.7815	Intermediate Similarity	NPC79496
0.7815	Intermediate Similarity	NPC82899
0.7815	Intermediate Similarity	NPC280789
0.7812	Intermediate Similarity	NPC171007
0.7812	Intermediate Similarity	NPC190849
0.7803	Intermediate Similarity	NPC474608
0.7803	Intermediate Similarity	NPC49742
0.7795	Intermediate Similarity	NPC111088
0.7778	Intermediate Similarity	NPC478058
0.7778	Intermediate Similarity	NPC265335
0.7778	Intermediate Similarity	NPC472547
0.7778	Intermediate Similarity	NPC79921
0.7778	Intermediate Similarity	NPC11250
0.7769	Intermediate Similarity	NPC306740
0.7769	Intermediate Similarity	NPC206028
0.7769	Intermediate Similarity	NPC228936
0.7769	Intermediate Similarity	NPC93181
0.7761	Intermediate Similarity	NPC243893
0.7761	Intermediate Similarity	NPC249817
0.776	Intermediate Similarity	NPC144547
0.7744	Intermediate Similarity	NPC212207
0.7744	Intermediate Similarity	NPC17877
0.7744	Intermediate Similarity	NPC195647
0.7744	Intermediate Similarity	NPC291638
0.7744	Intermediate Similarity	NPC66761
0.7744	Intermediate Similarity	NPC27394
0.7744	Intermediate Similarity	NPC472577
0.7737	Intermediate Similarity	NPC163087
0.7737	Intermediate Similarity	NPC477894
0.7737	Intermediate Similarity	NPC91703
0.7731	Intermediate Similarity	NPC474057
0.7731	Intermediate Similarity	NPC1082
0.7731	Intermediate Similarity	NPC305912
0.7727	Intermediate Similarity	NPC472656
0.7727	Intermediate Similarity	NPC165612
0.7724	Intermediate Similarity	NPC152812
0.7721	Intermediate Similarity	NPC471862
0.7719	Intermediate Similarity	NPC264728
0.7719	Intermediate Similarity	NPC245927
0.7717	Intermediate Similarity	NPC471187
0.7717	Intermediate Similarity	NPC318067
0.7712	Intermediate Similarity	NPC318327
0.771	Intermediate Similarity	NPC475102
0.7704	Intermediate Similarity	NPC22676
0.7704	Intermediate Similarity	NPC216940
0.7704	Intermediate Similarity	NPC475482
0.7704	Intermediate Similarity	NPC198621
0.7704	Intermediate Similarity	NPC471152
0.7698	Intermediate Similarity	NPC253627
0.7692	Intermediate Similarity	NPC225103
0.7687	Intermediate Similarity	NPC279463
0.7686	Intermediate Similarity	NPC196673
0.7686	Intermediate Similarity	NPC307651
0.7681	Intermediate Similarity	NPC95810
0.7681	Intermediate Similarity	NPC475759
0.7681	Intermediate Similarity	NPC70716
0.7681	Intermediate Similarity	NPC470152
0.7681	Intermediate Similarity	NPC472570
0.7681	Intermediate Similarity	NPC241951
0.7681	Intermediate Similarity	NPC475122
0.7681	Intermediate Similarity	NPC472569
0.7681	Intermediate Similarity	NPC11685
0.7681	Intermediate Similarity	NPC163719
0.7681	Intermediate Similarity	NPC95265

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 NPC45794 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	774
0.2-0.3	1102
0.3-0.4	2470
0.4-0.5	2468
0.5-0.6	1548
0.6-0.7	510
0.7-0.8	82
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.848	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD4198	Discontinued
0.8376	Intermediate Similarity	NPD5951	Approved
0.8333	Intermediate Similarity	NPD7008	Discontinued
0.8115	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD2629	Approved
0.7967	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD6663	Approved
0.7891	Intermediate Similarity	NPD5736	Approved
0.7805	Intermediate Similarity	NPD7741	Discontinued
0.7795	Intermediate Similarity	NPD1283	Approved
0.775	Intermediate Similarity	NPD6858	Approved
0.775	Intermediate Similarity	NPD7094	Approved
0.7731	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1088	Approved
0.7712	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD6010	Discontinued
0.7679	Intermediate Similarity	NPD1989	Approved
0.7672	Intermediate Similarity	NPD5909	Discontinued
0.7652	Intermediate Similarity	NPD8032	Phase 2
0.7632	Intermediate Similarity	NPD2066	Phase 3
0.7626	Intermediate Similarity	NPD7236	Approved
0.7609	Intermediate Similarity	NPD7003	Approved
0.7589	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD2182	Approved
0.7559	Intermediate Similarity	NPD1281	Approved
0.7545	Intermediate Similarity	NPD1090	Approved
0.7545	Intermediate Similarity	NPD1086	Approved
0.7545	Intermediate Similarity	NPD1089	Approved
0.754	Intermediate Similarity	NPD3019	Approved
0.7519	Intermediate Similarity	NPD7715	Approved
0.7519	Intermediate Similarity	NPD7714	Approved
0.7483	Intermediate Similarity	NPD7239	Suspended
0.7482	Intermediate Similarity	NPD8166	Discontinued
0.748	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD4140	Approved
0.7463	Intermediate Similarity	NPD2979	Phase 3
0.7455	Intermediate Similarity	NPD800	Approved
0.7436	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1929	Approved
0.7436	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1930	Approved
0.7434	Intermediate Similarity	NPD1693	Approved
0.7422	Intermediate Similarity	NPD4806	Approved
0.7422	Intermediate Similarity	NPD6287	Discontinued
0.7422	Intermediate Similarity	NPD4807	Approved
0.7405	Intermediate Similarity	NPD6085	Phase 2
0.7405	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD5126	Approved
0.7402	Intermediate Similarity	NPD5306	Approved
0.7402	Intermediate Similarity	NPD5125	Phase 3
0.7402	Intermediate Similarity	NPD5305	Approved
0.7402	Intermediate Similarity	NPD2932	Approved
0.7391	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6273	Approved
0.7328	Intermediate Similarity	NPD1238	Approved
0.7323	Intermediate Similarity	NPD1651	Approved
0.7321	Intermediate Similarity	NPD1239	Approved
0.7304	Intermediate Similarity	NPD1565	Approved
0.7304	Intermediate Similarity	NPD1564	Approved
0.7304	Intermediate Similarity	NPD1566	Phase 3
0.7295	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6049	Phase 2
0.7273	Intermediate Similarity	NPD1087	Approved
0.7259	Intermediate Similarity	NPD7961	Discontinued
0.7246	Intermediate Similarity	NPD7305	Phase 1
0.7239	Intermediate Similarity	NPD7095	Approved
0.7236	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD3673	Approved
0.7232	Intermediate Similarity	NPD3672	Approved
0.7227	Intermediate Similarity	NPD164	Approved
0.7213	Intermediate Similarity	NPD5236	Approved
0.7213	Intermediate Similarity	NPD5235	Approved
0.7213	Intermediate Similarity	NPD5239	Approved
0.7213	Intermediate Similarity	NPD5237	Approved
0.7213	Intermediate Similarity	NPD5240	Approved
0.7209	Intermediate Similarity	NPD3023	Approved
0.7209	Intermediate Similarity	NPD3026	Approved
0.7209	Intermediate Similarity	NPD4136	Approved
0.7209	Intermediate Similarity	NPD4106	Approved
0.7209	Intermediate Similarity	NPD4135	Approved
0.7197	Intermediate Similarity	NPD2797	Approved
0.7194	Intermediate Similarity	NPD2438	Suspended
0.7194	Intermediate Similarity	NPD2531	Phase 2
0.7194	Intermediate Similarity	NPD4476	Approved
0.7194	Intermediate Similarity	NPD4477	Approved
0.7193	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7458	Discontinued
0.7188	Intermediate Similarity	NPD3025	Approved
0.7188	Intermediate Similarity	NPD5691	Approved
0.7188	Intermediate Similarity	NPD5585	Approved
0.7188	Intermediate Similarity	NPD3024	Approved
0.7185	Intermediate Similarity	NPD3764	Approved
0.7179	Intermediate Similarity	NPD7798	Approved
0.7165	Intermediate Similarity	NPD7610	Discontinued
0.7153	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD3317	Approved
0.7143	Intermediate Similarity	NPD6647	Phase 2
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD5346	Phase 2
0.7143	Intermediate Similarity	NPD5347	Phase 2
0.7132	Intermediate Similarity	NPD4626	Approved
0.7132	Intermediate Similarity	NPD1778	Approved
0.7132	Intermediate Similarity	NPD4199	Phase 3
0.7121	Intermediate Similarity	NPD5667	Approved
0.7113	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1894	Discontinued
0.7099	Intermediate Similarity	NPD1608	Approved
0.7094	Intermediate Similarity	NPD9495	Approved
0.7075	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6099	Approved
0.7071	Intermediate Similarity	NPD6100	Approved
0.7063	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6798	Discontinued
0.7054	Intermediate Similarity	NPD4102	Approved
0.7054	Intermediate Similarity	NPD4105	Approved
0.7045	Intermediate Similarity	NPD5327	Phase 3
0.7043	Intermediate Similarity	NPD1563	Approved
0.7034	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6065	Approved
0.7023	Intermediate Similarity	NPD5618	Discontinued
0.7016	Intermediate Similarity	NPD2201	Approved
0.7015	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4624	Approved
0.7009	Intermediate Similarity	NPD3495	Discontinued
0.7007	Intermediate Similarity	NPD7713	Phase 3
0.6993	Remote Similarity	NPD4110	Phase 3
0.6993	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4628	Phase 3
0.6984	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2652	Approved
0.6984	Remote Similarity	NPD2650	Approved
0.6978	Remote Similarity	NPD6353	Approved
0.6977	Remote Similarity	NPD3091	Approved
0.697	Remote Similarity	NPD6637	Approved
0.6967	Remote Similarity	NPD6685	Approved
0.6964	Remote Similarity	NPD4793	Discontinued
0.6959	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4060	Phase 1
0.6939	Remote Similarity	NPD7427	Discontinued
0.6935	Remote Similarity	NPD2067	Discontinued
0.6935	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD3268	Approved
0.6929	Remote Similarity	NPD7097	Phase 1
0.6929	Remote Similarity	NPD4766	Approved
0.6917	Remote Similarity	NPD4359	Approved
0.6917	Remote Similarity	NPD1932	Approved
0.6912	Remote Similarity	NPD4620	Approved
0.6912	Remote Similarity	NPD7055	Discontinued
0.6912	Remote Similarity	NPD5201	Approved
0.6912	Remote Similarity	NPD4617	Approved
0.6912	Remote Similarity	NPD5203	Approved
0.6912	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD9491	Approved
0.6908	Remote Similarity	NPD7057	Phase 3
0.6908	Remote Similarity	NPD7058	Phase 2
0.6906	Remote Similarity	NPD5735	Approved
0.6905	Remote Similarity	NPD7635	Approved
0.6901	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5048	Discontinued
0.6884	Remote Similarity	NPD6233	Phase 2
0.6881	Remote Similarity	NPD226	Approved
0.6879	Remote Similarity	NPD2799	Discontinued
0.687	Remote Similarity	NPD17	Approved
0.687	Remote Similarity	NPD7725	Approved
0.687	Remote Similarity	NPD3095	Discontinued
0.686	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2329	Discontinued
0.6853	Remote Similarity	NPD4534	Discontinued
0.6846	Remote Similarity	NPD7009	Phase 2
0.6842	Remote Similarity	NPD3972	Approved
0.6838	Remote Similarity	NPD5204	Approved
0.6835	Remote Similarity	NPD5120	Approved
0.6835	Remote Similarity	NPD5121	Approved
0.6835	Remote Similarity	NPD5119	Approved
0.6818	Remote Similarity	NPD3847	Discontinued
0.6812	Remote Similarity	NPD2313	Discontinued
0.6812	Remote Similarity	NPD7985	Registered
0.6812	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5926	Approved
0.6806	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3047	Approved
0.6803	Remote Similarity	NPD3046	Approved
0.6803	Remote Similarity	NPD1237	Approved
0.6803	Remote Similarity	NPD3048	Approved
0.6788	Remote Similarity	NPD2614	Approved
0.6786	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5762	Approved
0.6783	Remote Similarity	NPD5763	Approved
0.6783	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6002	Phase 3
0.6783	Remote Similarity	NPD6005	Phase 3
0.6783	Remote Similarity	NPD6004	Phase 3
0.6774	Remote Similarity	NPD2342	Discontinued
0.6772	Remote Similarity	NPD5535	Approved
0.6769	Remote Similarity	NPD7644	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