NPASS Compound

Structure

NPC476253 OpenBabel07101719252D 34 38 0 0 1 0 0 0 0 0999 V2000 -0.6704 -0.9035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5092 0.6322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3909 1.8009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8909 0.9349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7928 2.3009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4730 1.1099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9213 -0.3036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6589 -0.1991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5249 0.3009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7244 -1.2818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9268 1.8009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5249 3.3009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6589 2.8009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7189 -1.1773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0608 1.3009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0305 0.7907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8812 1.3570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3395 -0.1603 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5106 0.5799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3176 -0.3683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7928 1.3009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7928 0.3009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5249 1.3009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3909 2.8009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3909 1.8009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6589 1.8009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0608 0.3009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9268 -0.1991 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0523 0.9986 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -8.2569 3.3009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3243 -1.1924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0615 1.9986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 14 1 0 0 0 0 10 20 2 0 0 0 0 11 15 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 28 1 0 0 0 0 16 18 1 0 0 0 0 16 30 1 0 0 0 0 17 19 2 0 0 0 0 17 30 1 0 0 0 0 18 1 1 1 0 0 0 18 20 1 0 0 0 0 19 25 1 0 0 0 0 20 28 1 0 0 0 0 21 22 2 0 0 0 0 21 27 1 0 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 23 27 1 1 0 0 0 24 26 1 0 0 0 0 24 31 2 0 0 0 0 25 32 2 0 0 0 0 25 34 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 6 0 0 0 30 33 1 0 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.31
Volume:	506.632
LogP:	4.912
LogD:	3.486
LogS:	-5.167
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.384
Synthetic Accessibility Score:	5.23
Fsp3:	0.733
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:	-4.978
MDCK Permeability:	1.756331585056614e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.801
30% Bioavailability (F30%):	0.233

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.339
Plasma Protein Binding (PPB):	93.14387512207031%
Volume Distribution (VD):	1.559
Pgp-substrate:	3.8410167694091797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.667
CYP2C19-inhibitor:	0.674
CYP2C19-substrate:	0.957
CYP2C9-inhibitor:	0.632
CYP2C9-substrate:	0.589
CYP2D6-inhibitor:	0.479
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	7.063
Half-life (T1/2):	0.341

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.079
Carcinogencity:	0.498
Eye Corrosion:	0.004
Eye Irritation:	0.406
Respiratory Toxicity:	0.776

Download Data

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

Natural Product: NPC476253

Natural Product ID:	NPC476253
*Common Name:**	Neoabieslactone E
IUPAC Name:	5-hydroxy-3-methyl-5-[(2R)-2-[(5R,10S,13R,14S)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15-octahydrocyclopenta[a]phenanthren-17-yl]propyl]furan-2-one
Synonyms:	neoabieslactone E
Standard InCHIKey:	WEQIMNLYAOTTFY-BPECNVHGSA-N
Standard InCHI:	InChI=1S/C30H42O4/c1-18(16-30(33)17-19(2)25(32)34-30)20-10-14-29(7)22-8-9-23-26(3,4)24(31)12-13-27(23,5)21(22)11-15-28(20,29)6/h10,17-18,23,33H,8-9,11-16H2,1-7H3/t18-,23+,27-,28-,29+,30?/m1/s1
SMILES:	CC1=CC(OC1=O)(CC(C)C2=CCC3(C2(CCC4=C3CCC5C4(CCC(=O)C5(C)C)C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558635
PubChem CID:	44179575
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

*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
NPO6329	Abies chensiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19435338]
NPO33399	abies faxoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25554367]
NPO6329	Abies chensiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31557016]
NPO6329	Abies chensiensis	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
IC50	6

Activity Type	# Activity
Cell Line	4
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	=	9.1	ug.mL-1	PMID[481655]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	20.0	ug.mL-1	PMID[481655]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	16700.0	nM	PMID[481656]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	13400.0	nM	PMID[481656]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	20900.0	nM	PMID[481656]
NPT27	Others	Unspecified		IC50	=	10100.0	nM	PMID[481656]

☑ 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 NPC476253 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	188
0.1-0.2	1113
0.2-0.3	4479
0.3-0.4	11099
0.4-0.5	12510
0.5-0.6	7161
0.6-0.7	4902
0.7-0.8	1149
0.8-0.85	88
0.85-0.9	6
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8737	High Similarity	NPC171395
0.8667	High Similarity	NPC472865
0.8617	High Similarity	NPC289479
0.8602	High Similarity	NPC5509
0.8526	High Similarity	NPC472303
0.8526	High Similarity	NPC472871
0.8511	High Similarity	NPC472866
0.8495	Intermediate Similarity	NPC472870
0.8478	Intermediate Similarity	NPC472869
0.8462	Intermediate Similarity	NPC472864
0.8462	Intermediate Similarity	NPC19849
0.8462	Intermediate Similarity	NPC164577
0.8454	Intermediate Similarity	NPC470801
0.8421	Intermediate Similarity	NPC204341
0.8404	Intermediate Similarity	NPC262043
0.8387	Intermediate Similarity	NPC136948
0.837	Intermediate Similarity	NPC189311
0.8352	Intermediate Similarity	NPC97913
0.8352	Intermediate Similarity	NPC49019
0.835	Intermediate Similarity	NPC220155
0.8316	Intermediate Similarity	NPC281942
0.8316	Intermediate Similarity	NPC232426
0.83	Intermediate Similarity	NPC99411
0.8265	Intermediate Similarity	NPC472941
0.8265	Intermediate Similarity	NPC456
0.8261	Intermediate Similarity	NPC248758
0.8261	Intermediate Similarity	NPC475100
0.8252	Intermediate Similarity	NPC91034
0.8242	Intermediate Similarity	NPC3511
0.8242	Intermediate Similarity	NPC472867
0.8242	Intermediate Similarity	NPC142253
0.8235	Intermediate Similarity	NPC472868
0.8229	Intermediate Similarity	NPC141831
0.8229	Intermediate Similarity	NPC477783
0.8211	Intermediate Similarity	NPC174342
0.8211	Intermediate Similarity	NPC285982
0.82	Intermediate Similarity	NPC201406
0.819	Intermediate Similarity	NPC29133
0.8182	Intermediate Similarity	NPC253826
0.8172	Intermediate Similarity	NPC65661
0.8172	Intermediate Similarity	NPC29447
0.8172	Intermediate Similarity	NPC8571
0.8163	Intermediate Similarity	NPC293052
0.8155	Intermediate Similarity	NPC127790
0.8152	Intermediate Similarity	NPC470015
0.8152	Intermediate Similarity	NPC168188
0.8144	Intermediate Similarity	NPC115021
0.8137	Intermediate Similarity	NPC112009
0.8137	Intermediate Similarity	NPC180204
0.8132	Intermediate Similarity	NPC38350
0.8132	Intermediate Similarity	NPC477372
0.8132	Intermediate Similarity	NPC201912
0.8132	Intermediate Similarity	NPC278459
0.8125	Intermediate Similarity	NPC477149
0.8125	Intermediate Similarity	NPC477147
0.8125	Intermediate Similarity	NPC51486
0.8125	Intermediate Similarity	NPC476437
0.8125	Intermediate Similarity	NPC476369
0.8125	Intermediate Similarity	NPC477782
0.8113	Intermediate Similarity	NPC470961
0.8105	Intermediate Similarity	NPC226863
0.8105	Intermediate Similarity	NPC72397
0.8105	Intermediate Similarity	NPC117122
0.81	Intermediate Similarity	NPC197386
0.81	Intermediate Similarity	NPC235464
0.81	Intermediate Similarity	NPC166745
0.81	Intermediate Similarity	NPC471717
0.81	Intermediate Similarity	NPC98868
0.8085	Intermediate Similarity	NPC186975
0.8081	Intermediate Similarity	NPC190713
0.8081	Intermediate Similarity	NPC328371
0.8065	Intermediate Similarity	NPC87552
0.8061	Intermediate Similarity	NPC53685
0.8061	Intermediate Similarity	NPC184870
0.8061	Intermediate Similarity	NPC476415
0.8058	Intermediate Similarity	NPC189616
0.8043	Intermediate Similarity	NPC260956
0.8043	Intermediate Similarity	NPC320514
0.8043	Intermediate Similarity	NPC472239
0.8041	Intermediate Similarity	NPC473986
0.8041	Intermediate Similarity	NPC165904
0.8041	Intermediate Similarity	NPC179517
0.8041	Intermediate Similarity	NPC474018
0.8041	Intermediate Similarity	NPC470113
0.8039	Intermediate Similarity	NPC475320
0.8021	Intermediate Similarity	NPC214387
0.8021	Intermediate Similarity	NPC251528
0.8021	Intermediate Similarity	NPC66344
0.802	Intermediate Similarity	NPC476274
0.802	Intermediate Similarity	NPC477720
0.802	Intermediate Similarity	NPC476767
0.802	Intermediate Similarity	NPC287833
0.8019	Intermediate Similarity	NPC37116
0.8	Intermediate Similarity	NPC475709
0.8	Intermediate Similarity	NPC312561
0.8	Intermediate Similarity	NPC475894
0.8	Intermediate Similarity	NPC475913
0.8	Intermediate Similarity	NPC208094
0.8	Intermediate Similarity	NPC476409
0.8	Intermediate Similarity	NPC74410
0.8	Intermediate Similarity	NPC236618
0.798	Intermediate Similarity	NPC318282
0.798	Intermediate Similarity	NPC476174
0.798	Intermediate Similarity	NPC174948
0.798	Intermediate Similarity	NPC127197
0.798	Intermediate Similarity	NPC295347
0.798	Intermediate Similarity	NPC173875
0.798	Intermediate Similarity	NPC469995
0.7979	Intermediate Similarity	NPC106416
0.7979	Intermediate Similarity	NPC475860
0.7979	Intermediate Similarity	NPC86316
0.7979	Intermediate Similarity	NPC311702
0.7979	Intermediate Similarity	NPC473659
0.7979	Intermediate Similarity	NPC123319
0.7979	Intermediate Similarity	NPC94531
0.7979	Intermediate Similarity	NPC474694
0.7959	Intermediate Similarity	NPC476416
0.7959	Intermediate Similarity	NPC229976
0.7957	Intermediate Similarity	NPC83569
0.7957	Intermediate Similarity	NPC69279
0.7941	Intermediate Similarity	NPC224720
0.7941	Intermediate Similarity	NPC472643
0.7941	Intermediate Similarity	NPC476240
0.7941	Intermediate Similarity	NPC63249
0.7941	Intermediate Similarity	NPC476223
0.7941	Intermediate Similarity	NPC472924
0.7935	Intermediate Similarity	NPC147066
0.7935	Intermediate Similarity	NPC40228
0.7928	Intermediate Similarity	NPC474179
0.7928	Intermediate Similarity	NPC475834
0.7921	Intermediate Similarity	NPC92275
0.7921	Intermediate Similarity	NPC478056
0.7917	Intermediate Similarity	NPC48107
0.7917	Intermediate Similarity	NPC472302
0.7917	Intermediate Similarity	NPC24816
0.7912	Intermediate Similarity	NPC477371
0.7905	Intermediate Similarity	NPC475294
0.79	Intermediate Similarity	NPC29152
0.79	Intermediate Similarity	NPC7124
0.7895	Intermediate Similarity	NPC474062
0.789	Intermediate Similarity	NPC474181
0.7889	Intermediate Similarity	NPC97377
0.7879	Intermediate Similarity	NPC104925
0.7879	Intermediate Similarity	NPC298973
0.7879	Intermediate Similarity	NPC474554
0.7872	Intermediate Similarity	NPC474693
0.787	Intermediate Similarity	NPC191620
0.787	Intermediate Similarity	NPC236217
0.7864	Intermediate Similarity	NPC293753
0.7864	Intermediate Similarity	NPC476769
0.7864	Intermediate Similarity	NPC134077
0.7857	Intermediate Similarity	NPC190442
0.7857	Intermediate Similarity	NPC472814
0.7857	Intermediate Similarity	NPC329842
0.7857	Intermediate Similarity	NPC177037
0.785	Intermediate Similarity	NPC473627
0.7849	Intermediate Similarity	NPC321289
0.7849	Intermediate Similarity	NPC200513
0.7849	Intermediate Similarity	NPC133391
0.7849	Intermediate Similarity	NPC327969
0.7843	Intermediate Similarity	NPC51370
0.7843	Intermediate Similarity	NPC472644
0.7843	Intermediate Similarity	NPC241221
0.7843	Intermediate Similarity	NPC474012
0.7843	Intermediate Similarity	NPC471041
0.7843	Intermediate Similarity	NPC476299
0.7843	Intermediate Similarity	NPC54705
0.7835	Intermediate Similarity	NPC168131
0.7835	Intermediate Similarity	NPC470734
0.7835	Intermediate Similarity	NPC474570
0.7835	Intermediate Similarity	NPC177141
0.783	Intermediate Similarity	NPC61411
0.7822	Intermediate Similarity	NPC121339
0.7822	Intermediate Similarity	NPC53844
0.7822	Intermediate Similarity	NPC202705
0.7822	Intermediate Similarity	NPC156546
0.7822	Intermediate Similarity	NPC320306
0.7818	Intermediate Similarity	NPC176840
0.7812	Intermediate Similarity	NPC477228
0.7812	Intermediate Similarity	NPC128644
0.7812	Intermediate Similarity	NPC171722
0.7812	Intermediate Similarity	NPC167877
0.781	Intermediate Similarity	NPC472935
0.7802	Intermediate Similarity	NPC198240
0.78	Intermediate Similarity	NPC209355
0.78	Intermediate Similarity	NPC33473
0.7789	Intermediate Similarity	NPC473038
0.7789	Intermediate Similarity	NPC471300
0.7789	Intermediate Similarity	NPC11711
0.7789	Intermediate Similarity	NPC474860
0.7789	Intermediate Similarity	NPC474537
0.7789	Intermediate Similarity	NPC473251
0.7789	Intermediate Similarity	NPC42586
0.7789	Intermediate Similarity	NPC474083
0.7789	Intermediate Similarity	NPC60350
0.7789	Intermediate Similarity	NPC269638
0.7788	Intermediate Similarity	NPC236390
0.7788	Intermediate Similarity	NPC470418
0.7788	Intermediate Similarity	NPC476237
0.7778	Intermediate Similarity	NPC475657

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 NPC476253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1434
0.2-0.3	3759
0.3-0.4	2556
0.4-0.5	762
0.5-0.6	277
0.6-0.7	161
0.7-0.8	29
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7857	Intermediate Similarity	NPD5693	Phase 1
0.7849	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD5695	Phase 3
0.7732	Intermediate Similarity	NPD6672	Approved
0.7732	Intermediate Similarity	NPD5737	Approved
0.7677	Intermediate Similarity	NPD6050	Approved
0.7677	Intermediate Similarity	NPD5281	Approved
0.7677	Intermediate Similarity	NPD5284	Approved
0.7653	Intermediate Similarity	NPD6904	Approved
0.7653	Intermediate Similarity	NPD6673	Approved
0.7653	Intermediate Similarity	NPD6080	Approved
0.7647	Intermediate Similarity	NPD6083	Phase 2
0.7647	Intermediate Similarity	NPD6084	Phase 2
0.76	Intermediate Similarity	NPD6399	Phase 3
0.7576	Intermediate Similarity	NPD5692	Phase 3
0.7576	Intermediate Similarity	NPD5207	Approved
0.7551	Intermediate Similarity	NPD6903	Approved
0.7526	Intermediate Similarity	NPD6684	Approved
0.7526	Intermediate Similarity	NPD4623	Approved
0.7526	Intermediate Similarity	NPD5690	Phase 2
0.7526	Intermediate Similarity	NPD7334	Approved
0.7526	Intermediate Similarity	NPD5330	Approved
0.7526	Intermediate Similarity	NPD4519	Discontinued
0.7526	Intermediate Similarity	NPD6409	Approved
0.7526	Intermediate Similarity	NPD7146	Approved
0.7526	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD6404	Discontinued
0.75	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD5694	Approved
0.75	Intermediate Similarity	NPD6686	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.7474	Intermediate Similarity	NPD4221	Approved
0.7474	Intermediate Similarity	NPD4223	Phase 3
0.7451	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7115	Discovery
0.7423	Intermediate Similarity	NPD5329	Approved
0.7404	Intermediate Similarity	NPD5696	Approved
0.7404	Intermediate Similarity	NPD7638	Approved
0.7374	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5208	Approved
0.7353	Intermediate Similarity	NPD7748	Approved
0.7347	Intermediate Similarity	NPD6098	Approved
0.7347	Intermediate Similarity	NPD4694	Approved
0.7347	Intermediate Similarity	NPD5280	Approved
0.732	Intermediate Similarity	NPD4197	Approved
0.73	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4695	Discontinued
0.7245	Intermediate Similarity	NPD1694	Approved
0.7232	Intermediate Similarity	NPD6882	Approved
0.7184	Intermediate Similarity	NPD6001	Approved
0.7182	Intermediate Similarity	NPD7320	Approved
0.7182	Intermediate Similarity	NPD6881	Approved
0.7182	Intermediate Similarity	NPD6899	Approved
0.7172	Intermediate Similarity	NPD4688	Approved
0.7172	Intermediate Similarity	NPD5279	Phase 3
0.7172	Intermediate Similarity	NPD4689	Approved
0.7172	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4690	Approved
0.7172	Intermediate Similarity	NPD5205	Approved
0.7172	Intermediate Similarity	NPD4138	Approved
0.7172	Intermediate Similarity	NPD4693	Phase 3
0.7157	Intermediate Similarity	NPD7515	Phase 2
0.7157	Intermediate Similarity	NPD6079	Approved
0.7156	Intermediate Similarity	NPD7128	Approved
0.7156	Intermediate Similarity	NPD5739	Approved
0.7156	Intermediate Similarity	NPD6675	Approved
0.7156	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD4786	Approved
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD3666	Approved
0.7129	Intermediate Similarity	NPD5328	Approved
0.7129	Intermediate Similarity	NPD4753	Phase 2
0.7115	Intermediate Similarity	NPD5654	Approved
0.71	Intermediate Similarity	NPD3573	Approved
0.7091	Intermediate Similarity	NPD5697	Approved
0.7059	Intermediate Similarity	NPD5785	Approved
0.7054	Intermediate Similarity	NPD7290	Approved
0.7054	Intermediate Similarity	NPD7102	Approved
0.7054	Intermediate Similarity	NPD6883	Approved
0.7053	Intermediate Similarity	NPD3617	Approved
0.7048	Intermediate Similarity	NPD7614	Phase 1
0.7027	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD3618	Phase 1
0.6991	Remote Similarity	NPD6847	Approved
0.6991	Remote Similarity	NPD6650	Approved
0.6991	Remote Similarity	NPD6617	Approved
0.6991	Remote Similarity	NPD6869	Approved
0.6991	Remote Similarity	NPD6649	Approved
0.6991	Remote Similarity	NPD8130	Phase 1
0.6989	Remote Similarity	NPD5733	Approved
0.6981	Remote Similarity	NPD5959	Approved
0.6979	Remote Similarity	NPD4195	Approved
0.6972	Remote Similarity	NPD6052	Approved
0.697	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6372	Approved
0.6964	Remote Similarity	NPD6014	Approved
0.6964	Remote Similarity	NPD6012	Approved
0.6964	Remote Similarity	NPD6373	Approved
0.6964	Remote Similarity	NPD6013	Approved
0.6961	Remote Similarity	NPD6051	Approved
0.6952	Remote Similarity	NPD5210	Approved
0.6952	Remote Similarity	NPD4629	Approved
0.6942	Remote Similarity	NPD7507	Approved
0.6939	Remote Similarity	NPD3667	Approved
0.6937	Remote Similarity	NPD6412	Phase 2
0.6937	Remote Similarity	NPD5701	Approved
0.693	Remote Similarity	NPD8297	Approved
0.693	Remote Similarity	NPD6053	Discontinued
0.6916	Remote Similarity	NPD4225	Approved
0.6893	Remote Similarity	NPD4096	Approved
0.6887	Remote Similarity	NPD5222	Approved
0.6887	Remote Similarity	NPD5221	Approved
0.6887	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5211	Phase 2
0.6881	Remote Similarity	NPD7632	Discontinued
0.6875	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5362	Discontinued
0.6857	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7900	Approved
0.6848	Remote Similarity	NPD4747	Approved
0.6848	Remote Similarity	NPD4691	Approved
0.6842	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4692	Approved
0.6837	Remote Similarity	NPD4139	Approved
0.6822	Remote Similarity	NPD5173	Approved
0.6809	Remote Similarity	NPD4687	Approved
0.6792	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6614	Approved
0.6774	Remote Similarity	NPD7319	Approved
0.6774	Remote Similarity	NPD5276	Approved
0.6762	Remote Similarity	NPD4202	Approved
0.6762	Remote Similarity	NPD5133	Approved
0.6757	Remote Similarity	NPD5141	Approved
0.6752	Remote Similarity	NPD6868	Approved
0.6739	Remote Similarity	NPD4137	Phase 3
0.6729	Remote Similarity	NPD7732	Phase 3
0.6729	Remote Similarity	NPD4697	Phase 3
0.6721	Remote Similarity	NPD7492	Approved
0.67	Remote Similarity	NPD4788	Approved
0.6699	Remote Similarity	NPD4518	Approved
0.6697	Remote Similarity	NPD5286	Approved
0.6697	Remote Similarity	NPD5285	Approved
0.6697	Remote Similarity	NPD4696	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6695	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7328	Approved
0.6639	Remote Similarity	NPD7327	Approved
0.6639	Remote Similarity	NPD6335	Approved
0.6636	Remote Similarity	NPD5223	Approved
0.6634	Remote Similarity	NPD3668	Phase 3
0.6632	Remote Similarity	NPD4058	Approved
0.6613	Remote Similarity	NPD7078	Approved
0.661	Remote Similarity	NPD6274	Approved
0.6609	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6371	Approved
0.6604	Remote Similarity	NPD5778	Approved
0.6604	Remote Similarity	NPD5779	Approved
0.6583	Remote Similarity	NPD7100	Approved
0.6583	Remote Similarity	NPD7516	Approved
0.6583	Remote Similarity	NPD7101	Approved
0.6581	Remote Similarity	NPD4632	Approved
0.6577	Remote Similarity	NPD4633	Approved
0.6577	Remote Similarity	NPD5091	Approved
0.6577	Remote Similarity	NPD5226	Approved
0.6577	Remote Similarity	NPD5225	Approved
0.6577	Remote Similarity	NPD5224	Approved
0.6569	Remote Similarity	NPD5363	Approved
0.6569	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8039	Approved
0.656	Remote Similarity	NPD7736	Approved
0.6557	Remote Similarity	NPD6370	Approved
0.6555	Remote Similarity	NPD6317	Approved
0.6545	Remote Similarity	NPD4700	Approved
0.6535	Remote Similarity	NPD7154	Phase 3
0.6529	Remote Similarity	NPD8377	Approved
0.6529	Remote Similarity	NPD6059	Approved
0.6529	Remote Similarity	NPD8294	Approved
0.6518	Remote Similarity	NPD5174	Approved
0.6518	Remote Similarity	NPD5175	Approved
0.6509	Remote Similarity	NPD7637	Suspended
0.65	Remote Similarity	NPD6313	Approved
0.65	Remote Similarity	NPD6314	Approved
0.648	Remote Similarity	NPD8293	Discontinued
0.6476	Remote Similarity	NPD6101	Approved
0.6476	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8379	Approved
0.6475	Remote Similarity	NPD6016	Approved
0.6475	Remote Similarity	NPD8378	Approved
0.6475	Remote Similarity	NPD6015	Approved
0.6475	Remote Similarity	NPD8296	Approved
0.6475	Remote Similarity	NPD6291	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