NPASS Compound

Structure

NPC470257 OpenBabel07101719252D 39 42 0 0 1 0 0 0 0 0999 V2000 2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9855 2.6396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2424 3.3087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 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 -2.0032 1.9292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4164 4.2327 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 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 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 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 1.0563 2.5385 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0345 2.3305 0.0000 C 0 0 0 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 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3435 1.3795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2111 0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7473 3.4895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 9 39 1 0 0 0 0 10 11 1 0 0 0 0 10 16 2 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 18 2 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 14 28 1 0 0 0 0 15 22 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 30 1 6 0 0 0 18 25 1 0 0 0 0 18 32 1 0 0 0 0 19 24 1 0 0 0 0 19 33 1 1 0 0 0 20 28 1 1 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 21 34 2 0 0 0 0 22 30 1 0 0 0 0 22 35 2 0 0 0 0 23 13 1 6 0 0 0 23 27 1 0 0 0 0 23 39 1 0 0 0 0 24 29 1 6 0 0 0 24 31 1 0 0 0 0 25 26 1 0 0 0 0 25 36 2 0 0 0 0 27 37 1 0 0 0 0 28 29 1 1 0 0 0 29 6 1 6 0 0 0 30 7 1 6 0 0 0 31 8 1 6 0 0 0 31 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.32
Volume:	567.646
LogP:	2.344
LogD:	2.299
LogS:	-4.191
# Rotatable Bonds:	6
TPSA:	138.2
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.342
Synthetic Accessibility Score:	5.697
Fsp3:	0.806
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.053
MDCK Permeability:	1.641275048314128e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.056
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.729

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978
Plasma Protein Binding (PPB):	53.53999710083008%
Volume Distribution (VD):	0.399
Pgp-substrate:	27.02949333190918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.361
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.799
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.692
CYP3A4-substrate:	0.667

ADMET: Excretion

Clearance (CL):	5.97
Half-life (T1/2):	0.327

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.179
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.814
Maximum Recommended Daily Dose:	0.378
Skin Sensitization:	0.337
Carcinogencity:	0.768
Eye Corrosion:	0.004
Eye Irritation:	0.01
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC470257

Natural Product ID:	NPC470257
*Common Name:**	(8S,9R,10R,13R,14S,16R,17R)-17-[(2R,5S)-2,6-Dihydroxy-5-Methoxy-6-Methyl-3-Oxoheptan-2-Yl]-2,16-Dihydroxy-4,4,9,13,14-Pentamethyl-8,10,12,15,16,17-Hexahydro-7H-Cyclopenta[A]Phenanthrene-3,11-Dione
IUPAC Name:	(8S,9R,10R,13R,14S,16R,17R)-17-[(2R,5S)-2,6-dihydroxy-5-methoxy-6-methyl-3-oxoheptan-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
Synonyms:
Standard InCHIKey:	PRXKQJOTSWBYAZ-CJAZSQSXSA-N
Standard InCHI:	InChI=1S/C31H46O8/c1-26(2)16-10-11-20-28(5)14-19(33)24(31(8,38)21(34)13-23(39-9)27(3,4)37)29(28,6)15-22(35)30(20,7)17(16)12-18(32)25(26)36/h10,12,17,19-20,23-24,32-33,37-38H,11,13-15H2,1-9H3/t17-,19-,20+,23+,24+,28+,29-,30+,31+/m1/s1
SMILES:	CC1(C2=CCC3C4(CC(C(C4(CC(=O)C3(C2C=C(C1=O)O)C)C)C(C)(C(=O)CC(C(C)(C)O)OC)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923788
PubChem CID:	56833855
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO30742	Machilus yaoshansis	Species	Lauraceae	Eukaryota	root	Dayao Mountain, Guangxi, China	2007-DEC	PMID[22044245]
NPO30742	Machilus yaoshansis	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[22044245]
NPO30742	Machilus yaoshansis	Species	Lauraceae	Eukaryota	Roots	n.a.	n.a.	PMID[22779787]

☑ 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	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[534615]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[534615]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[534615]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[534615]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[534615]

☑ 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 NPC470257 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	211
0.1-0.2	1333
0.2-0.3	5077
0.3-0.4	9051
0.4-0.5	11996
0.5-0.6	7274
0.6-0.7	6046
0.7-0.8	1588
0.8-0.85	108
0.85-0.9	9
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC43285
0.98	High Similarity	NPC58370
0.92	High Similarity	NPC474720
0.9118	High Similarity	NPC117185
0.8868	High Similarity	NPC304495
0.885	High Similarity	NPC238005
0.885	High Similarity	NPC141196
0.885	High Similarity	NPC1980
0.8725	High Similarity	NPC147954
0.8696	High Similarity	NPC198714
0.8673	High Similarity	NPC42675
0.8611	High Similarity	NPC235077
0.8596	High Similarity	NPC216866
0.8571	High Similarity	NPC111323
0.8529	High Similarity	NPC49371
0.8426	Intermediate Similarity	NPC65941
0.8396	Intermediate Similarity	NPC191892
0.8378	Intermediate Similarity	NPC108721
0.8378	Intermediate Similarity	NPC73300
0.8376	Intermediate Similarity	NPC93368
0.8333	Intermediate Similarity	NPC319570
0.8333	Intermediate Similarity	NPC83744
0.8333	Intermediate Similarity	NPC165873
0.8319	Intermediate Similarity	NPC239273
0.8305	Intermediate Similarity	NPC152091
0.8304	Intermediate Similarity	NPC247069
0.8304	Intermediate Similarity	NPC473898
0.8302	Intermediate Similarity	NPC473928
0.8302	Intermediate Similarity	NPC87351
0.8291	Intermediate Similarity	NPC277191
0.8291	Intermediate Similarity	NPC473255
0.8291	Intermediate Similarity	NPC190846
0.8288	Intermediate Similarity	NPC221144
0.8288	Intermediate Similarity	NPC207251
0.8286	Intermediate Similarity	NPC144956
0.8269	Intermediate Similarity	NPC18509
0.8269	Intermediate Similarity	NPC27105
0.8257	Intermediate Similarity	NPC329417
0.8241	Intermediate Similarity	NPC471332
0.8241	Intermediate Similarity	NPC50692
0.8241	Intermediate Similarity	NPC152695
0.8241	Intermediate Similarity	NPC260268
0.8241	Intermediate Similarity	NPC476027
0.8241	Intermediate Similarity	NPC85829
0.8241	Intermediate Similarity	NPC171137
0.8241	Intermediate Similarity	NPC48733
0.8241	Intermediate Similarity	NPC319077
0.8241	Intermediate Similarity	NPC196528
0.8241	Intermediate Similarity	NPC471333
0.8241	Intermediate Similarity	NPC97202
0.8241	Intermediate Similarity	NPC202167
0.8241	Intermediate Similarity	NPC296945
0.8241	Intermediate Similarity	NPC49958
0.8241	Intermediate Similarity	NPC214264
0.8241	Intermediate Similarity	NPC302607
0.8241	Intermediate Similarity	NPC150531
0.8235	Intermediate Similarity	NPC474807
0.8224	Intermediate Similarity	NPC311612
0.8214	Intermediate Similarity	NPC250109
0.8214	Intermediate Similarity	NPC317210
0.8214	Intermediate Similarity	NPC194100
0.8198	Intermediate Similarity	NPC207689
0.819	Intermediate Similarity	NPC471331
0.819	Intermediate Similarity	NPC99657
0.819	Intermediate Similarity	NPC203388
0.819	Intermediate Similarity	NPC472687
0.819	Intermediate Similarity	NPC46570
0.819	Intermediate Similarity	NPC471330
0.8182	Intermediate Similarity	NPC241927
0.8182	Intermediate Similarity	NPC258543
0.8182	Intermediate Similarity	NPC214644
0.8182	Intermediate Similarity	NPC11710
0.8165	Intermediate Similarity	NPC477916
0.8165	Intermediate Similarity	NPC220229
0.8165	Intermediate Similarity	NPC475060
0.8151	Intermediate Similarity	NPC470882
0.8151	Intermediate Similarity	NPC473265
0.8148	Intermediate Similarity	NPC137657
0.8148	Intermediate Similarity	NPC255309
0.8148	Intermediate Similarity	NPC209502
0.8148	Intermediate Similarity	NPC204833
0.8148	Intermediate Similarity	NPC13385
0.8142	Intermediate Similarity	NPC326542
0.8131	Intermediate Similarity	NPC473424
0.8125	Intermediate Similarity	NPC170487
0.8125	Intermediate Similarity	NPC280782
0.812	Intermediate Similarity	NPC107493
0.8119	Intermediate Similarity	NPC326627
0.8119	Intermediate Similarity	NPC310010
0.8119	Intermediate Similarity	NPC477943
0.8099	Intermediate Similarity	NPC213634
0.8095	Intermediate Similarity	NPC472689
0.8095	Intermediate Similarity	NPC477268
0.8095	Intermediate Similarity	NPC477267
0.8095	Intermediate Similarity	NPC472690
0.8091	Intermediate Similarity	NPC217201
0.8077	Intermediate Similarity	NPC472932
0.8073	Intermediate Similarity	NPC96377
0.8073	Intermediate Similarity	NPC149047
0.807	Intermediate Similarity	NPC148458
0.8058	Intermediate Similarity	NPC233118
0.8056	Intermediate Similarity	NPC474207
0.8056	Intermediate Similarity	NPC474330
0.8053	Intermediate Similarity	NPC198539
0.8053	Intermediate Similarity	NPC962
0.8053	Intermediate Similarity	NPC52634
0.8037	Intermediate Similarity	NPC475867
0.8037	Intermediate Similarity	NPC270155
0.8037	Intermediate Similarity	NPC472924
0.8036	Intermediate Similarity	NPC214797
0.8036	Intermediate Similarity	NPC118860
0.8036	Intermediate Similarity	NPC472928
0.8036	Intermediate Similarity	NPC231589
0.8034	Intermediate Similarity	NPC471999
0.8034	Intermediate Similarity	NPC472000
0.802	Intermediate Similarity	NPC470417
0.8017	Intermediate Similarity	NPC473203
0.8017	Intermediate Similarity	NPC5292
0.8017	Intermediate Similarity	NPC472933
0.8017	Intermediate Similarity	NPC470880
0.8	Intermediate Similarity	NPC218970
0.8	Intermediate Similarity	NPC472934
0.8	Intermediate Similarity	NPC472734
0.8	Intermediate Similarity	NPC472925
0.8	Intermediate Similarity	NPC472733
0.8	Intermediate Similarity	NPC473253
0.8	Intermediate Similarity	NPC185
0.8	Intermediate Similarity	NPC471854
0.8	Intermediate Similarity	NPC44063
0.7983	Intermediate Similarity	NPC475194
0.7983	Intermediate Similarity	NPC6615
0.7983	Intermediate Similarity	NPC7850
0.7982	Intermediate Similarity	NPC75531
0.7982	Intermediate Similarity	NPC96268
0.7982	Intermediate Similarity	NPC235889
0.7982	Intermediate Similarity	NPC149124
0.7982	Intermediate Similarity	NPC471398
0.7981	Intermediate Similarity	NPC174051
0.7981	Intermediate Similarity	NPC67831
0.7981	Intermediate Similarity	NPC111015
0.7966	Intermediate Similarity	NPC222688
0.7966	Intermediate Similarity	NPC313528
0.7966	Intermediate Similarity	NPC269642
0.7965	Intermediate Similarity	NPC475524
0.7965	Intermediate Similarity	NPC100267
0.7965	Intermediate Similarity	NPC191620
0.7965	Intermediate Similarity	NPC71348
0.7963	Intermediate Similarity	NPC477915
0.7961	Intermediate Similarity	NPC19114
0.7949	Intermediate Similarity	NPC109973
0.7949	Intermediate Similarity	NPC79579
0.7946	Intermediate Similarity	NPC76084
0.7944	Intermediate Similarity	NPC154072
0.7944	Intermediate Similarity	NPC83709
0.7944	Intermediate Similarity	NPC167974
0.7944	Intermediate Similarity	NPC218383
0.7944	Intermediate Similarity	NPC15390
0.7934	Intermediate Similarity	NPC69273
0.7934	Intermediate Similarity	NPC168899
0.7934	Intermediate Similarity	NPC293623
0.7931	Intermediate Similarity	NPC257457
0.7931	Intermediate Similarity	NPC153440
0.7931	Intermediate Similarity	NPC311554
0.7925	Intermediate Similarity	NPC472731
0.7925	Intermediate Similarity	NPC273269
0.7925	Intermediate Similarity	NPC472732
0.7921	Intermediate Similarity	NPC90652
0.7913	Intermediate Similarity	NPC270958
0.7913	Intermediate Similarity	NPC49492
0.7913	Intermediate Similarity	NPC190286
0.7913	Intermediate Similarity	NPC31797
0.7913	Intermediate Similarity	NPC266728
0.7909	Intermediate Similarity	NPC181265
0.7909	Intermediate Similarity	NPC257353
0.7909	Intermediate Similarity	NPC475494
0.7909	Intermediate Similarity	NPC166607
0.7905	Intermediate Similarity	NPC263347
0.7905	Intermediate Similarity	NPC200702
0.7905	Intermediate Similarity	NPC472485
0.7905	Intermediate Similarity	NPC472824
0.7895	Intermediate Similarity	NPC477944
0.7895	Intermediate Similarity	NPC202889
0.7895	Intermediate Similarity	NPC472926
0.789	Intermediate Similarity	NPC236390
0.789	Intermediate Similarity	NPC159442
0.7885	Intermediate Similarity	NPC206810
0.7885	Intermediate Similarity	NPC472930
0.7881	Intermediate Similarity	NPC470921
0.7881	Intermediate Similarity	NPC472001
0.7876	Intermediate Similarity	NPC471243
0.7876	Intermediate Similarity	NPC472003
0.7876	Intermediate Similarity	NPC43775
0.7876	Intermediate Similarity	NPC474229
0.787	Intermediate Similarity	NPC471401
0.7869	Intermediate Similarity	NPC231529
0.7864	Intermediate Similarity	NPC171441
0.7864	Intermediate Similarity	NPC289213
0.7863	Intermediate Similarity	NPC470777
0.7863	Intermediate Similarity	NPC61520
0.7857	Intermediate Similarity	NPC471400

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 NPC470257 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1737
0.2-0.3	4100
0.3-0.4	2051
0.4-0.5	601
0.5-0.6	211
0.6-0.7	123
0.7-0.8	128
0.8-0.85	20
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8611	High Similarity	NPD4634	Approved
0.8421	Intermediate Similarity	NPD6319	Approved
0.8288	Intermediate Similarity	NPD8297	Approved
0.8286	Intermediate Similarity	NPD4696	Approved
0.8286	Intermediate Similarity	NPD5285	Approved
0.8286	Intermediate Similarity	NPD5286	Approved
0.8269	Intermediate Similarity	NPD4755	Approved
0.8261	Intermediate Similarity	NPD6054	Approved
0.8214	Intermediate Similarity	NPD4632	Approved
0.8198	Intermediate Similarity	NPD6649	Approved
0.8198	Intermediate Similarity	NPD6650	Approved
0.8182	Intermediate Similarity	NPD6373	Approved
0.8182	Intermediate Similarity	NPD6372	Approved
0.8131	Intermediate Similarity	NPD5211	Phase 2
0.8131	Intermediate Similarity	NPD5225	Approved
0.8131	Intermediate Similarity	NPD5224	Approved
0.8131	Intermediate Similarity	NPD5226	Approved
0.8131	Intermediate Similarity	NPD4633	Approved
0.812	Intermediate Similarity	NPD6370	Approved
0.8119	Intermediate Similarity	NPD4753	Phase 2
0.8113	Intermediate Similarity	NPD4700	Approved
0.8103	Intermediate Similarity	NPD6059	Approved
0.8091	Intermediate Similarity	NPD6899	Approved
0.8091	Intermediate Similarity	NPD6881	Approved
0.8077	Intermediate Similarity	NPD5210	Approved
0.8077	Intermediate Similarity	NPD4629	Approved
0.8073	Intermediate Similarity	NPD6402	Approved
0.8073	Intermediate Similarity	NPD7128	Approved
0.8073	Intermediate Similarity	NPD6675	Approved
0.8073	Intermediate Similarity	NPD5739	Approved
0.8056	Intermediate Similarity	NPD5174	Approved
0.8056	Intermediate Similarity	NPD5175	Approved
0.8037	Intermediate Similarity	NPD5223	Approved
0.8034	Intermediate Similarity	NPD6016	Approved
0.8034	Intermediate Similarity	NPD6015	Approved
0.8	Intermediate Similarity	NPD5697	Approved
0.7983	Intermediate Similarity	NPD7492	Approved
0.7982	Intermediate Similarity	NPD5141	Approved
0.7966	Intermediate Similarity	NPD5988	Approved
0.7965	Intermediate Similarity	NPD6882	Approved
0.7946	Intermediate Similarity	NPD7290	Approved
0.7946	Intermediate Similarity	NPD7102	Approved
0.7946	Intermediate Similarity	NPD6883	Approved
0.7928	Intermediate Similarity	NPD4730	Approved
0.7928	Intermediate Similarity	NPD7320	Approved
0.7928	Intermediate Similarity	NPD4729	Approved
0.7925	Intermediate Similarity	NPD6084	Phase 2
0.7925	Intermediate Similarity	NPD6083	Phase 2
0.7917	Intermediate Similarity	NPD6616	Approved
0.7909	Intermediate Similarity	NPD4768	Approved
0.7909	Intermediate Similarity	NPD4767	Approved
0.7905	Intermediate Similarity	NPD5695	Phase 3
0.7876	Intermediate Similarity	NPD6617	Approved
0.7876	Intermediate Similarity	NPD6869	Approved
0.7876	Intermediate Similarity	NPD6847	Approved
0.7876	Intermediate Similarity	NPD8130	Phase 1
0.7857	Intermediate Similarity	NPD6013	Approved
0.7857	Intermediate Similarity	NPD6014	Approved
0.7857	Intermediate Similarity	NPD6012	Approved
0.7851	Intermediate Similarity	NPD7078	Approved
0.7845	Intermediate Similarity	NPD6009	Approved
0.7838	Intermediate Similarity	NPD6412	Phase 2
0.7838	Intermediate Similarity	NPD5701	Approved
0.7822	Intermediate Similarity	NPD5690	Phase 2
0.7788	Intermediate Similarity	NPD5251	Approved
0.7788	Intermediate Similarity	NPD5250	Approved
0.7788	Intermediate Similarity	NPD5248	Approved
0.7788	Intermediate Similarity	NPD5247	Approved
0.7788	Intermediate Similarity	NPD5249	Phase 3
0.7787	Intermediate Similarity	NPD7736	Approved
0.7768	Intermediate Similarity	NPD5128	Approved
0.7768	Intermediate Similarity	NPD6011	Approved
0.7727	Intermediate Similarity	NPD4754	Approved
0.7723	Intermediate Similarity	NPD5329	Approved
0.7712	Intermediate Similarity	NPD4522	Approved
0.7705	Intermediate Similarity	NPD8293	Discontinued
0.7685	Intermediate Similarity	NPD5696	Approved
0.7664	Intermediate Similarity	NPD5221	Approved
0.7664	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD5222	Approved
0.7664	Intermediate Similarity	NPD4697	Phase 3
0.7647	Intermediate Similarity	NPD5280	Approved
0.7647	Intermediate Similarity	NPD5279	Phase 3
0.7647	Intermediate Similarity	NPD4694	Approved
0.7624	Intermediate Similarity	NPD3666	Approved
0.7624	Intermediate Similarity	NPD4197	Approved
0.7624	Intermediate Similarity	NPD3133	Approved
0.7624	Intermediate Similarity	NPD3665	Phase 1
0.7619	Intermediate Similarity	NPD6079	Approved
0.7603	Intermediate Similarity	NPD7604	Phase 2
0.7596	Intermediate Similarity	NPD5328	Approved
0.7593	Intermediate Similarity	NPD5173	Approved
0.7583	Intermediate Similarity	NPD5983	Phase 2
0.7565	Intermediate Similarity	NPD5217	Approved
0.7565	Intermediate Similarity	NPD5215	Approved
0.7565	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD5216	Approved
0.7547	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD6033	Approved
0.748	Intermediate Similarity	NPD6336	Discontinued
0.7478	Intermediate Similarity	NPD5135	Approved
0.7478	Intermediate Similarity	NPD5169	Approved
0.7478	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6274	Approved
0.7453	Intermediate Similarity	NPD5284	Approved
0.7453	Intermediate Similarity	NPD5281	Approved
0.7426	Intermediate Similarity	NPD4223	Phase 3
0.7426	Intermediate Similarity	NPD4221	Approved
0.7417	Intermediate Similarity	NPD7101	Approved
0.7417	Intermediate Similarity	NPD7100	Approved
0.7414	Intermediate Similarity	NPD5127	Approved
0.7395	Intermediate Similarity	NPD7115	Discovery
0.7353	Intermediate Similarity	NPD4788	Approved
0.7333	Intermediate Similarity	NPD6335	Approved
0.7317	Intermediate Similarity	NPD8328	Phase 3
0.7308	Intermediate Similarity	NPD3618	Phase 1
0.7302	Intermediate Similarity	NPD7319	Approved
0.729	Intermediate Similarity	NPD6050	Approved
0.7282	Intermediate Similarity	NPD4786	Approved
0.7281	Intermediate Similarity	NPD6008	Approved
0.7264	Intermediate Similarity	NPD6080	Approved
0.7264	Intermediate Similarity	NPD6904	Approved
0.7264	Intermediate Similarity	NPD6673	Approved
0.725	Intermediate Similarity	NPD6317	Approved
0.7244	Intermediate Similarity	NPD5956	Approved
0.7227	Intermediate Similarity	NPD5167	Approved
0.7222	Intermediate Similarity	NPD6399	Phase 3
0.7203	Intermediate Similarity	NPD6053	Discontinued
0.72	Intermediate Similarity	NPD7507	Approved
0.7196	Intermediate Similarity	NPD5692	Phase 3
0.719	Intermediate Similarity	NPD6313	Approved
0.719	Intermediate Similarity	NPD6314	Approved
0.717	Intermediate Similarity	NPD6672	Approved
0.717	Intermediate Similarity	NPD5737	Approved
0.7156	Intermediate Similarity	NPD5282	Discontinued
0.7154	Intermediate Similarity	NPD6909	Approved
0.7154	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6908	Approved
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD4690	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD4689	Approved
0.7143	Intermediate Similarity	NPD4693	Phase 3
0.7143	Intermediate Similarity	NPD5205	Approved
0.7143	Intermediate Similarity	NPD4138	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.7143	Intermediate Similarity	NPD4688	Approved
0.713	Intermediate Similarity	NPD5694	Approved
0.7087	Intermediate Similarity	NPD3667	Approved
0.7069	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5133	Approved
0.7059	Intermediate Similarity	NPD4695	Discontinued
0.7034	Intermediate Similarity	NPD6371	Approved
0.703	Intermediate Similarity	NPD3617	Approved
0.7018	Intermediate Similarity	NPD5091	Approved
0.7009	Intermediate Similarity	NPD6686	Approved
0.7009	Intermediate Similarity	NPD6903	Approved
0.7009	Intermediate Similarity	NPD5168	Approved
0.7009	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6098	Approved
0.6972	Remote Similarity	NPD5693	Phase 1
0.6961	Remote Similarity	NPD4195	Approved
0.6937	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7260	Phase 2
0.6885	Remote Similarity	NPD6868	Approved
0.6881	Remote Similarity	NPD5207	Approved
0.6881	Remote Similarity	NPD4096	Approved
0.688	Remote Similarity	NPD7503	Approved
0.6829	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD4692	Approved
0.6827	Remote Similarity	NPD4139	Approved
0.6818	Remote Similarity	NPD6411	Approved
0.6786	Remote Similarity	NPD5654	Approved
0.6754	Remote Similarity	NPD7638	Approved
0.6727	Remote Similarity	NPD5785	Approved
0.6697	Remote Similarity	NPD4518	Approved
0.6697	Remote Similarity	NPD5208	Approved
0.6696	Remote Similarity	NPD7640	Approved
0.6696	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD5959	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6067	Discontinued
0.664	Remote Similarity	NPD7327	Approved
0.664	Remote Similarity	NPD7328	Approved
0.6639	Remote Similarity	NPD6614	Approved
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD3668	Phase 3
0.6636	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6333	Approved
0.6618	Remote Similarity	NPD6334	Approved
0.6617	Remote Similarity	NPD6845	Suspended

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