NPASS Compound

Structure

NPC58370 OpenBabel07101718302D 38 41 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 1.7321 -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 1.0563 2.5385 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 -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 0.7473 3.4895 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 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 17 2 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 27 1 0 0 0 0 14 22 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 29 1 6 0 0 0 17 24 1 0 0 0 0 17 31 1 0 0 0 0 18 23 1 0 0 0 0 18 32 1 1 0 0 0 19 27 1 1 0 0 0 19 29 1 0 0 0 0 20 26 1 0 0 0 0 20 33 1 6 0 0 0 21 30 1 0 0 0 0 21 34 2 0 0 0 0 22 29 1 0 0 0 0 22 35 2 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 36 2 0 0 0 0 26 37 1 0 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 30 8 1 6 0 0 0 30 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.3
Volume:	550.35
LogP:	2.121
LogD:	1.835
LogS:	-4.422
# Rotatable Bonds:	5
TPSA:	149.2
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.394
Synthetic Accessibility Score:	5.442
Fsp3:	0.8
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:	-5.074
MDCK Permeability:	1.2661097571253777e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.469
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.271
30% Bioavailability (F30%):	0.931

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	76.81531524658203%
Volume Distribution (VD):	0.435
Pgp-substrate:	17.055198669433594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.211
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.804
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.655
CYP3A4-substrate:	0.576

ADMET: Excretion

Clearance (CL):	4.001
Half-life (T1/2):	0.599

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.91
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.317
Carcinogencity:	0.784
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC58370

Natural Product ID:	NPC58370
*Common Name:**	(8S,9R,10R,13R,14S,16R,17R)-2,16-Dihydroxy-4,4,9,13,14-Pentamethyl-17-[(2R,5S)-2,5,6-Trihydroxy-6-Methyl-3-Oxoheptan-2-Yl]-8,10,12,15,16,17-Hexahydro-7H-Cyclopenta[A]Phenanthrene-3,11-Dione
IUPAC Name:	(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-17-[(2R,5S)-2,5,6-trihydroxy-6-methyl-3-oxoheptan-2-yl]-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
Synonyms:
Standard InCHIKey:	FBGLZDYMEULGSX-TVAWUZSASA-N
Standard InCHI:	InChI=1S/C30H44O8/c1-25(2)15-9-10-19-27(5)13-18(32)23(30(8,38)21(34)12-20(33)26(3,4)37)28(27,6)14-22(35)29(19,7)16(15)11-17(31)24(25)36/h9,11,16,18-20,23,31-33,37-38H,10,12-14H2,1-8H3/t16-,18-,19+,20+,23+,27+,28-,29+,30+/m1/s1
SMILES:	CC1(C)C2=CC[C@H]3[C@]4(C)C[C@H]([C@@H]([C@@]4(C)CC(=O)[C@@]3(C)[C@@H]2C=C(C1=O)O)[C@](C)(C(=O)C[C@@H](C(C)(C)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923789
PubChem CID:	57402770
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[572915]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[572915]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[572915]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[572915]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[572915]

☑ 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 NPC58370 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	209
0.1-0.2	1347
0.2-0.3	5360
0.3-0.4	9599
0.4-0.5	11642
0.5-0.6	7425
0.6-0.7	5586
0.7-0.8	1414
0.8-0.85	100
0.85-0.9	10
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC43285
0.98	High Similarity	NPC470257
0.9388	High Similarity	NPC474720
0.93	High Similarity	NPC117185
0.89	High Similarity	NPC147954
0.8857	High Similarity	NPC304495
0.8774	High Similarity	NPC235077
0.8738	High Similarity	NPC111323
0.87	High Similarity	NPC49371
0.8673	High Similarity	NPC1980
0.8673	High Similarity	NPC238005
0.8673	High Similarity	NPC141196
0.8585	High Similarity	NPC65941
0.8558	High Similarity	NPC191892
0.8532	High Similarity	NPC108721
0.8532	High Similarity	NPC73300
0.8522	High Similarity	NPC198714
0.8496	Intermediate Similarity	NPC42675
0.8491	Intermediate Similarity	NPC165873
0.8491	Intermediate Similarity	NPC83744
0.8462	Intermediate Similarity	NPC87351
0.8447	Intermediate Similarity	NPC144956
0.8431	Intermediate Similarity	NPC18509
0.8421	Intermediate Similarity	NPC216866
0.8411	Intermediate Similarity	NPC329417
0.84	Intermediate Similarity	NPC474807
0.8396	Intermediate Similarity	NPC202167
0.8396	Intermediate Similarity	NPC48733
0.8396	Intermediate Similarity	NPC97202
0.8396	Intermediate Similarity	NPC296945
0.8396	Intermediate Similarity	NPC214264
0.8396	Intermediate Similarity	NPC302607
0.8396	Intermediate Similarity	NPC150531
0.8396	Intermediate Similarity	NPC319077
0.8396	Intermediate Similarity	NPC260268
0.8396	Intermediate Similarity	NPC152695
0.8396	Intermediate Similarity	NPC476027
0.8396	Intermediate Similarity	NPC49958
0.8396	Intermediate Similarity	NPC50692
0.8396	Intermediate Similarity	NPC85829
0.8396	Intermediate Similarity	NPC171137
0.8381	Intermediate Similarity	NPC311612
0.8333	Intermediate Similarity	NPC214644
0.8333	Intermediate Similarity	NPC11710
0.8318	Intermediate Similarity	NPC475060
0.8318	Intermediate Similarity	NPC477916
0.8318	Intermediate Similarity	NPC220229
0.8304	Intermediate Similarity	NPC239273
0.8302	Intermediate Similarity	NPC209502
0.8302	Intermediate Similarity	NPC204833
0.8286	Intermediate Similarity	NPC473424
0.8283	Intermediate Similarity	NPC326627
0.8283	Intermediate Similarity	NPC477943
0.8283	Intermediate Similarity	NPC310010
0.8273	Intermediate Similarity	NPC221144
0.8252	Intermediate Similarity	NPC472690
0.8252	Intermediate Similarity	NPC477268
0.8252	Intermediate Similarity	NPC472689
0.8252	Intermediate Similarity	NPC477267
0.8241	Intermediate Similarity	NPC217201
0.8235	Intermediate Similarity	NPC472932
0.8224	Intermediate Similarity	NPC149047
0.8224	Intermediate Similarity	NPC196528
0.8218	Intermediate Similarity	NPC233118
0.8205	Intermediate Similarity	NPC93368
0.819	Intermediate Similarity	NPC472924
0.8182	Intermediate Similarity	NPC470417
0.8182	Intermediate Similarity	NPC472928
0.8182	Intermediate Similarity	NPC207689
0.8165	Intermediate Similarity	NPC258543
0.8165	Intermediate Similarity	NPC241927
0.8158	Intermediate Similarity	NPC319570
0.8148	Intermediate Similarity	NPC185
0.8148	Intermediate Similarity	NPC472925
0.8137	Intermediate Similarity	NPC111015
0.8136	Intermediate Similarity	NPC152091
0.8131	Intermediate Similarity	NPC137657
0.8125	Intermediate Similarity	NPC247069
0.8125	Intermediate Similarity	NPC473898
0.812	Intermediate Similarity	NPC190846
0.812	Intermediate Similarity	NPC473255
0.812	Intermediate Similarity	NPC277191
0.8119	Intermediate Similarity	NPC19114
0.8113	Intermediate Similarity	NPC477915
0.8113	Intermediate Similarity	NPC473928
0.8108	Intermediate Similarity	NPC170487
0.8108	Intermediate Similarity	NPC207251
0.8108	Intermediate Similarity	NPC280782
0.8095	Intermediate Similarity	NPC154072
0.8095	Intermediate Similarity	NPC15390
0.8081	Intermediate Similarity	NPC90652
0.8077	Intermediate Similarity	NPC27105
0.8077	Intermediate Similarity	NPC273269
0.8058	Intermediate Similarity	NPC472824
0.8058	Intermediate Similarity	NPC263347
0.8058	Intermediate Similarity	NPC472485
0.8058	Intermediate Similarity	NPC200702
0.8056	Intermediate Similarity	NPC471332
0.8056	Intermediate Similarity	NPC471333
0.8056	Intermediate Similarity	NPC166607
0.8056	Intermediate Similarity	NPC257353
0.8053	Intermediate Similarity	NPC148458
0.8039	Intermediate Similarity	NPC472930
0.8039	Intermediate Similarity	NPC206810
0.8036	Intermediate Similarity	NPC962
0.8036	Intermediate Similarity	NPC317210
0.8036	Intermediate Similarity	NPC194100
0.8036	Intermediate Similarity	NPC250109
0.8036	Intermediate Similarity	NPC52634
0.802	Intermediate Similarity	NPC289213
0.802	Intermediate Similarity	NPC171441
0.8018	Intermediate Similarity	NPC214797
0.8018	Intermediate Similarity	NPC118860
0.8018	Intermediate Similarity	NPC231589
0.8017	Intermediate Similarity	NPC46570
0.8	Intermediate Similarity	NPC472933
0.8	Intermediate Similarity	NPC44181
0.8	Intermediate Similarity	NPC471330
0.8	Intermediate Similarity	NPC472687
0.8	Intermediate Similarity	NPC197386
0.8	Intermediate Similarity	NPC471331
0.8	Intermediate Similarity	NPC203388
0.8	Intermediate Similarity	NPC99657
0.7983	Intermediate Similarity	NPC470882
0.7983	Intermediate Similarity	NPC473265
0.7982	Intermediate Similarity	NPC471854
0.7982	Intermediate Similarity	NPC472934
0.7982	Intermediate Similarity	NPC44063
0.798	Intermediate Similarity	NPC327115
0.7965	Intermediate Similarity	NPC326542
0.7963	Intermediate Similarity	NPC160843
0.7963	Intermediate Similarity	NPC255309
0.7963	Intermediate Similarity	NPC13385
0.7963	Intermediate Similarity	NPC235889
0.7963	Intermediate Similarity	NPC477812
0.7963	Intermediate Similarity	NPC96268
0.7961	Intermediate Similarity	NPC298919
0.7961	Intermediate Similarity	NPC245972
0.7961	Intermediate Similarity	NPC196485
0.7961	Intermediate Similarity	NPC473172
0.7959	Intermediate Similarity	NPC473246
0.7949	Intermediate Similarity	NPC222688
0.7949	Intermediate Similarity	NPC107493
0.7946	Intermediate Similarity	NPC100267
0.7946	Intermediate Similarity	NPC71348
0.7946	Intermediate Similarity	NPC475524
0.7944	Intermediate Similarity	NPC204450
0.7944	Intermediate Similarity	NPC195290
0.7941	Intermediate Similarity	NPC168027
0.7941	Intermediate Similarity	NPC185936
0.7934	Intermediate Similarity	NPC213634
0.7931	Intermediate Similarity	NPC109973
0.7928	Intermediate Similarity	NPC76084
0.7925	Intermediate Similarity	NPC110149
0.7925	Intermediate Similarity	NPC83709
0.7925	Intermediate Similarity	NPC218383
0.7925	Intermediate Similarity	NPC316964
0.7921	Intermediate Similarity	NPC275740
0.7921	Intermediate Similarity	NPC86319
0.7921	Intermediate Similarity	NPC54689
0.7921	Intermediate Similarity	NPC186688
0.7921	Intermediate Similarity	NPC76879
0.7913	Intermediate Similarity	NPC257457
0.7913	Intermediate Similarity	NPC311554
0.7909	Intermediate Similarity	NPC9013
0.7905	Intermediate Similarity	NPC473161
0.7905	Intermediate Similarity	NPC190554
0.79	Intermediate Similarity	NPC99909
0.7895	Intermediate Similarity	NPC49492
0.7895	Intermediate Similarity	NPC266728
0.7895	Intermediate Similarity	NPC270958
0.789	Intermediate Similarity	NPC475494
0.789	Intermediate Similarity	NPC96377
0.789	Intermediate Similarity	NPC181265
0.789	Intermediate Similarity	NPC323834
0.7885	Intermediate Similarity	NPC473170
0.7879	Intermediate Similarity	NPC474218
0.7876	Intermediate Similarity	NPC202889
0.7876	Intermediate Similarity	NPC198539
0.7876	Intermediate Similarity	NPC472926
0.787	Intermediate Similarity	NPC249187
0.787	Intermediate Similarity	NPC474330
0.787	Intermediate Similarity	NPC236390
0.787	Intermediate Similarity	NPC247957
0.787	Intermediate Similarity	NPC474207
0.787	Intermediate Similarity	NPC159442
0.7864	Intermediate Similarity	NPC66429
0.7864	Intermediate Similarity	NPC243866
0.7864	Intermediate Similarity	NPC25750
0.7864	Intermediate Similarity	NPC250575
0.7864	Intermediate Similarity	NPC152897
0.7863	Intermediate Similarity	NPC471999
0.7863	Intermediate Similarity	NPC470921
0.7863	Intermediate Similarity	NPC472000
0.7857	Intermediate Similarity	NPC43775
0.7851	Intermediate Similarity	NPC470880
0.785	Intermediate Similarity	NPC163372
0.785	Intermediate Similarity	NPC470184
0.785	Intermediate Similarity	NPC475867
0.785	Intermediate Similarity	NPC270155

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 NPC58370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1784
0.2-0.3	4146
0.3-0.4	1989
0.4-0.5	587
0.5-0.6	191
0.6-0.7	127
0.7-0.8	123
0.8-0.85	22
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8774	High Similarity	NPD4634	Approved
0.8447	Intermediate Similarity	NPD4696	Approved
0.8447	Intermediate Similarity	NPD5285	Approved
0.8447	Intermediate Similarity	NPD5286	Approved
0.8431	Intermediate Similarity	NPD4755	Approved
0.8286	Intermediate Similarity	NPD4633	Approved
0.8286	Intermediate Similarity	NPD5226	Approved
0.8286	Intermediate Similarity	NPD5225	Approved
0.8286	Intermediate Similarity	NPD5224	Approved
0.8286	Intermediate Similarity	NPD5211	Phase 2
0.8283	Intermediate Similarity	NPD4753	Phase 2
0.8269	Intermediate Similarity	NPD4700	Approved
0.8246	Intermediate Similarity	NPD6319	Approved
0.8235	Intermediate Similarity	NPD5210	Approved
0.8235	Intermediate Similarity	NPD4629	Approved
0.8208	Intermediate Similarity	NPD5175	Approved
0.8208	Intermediate Similarity	NPD5174	Approved
0.819	Intermediate Similarity	NPD5223	Approved
0.8182	Intermediate Similarity	NPD6650	Approved
0.8182	Intermediate Similarity	NPD6649	Approved
0.8165	Intermediate Similarity	NPD6372	Approved
0.8165	Intermediate Similarity	NPD6373	Approved
0.8131	Intermediate Similarity	NPD5141	Approved
0.8108	Intermediate Similarity	NPD8297	Approved
0.8087	Intermediate Similarity	NPD6054	Approved
0.8073	Intermediate Similarity	NPD6899	Approved
0.8073	Intermediate Similarity	NPD4730	Approved
0.8073	Intermediate Similarity	NPD4729	Approved
0.8073	Intermediate Similarity	NPD6881	Approved
0.8056	Intermediate Similarity	NPD6675	Approved
0.8056	Intermediate Similarity	NPD6402	Approved
0.8056	Intermediate Similarity	NPD5739	Approved
0.8056	Intermediate Similarity	NPD4768	Approved
0.8056	Intermediate Similarity	NPD7128	Approved
0.8056	Intermediate Similarity	NPD4767	Approved
0.8036	Intermediate Similarity	NPD4632	Approved
0.7982	Intermediate Similarity	NPD5697	Approved
0.798	Intermediate Similarity	NPD5690	Phase 2
0.7949	Intermediate Similarity	NPD6370	Approved
0.7946	Intermediate Similarity	NPD6882	Approved
0.7931	Intermediate Similarity	NPD6059	Approved
0.7928	Intermediate Similarity	NPD5251	Approved
0.7928	Intermediate Similarity	NPD5247	Approved
0.7928	Intermediate Similarity	NPD6883	Approved
0.7928	Intermediate Similarity	NPD5248	Approved
0.7928	Intermediate Similarity	NPD5249	Phase 3
0.7928	Intermediate Similarity	NPD7290	Approved
0.7928	Intermediate Similarity	NPD5250	Approved
0.7928	Intermediate Similarity	NPD7102	Approved
0.7909	Intermediate Similarity	NPD5128	Approved
0.7909	Intermediate Similarity	NPD7320	Approved
0.7905	Intermediate Similarity	NPD6084	Phase 2
0.7905	Intermediate Similarity	NPD6083	Phase 2
0.7885	Intermediate Similarity	NPD5695	Phase 3
0.7879	Intermediate Similarity	NPD5329	Approved
0.787	Intermediate Similarity	NPD4754	Approved
0.7863	Intermediate Similarity	NPD6015	Approved
0.7863	Intermediate Similarity	NPD6016	Approved
0.7857	Intermediate Similarity	NPD8130	Phase 1
0.7857	Intermediate Similarity	NPD6617	Approved
0.7857	Intermediate Similarity	NPD6869	Approved
0.7857	Intermediate Similarity	NPD6847	Approved
0.7845	Intermediate Similarity	NPD4522	Approved
0.7838	Intermediate Similarity	NPD6013	Approved
0.7838	Intermediate Similarity	NPD6012	Approved
0.7838	Intermediate Similarity	NPD6014	Approved
0.7818	Intermediate Similarity	NPD5701	Approved
0.7815	Intermediate Similarity	NPD7492	Approved
0.781	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD5221	Approved
0.781	Intermediate Similarity	NPD5222	Approved
0.781	Intermediate Similarity	NPD4697	Phase 3
0.78	Intermediate Similarity	NPD5280	Approved
0.78	Intermediate Similarity	NPD4694	Approved
0.78	Intermediate Similarity	NPD5279	Phase 3
0.7797	Intermediate Similarity	NPD5988	Approved
0.7778	Intermediate Similarity	NPD4197	Approved
0.7778	Intermediate Similarity	NPD3665	Phase 1
0.7778	Intermediate Similarity	NPD3133	Approved
0.7778	Intermediate Similarity	NPD3666	Approved
0.7767	Intermediate Similarity	NPD6079	Approved
0.775	Intermediate Similarity	NPD6616	Approved
0.7748	Intermediate Similarity	NPD6011	Approved
0.7745	Intermediate Similarity	NPD5328	Approved
0.7736	Intermediate Similarity	NPD5173	Approved
0.7699	Intermediate Similarity	NPD5216	Approved
0.7699	Intermediate Similarity	NPD5215	Approved
0.7699	Intermediate Similarity	NPD5217	Approved
0.7692	Intermediate Similarity	NPD4202	Approved
0.7686	Intermediate Similarity	NPD7078	Approved
0.7672	Intermediate Similarity	NPD6009	Approved
0.7664	Intermediate Similarity	NPD5696	Approved
0.7658	Intermediate Similarity	NPD6412	Phase 2
0.7624	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD7736	Approved
0.7611	Intermediate Similarity	NPD5135	Approved
0.7611	Intermediate Similarity	NPD5169	Approved
0.7611	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD5284	Approved
0.7596	Intermediate Similarity	NPD5281	Approved
0.7576	Intermediate Similarity	NPD4221	Approved
0.7576	Intermediate Similarity	NPD4223	Phase 3
0.7544	Intermediate Similarity	NPD5127	Approved
0.7544	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD8293	Discontinued
0.75	Intermediate Similarity	NPD4788	Approved
0.7451	Intermediate Similarity	NPD3618	Phase 1
0.7438	Intermediate Similarity	NPD7604	Phase 2
0.7436	Intermediate Similarity	NPD6274	Approved
0.7426	Intermediate Similarity	NPD4786	Approved
0.7417	Intermediate Similarity	NPD5983	Phase 2
0.7395	Intermediate Similarity	NPD7101	Approved
0.7395	Intermediate Similarity	NPD7100	Approved
0.735	Intermediate Similarity	NPD5167	Approved
0.7339	Intermediate Similarity	NPD6033	Approved
0.7317	Intermediate Similarity	NPD6336	Discontinued
0.7311	Intermediate Similarity	NPD6335	Approved
0.7282	Intermediate Similarity	NPD4138	Approved
0.7282	Intermediate Similarity	NPD4689	Approved
0.7282	Intermediate Similarity	NPD4690	Approved
0.7282	Intermediate Similarity	NPD4688	Approved
0.7282	Intermediate Similarity	NPD4693	Phase 3
0.7282	Intermediate Similarity	NPD5205	Approved
0.7264	Intermediate Similarity	NPD6050	Approved
0.7257	Intermediate Similarity	NPD6008	Approved
0.7238	Intermediate Similarity	NPD6080	Approved
0.7238	Intermediate Similarity	NPD6673	Approved
0.7238	Intermediate Similarity	NPD6904	Approved
0.7228	Intermediate Similarity	NPD3667	Approved
0.7227	Intermediate Similarity	NPD7115	Discovery
0.7227	Intermediate Similarity	NPD6317	Approved
0.72	Intermediate Similarity	NPD4695	Discontinued
0.7196	Intermediate Similarity	NPD6399	Phase 3
0.7196	Intermediate Similarity	NPD5133	Approved
0.7179	Intermediate Similarity	NPD6053	Discontinued
0.7172	Intermediate Similarity	NPD3617	Approved
0.717	Intermediate Similarity	NPD5692	Phase 3
0.7167	Intermediate Similarity	NPD6313	Approved
0.7167	Intermediate Similarity	NPD6314	Approved
0.7154	Intermediate Similarity	NPD8328	Phase 3
0.7143	Intermediate Similarity	NPD7319	Approved
0.7143	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD5091	Approved
0.7131	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6908	Approved
0.7131	Intermediate Similarity	NPD6909	Approved
0.713	Intermediate Similarity	NPD5282	Discontinued
0.713	Intermediate Similarity	NPD5168	Approved
0.7115	Intermediate Similarity	NPD7146	Approved
0.7115	Intermediate Similarity	NPD6684	Approved
0.7115	Intermediate Similarity	NPD7521	Approved
0.7115	Intermediate Similarity	NPD7334	Approved
0.7115	Intermediate Similarity	NPD6409	Approved
0.7115	Intermediate Similarity	NPD5330	Approved
0.7103	Intermediate Similarity	NPD5694	Approved
0.71	Intermediate Similarity	NPD4195	Approved
0.7087	Intermediate Similarity	NPD5956	Approved
0.704	Intermediate Similarity	NPD7507	Approved
0.7009	Intermediate Similarity	NPD4096	Approved
0.6981	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6903	Approved
0.6961	Remote Similarity	NPD4692	Approved
0.6961	Remote Similarity	NPD4139	Approved
0.6952	Remote Similarity	NPD6098	Approved
0.6944	Remote Similarity	NPD5693	Phase 1
0.6909	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6371	Approved
0.686	Remote Similarity	NPD6868	Approved
0.6852	Remote Similarity	NPD5207	Approved
0.6838	Remote Similarity	NPD6686	Approved
0.6838	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4518	Approved
0.6789	Remote Similarity	NPD6411	Approved
0.6789	Remote Similarity	NPD7515	Phase 2
0.6769	Remote Similarity	NPD7260	Phase 2
0.6762	Remote Similarity	NPD3668	Phase 3
0.6759	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5654	Approved
0.6731	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7638	Approved
0.672	Remote Similarity	NPD7503	Approved
0.6699	Remote Similarity	NPD5368	Approved
0.6699	Remote Similarity	NPD7525	Registered
0.6698	Remote Similarity	NPD5363	Approved
0.6697	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7902	Approved
0.6637	Remote Similarity	NPD5959	Approved
0.6635	Remote Similarity	NPD5369	Approved
0.6634	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6614	Approved
0.6606	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6101	Approved
0.66	Remote Similarity	NPD5733	Approved
0.6593	Remote Similarity	NPD6334	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