NPASS Compound

Structure

NPC475751 OpenBabel07101718332D 32 35 0 0 1 0 0 0 0 0999 V2000 -5.0605 -3.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4570 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -2.4135 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 -3.4133 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 -2.9680 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -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 -4.7004 -5.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3914 -4.1270 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.1261 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 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 -0.8660 -1.5000 0.0000 C 0 0 1 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 2 0 0 0 0 0 0 0 0 0 -5.6786 -5.2859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 0.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 20 1 0 0 0 0 9 25 1 0 0 0 0 10 24 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 15 2 1 6 0 0 0 15 16 1 0 0 0 0 16 24 1 1 0 0 0 17 22 1 0 0 0 0 17 28 1 1 0 0 0 18 23 1 0 0 0 0 18 29 1 1 0 0 0 19 21 1 0 0 0 0 19 30 1 6 0 0 0 20 25 1 1 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 25 1 1 0 0 0 22 31 1 1 0 0 0 23 24 1 1 0 0 0 23 26 1 0 0 0 0 24 3 1 1 0 0 0 25 4 1 1 0 0 0 26 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.31
Volume:	474.131
LogP:	2.021
LogD:	2.516
LogS:	-3.438
# Rotatable Bonds:	4
TPSA:	121.38
# H-Bond Aceptor:	6
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	5.311
Fsp3:	0.923
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.227
MDCK Permeability:	6.898515130160376e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.904
20% Bioavailability (F20%):	0.686
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225
Plasma Protein Binding (PPB):	81.8254623413086%
Volume Distribution (VD):	0.594
Pgp-substrate:	2.835792064666748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.841
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.738
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.154
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	1.198
Half-life (T1/2):	0.319

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.346
Maximum Recommended Daily Dose:	0.164
Skin Sensitization:	0.323
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC475751

Natural Product ID:	NPC475751
*Common Name:**	(3S,4R,5S,6S,8S,9R,10S,13R,14S,15R,17R)-17-((2R,E)-6-Hydroxy-5-Methylhex-3-En-2-Yl)-10,13-Dimethylhexadecahydro-1H-Cyclopenta[A]Phenanthrene-3,4,6,8,15-Pentaol
IUPAC Name:	(3S,4R,5S,6S,8S,9R,10S,13R,14S,15R,17R)-17-[(E,2R)-6-hydroxy-5-methylhex-3-en-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,4,6,8,15-pentol
Synonyms:
Standard InCHIKey:	SLZPIGPCASURLO-SCOCZYPQSA-N
Standard InCHI:	InChI=1S/C26H44O6/c1-14(13-27)5-6-15(2)16-11-18(29)23-24(16,3)10-8-20-25(4)9-7-17(28)22(31)21(25)19(30)12-26(20,23)32/h5-6,14-23,27-32H,7-13H2,1-4H3/b6-5+/t14?,15-,16-,17+,18-,19+,20-,21+,22+,23-,24-,25-,26+/m1/s1
SMILES:	CC(CO)C=CC(C)C1CC(C2C1(CCC3C2(CC(C4C3(CCC(C4O)O)C)O)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513972
PubChem CID:	21589766
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003027] 3-hydroxysteroids [CHEMONTID:0003233] 3-beta-hydroxysteroids

*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
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444692]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662097]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104487]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497935]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[527142]
NPT574	Cell Line	XF498	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[527142]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[527142]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[527142]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[527142]

☑ 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 NPC475751 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	198
0.1-0.2	1607
0.2-0.3	5809
0.3-0.4	14650
0.4-0.5	8874
0.5-0.6	5041
0.6-0.7	4702
0.7-0.8	1617
0.8-0.85	135
0.85-0.9	47
0.9-0.95	10
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473956
0.9881	High Similarity	NPC109744
0.9762	High Similarity	NPC475664
0.9643	High Similarity	NPC474657
0.9643	High Similarity	NPC186145
0.9524	High Similarity	NPC6605
0.9294	High Similarity	NPC201273
0.9294	High Similarity	NPC121981
0.9286	High Similarity	NPC475798
0.9286	High Similarity	NPC127606
0.9195	High Similarity	NPC105495
0.9167	High Similarity	NPC193870
0.9167	High Similarity	NPC141941
0.9121	High Similarity	NPC477226
0.9059	High Similarity	NPC255882
0.9011	High Similarity	NPC471903
0.8989	High Similarity	NPC275671
0.8989	High Similarity	NPC41554
0.8989	High Similarity	NPC97404
0.8941	High Similarity	NPC477818
0.8941	High Similarity	NPC207013
0.8941	High Similarity	NPC85095
0.8941	High Similarity	NPC232023
0.8941	High Similarity	NPC110778
0.8941	High Similarity	NPC216420
0.8941	High Similarity	NPC211135
0.8876	High Similarity	NPC291484
0.8876	High Similarity	NPC204188
0.8876	High Similarity	NPC3345
0.8876	High Similarity	NPC80561
0.8876	High Similarity	NPC329596
0.8876	High Similarity	NPC11216
0.8851	High Similarity	NPC24277
0.8851	High Similarity	NPC71520
0.8851	High Similarity	NPC139724
0.8851	High Similarity	NPC269058
0.8837	High Similarity	NPC124172
0.8764	High Similarity	NPC470361
0.871	High Similarity	NPC474994
0.871	High Similarity	NPC476040
0.871	High Similarity	NPC316604
0.871	High Similarity	NPC476021
0.8652	High Similarity	NPC474668
0.8652	High Similarity	NPC133588
0.8636	High Similarity	NPC94462
0.8636	High Similarity	NPC299068
0.8621	High Similarity	NPC209802
0.8605	High Similarity	NPC30166
0.8605	High Similarity	NPC470614
0.8605	High Similarity	NPC1272
0.8602	High Similarity	NPC288970
0.8588	High Similarity	NPC236237
0.8588	High Similarity	NPC322313
0.8588	High Similarity	NPC78545
0.8588	High Similarity	NPC102253
0.8588	High Similarity	NPC13554
0.8588	High Similarity	NPC71535
0.8587	High Similarity	NPC127718
0.8587	High Similarity	NPC65402
0.8523	High Similarity	NPC470360
0.8506	High Similarity	NPC113978
0.8495	Intermediate Similarity	NPC8774
0.8488	Intermediate Similarity	NPC470383
0.8488	Intermediate Similarity	NPC474531
0.8478	Intermediate Similarity	NPC310013
0.8478	Intermediate Similarity	NPC98193
0.8471	Intermediate Similarity	NPC80530
0.8471	Intermediate Similarity	NPC273410
0.8452	Intermediate Similarity	NPC477227
0.8452	Intermediate Similarity	NPC105208
0.8452	Intermediate Similarity	NPC192046
0.8452	Intermediate Similarity	NPC128951
0.8452	Intermediate Similarity	NPC302578
0.8444	Intermediate Similarity	NPC4574
0.8444	Intermediate Similarity	NPC212596
0.8444	Intermediate Similarity	NPC67872
0.8444	Intermediate Similarity	NPC475605
0.8444	Intermediate Similarity	NPC470542
0.8427	Intermediate Similarity	NPC152808
0.8427	Intermediate Similarity	NPC293287
0.8427	Intermediate Similarity	NPC261266
0.8427	Intermediate Similarity	NPC237344
0.8427	Intermediate Similarity	NPC6391
0.8409	Intermediate Similarity	NPC474493
0.8409	Intermediate Similarity	NPC256567
0.8404	Intermediate Similarity	NPC98457
0.8404	Intermediate Similarity	NPC227583
0.8404	Intermediate Similarity	NPC12103
0.8391	Intermediate Similarity	NPC7988
0.8372	Intermediate Similarity	NPC236112
0.8372	Intermediate Similarity	NPC287749
0.8372	Intermediate Similarity	NPC26117
0.837	Intermediate Similarity	NPC210268
0.8353	Intermediate Similarity	NPC477819
0.8353	Intermediate Similarity	NPC167037
0.8353	Intermediate Similarity	NPC148977
0.8353	Intermediate Similarity	NPC244385
0.8353	Intermediate Similarity	NPC138621
0.8353	Intermediate Similarity	NPC18857
0.8353	Intermediate Similarity	NPC477817
0.8353	Intermediate Similarity	NPC67657
0.8353	Intermediate Similarity	NPC285761
0.8353	Intermediate Similarity	NPC6978
0.8353	Intermediate Similarity	NPC31828
0.8352	Intermediate Similarity	NPC101886
0.8333	Intermediate Similarity	NPC304083
0.8333	Intermediate Similarity	NPC470620
0.8333	Intermediate Similarity	NPC208358
0.8333	Intermediate Similarity	NPC163597
0.8333	Intermediate Similarity	NPC477600
0.8316	Intermediate Similarity	NPC475032
0.8316	Intermediate Similarity	NPC476893
0.8316	Intermediate Similarity	NPC475033
0.8315	Intermediate Similarity	NPC318390
0.8261	Intermediate Similarity	NPC470390
0.8261	Intermediate Similarity	NPC107189
0.8261	Intermediate Similarity	NPC192437
0.8261	Intermediate Similarity	NPC270511
0.8261	Intermediate Similarity	NPC14380
0.8261	Intermediate Similarity	NPC245410
0.8256	Intermediate Similarity	NPC1319
0.8256	Intermediate Similarity	NPC472463
0.8256	Intermediate Similarity	NPC328714
0.8247	Intermediate Similarity	NPC155974
0.8242	Intermediate Similarity	NPC2158
0.8242	Intermediate Similarity	NPC473436
0.8235	Intermediate Similarity	NPC185915
0.8229	Intermediate Similarity	NPC476895
0.8214	Intermediate Similarity	NPC158208
0.8214	Intermediate Similarity	NPC103822
0.8214	Intermediate Similarity	NPC317242
0.8214	Intermediate Similarity	NPC196136
0.8214	Intermediate Similarity	NPC243027
0.8211	Intermediate Similarity	NPC210717
0.8211	Intermediate Similarity	NPC103165
0.8202	Intermediate Similarity	NPC185568
0.8202	Intermediate Similarity	NPC238992
0.8202	Intermediate Similarity	NPC205845
0.8202	Intermediate Similarity	NPC469878
0.8191	Intermediate Similarity	NPC477605
0.8182	Intermediate Similarity	NPC248886
0.8182	Intermediate Similarity	NPC296701
0.8182	Intermediate Similarity	NPC218616
0.8182	Intermediate Similarity	NPC312774
0.8172	Intermediate Similarity	NPC219516
0.8161	Intermediate Similarity	NPC475679
0.8161	Intermediate Similarity	NPC47149
0.8161	Intermediate Similarity	NPC22403
0.8152	Intermediate Similarity	NPC138974
0.8152	Intermediate Similarity	NPC187785
0.8152	Intermediate Similarity	NPC74258
0.8152	Intermediate Similarity	NPC259875
0.814	Intermediate Similarity	NPC477522
0.814	Intermediate Similarity	NPC87604
0.8132	Intermediate Similarity	NPC475313
0.8132	Intermediate Similarity	NPC271967
0.8125	Intermediate Similarity	NPC261807
0.8118	Intermediate Similarity	NPC91573
0.8118	Intermediate Similarity	NPC237460
0.8111	Intermediate Similarity	NPC474189
0.8111	Intermediate Similarity	NPC474349
0.81	Intermediate Similarity	NPC474015
0.8095	Intermediate Similarity	NPC228994
0.8095	Intermediate Similarity	NPC10476
0.8095	Intermediate Similarity	NPC304499
0.8095	Intermediate Similarity	NPC192501
0.809	Intermediate Similarity	NPC317458
0.809	Intermediate Similarity	NPC470558
0.809	Intermediate Similarity	NPC159168
0.809	Intermediate Similarity	NPC320548
0.809	Intermediate Similarity	NPC82623
0.809	Intermediate Similarity	NPC134481
0.809	Intermediate Similarity	NPC474634
0.809	Intermediate Similarity	NPC253402
0.809	Intermediate Similarity	NPC470929
0.8081	Intermediate Similarity	NPC191892
0.8081	Intermediate Similarity	NPC475701
0.8068	Intermediate Similarity	NPC471270
0.8068	Intermediate Similarity	NPC157655
0.8065	Intermediate Similarity	NPC295668
0.8061	Intermediate Similarity	NPC476896
0.8061	Intermediate Similarity	NPC474022
0.8046	Intermediate Similarity	NPC116119
0.8046	Intermediate Similarity	NPC24504
0.8046	Intermediate Similarity	NPC476316
0.8046	Intermediate Similarity	NPC80297
0.8046	Intermediate Similarity	NPC475727
0.8046	Intermediate Similarity	NPC287452
0.8046	Intermediate Similarity	NPC472742
0.8043	Intermediate Similarity	NPC280556
0.8041	Intermediate Similarity	NPC309493
0.8041	Intermediate Similarity	NPC300179
0.8041	Intermediate Similarity	NPC102426
0.8023	Intermediate Similarity	NPC318495
0.8023	Intermediate Similarity	NPC471798
0.8023	Intermediate Similarity	NPC477924
0.8023	Intermediate Similarity	NPC130136
0.8023	Intermediate Similarity	NPC198968
0.8023	Intermediate Similarity	NPC155986
0.8022	Intermediate Similarity	NPC477604

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 NPC475751 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1805
0.2-0.3	4383
0.3-0.4	1930
0.4-0.5	414
0.5-0.6	178
0.6-0.7	181
0.7-0.8	75
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8588	High Similarity	NPD7525	Registered
0.7935	Intermediate Similarity	NPD7524	Approved
0.7907	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6932	Approved
0.7802	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6942	Approved
0.7791	Intermediate Similarity	NPD7339	Approved
0.7753	Intermediate Similarity	NPD6931	Approved
0.7753	Intermediate Similarity	NPD6930	Phase 2
0.7742	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6933	Approved
0.7692	Intermediate Similarity	NPD6695	Phase 3
0.7674	Intermediate Similarity	NPD4785	Approved
0.7674	Intermediate Similarity	NPD4784	Approved
0.764	Intermediate Similarity	NPD6929	Approved
0.7619	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7514	Phase 3
0.7528	Intermediate Similarity	NPD7145	Approved
0.7471	Intermediate Similarity	NPD6926	Approved
0.7471	Intermediate Similarity	NPD6924	Approved
0.7453	Intermediate Similarity	NPD4634	Approved
0.7444	Intermediate Similarity	NPD6683	Phase 2
0.7444	Intermediate Similarity	NPD7645	Phase 2
0.7442	Intermediate Similarity	NPD4243	Approved
0.7426	Intermediate Similarity	NPD5285	Approved
0.7426	Intermediate Similarity	NPD4696	Approved
0.7426	Intermediate Similarity	NPD5286	Approved
0.7416	Intermediate Similarity	NPD5776	Phase 2
0.7416	Intermediate Similarity	NPD6925	Approved
0.74	Intermediate Similarity	NPD4755	Approved
0.7387	Intermediate Similarity	NPD7516	Approved
0.7368	Intermediate Similarity	NPD7750	Discontinued
0.7363	Intermediate Similarity	NPD7332	Phase 2
0.7363	Intermediate Similarity	NPD4748	Discontinued
0.7347	Intermediate Similarity	NPD4202	Approved
0.734	Intermediate Similarity	NPD6893	Approved
0.7297	Intermediate Similarity	NPD7328	Approved
0.7297	Intermediate Similarity	NPD7327	Approved
0.7283	Intermediate Similarity	NPD6902	Approved
0.7282	Intermediate Similarity	NPD5225	Approved
0.7282	Intermediate Similarity	NPD5211	Phase 2
0.7282	Intermediate Similarity	NPD4633	Approved
0.7282	Intermediate Similarity	NPD5224	Approved
0.7282	Intermediate Similarity	NPD5226	Approved
0.7255	Intermediate Similarity	NPD4700	Approved
0.7241	Intermediate Similarity	NPD7150	Approved
0.7241	Intermediate Similarity	NPD7152	Approved
0.7241	Intermediate Similarity	NPD7151	Approved
0.7234	Intermediate Similarity	NPD4786	Approved
0.7212	Intermediate Similarity	NPD5175	Approved
0.7212	Intermediate Similarity	NPD5174	Approved
0.7184	Intermediate Similarity	NPD5223	Approved
0.7174	Intermediate Similarity	NPD7509	Discontinued
0.7157	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD5141	Approved
0.7126	Intermediate Similarity	NPD7144	Approved
0.7126	Intermediate Similarity	NPD7143	Approved
0.7105	Intermediate Similarity	NPD8380	Approved
0.7105	Intermediate Similarity	NPD8335	Approved
0.7105	Intermediate Similarity	NPD8379	Approved
0.7105	Intermediate Similarity	NPD8378	Approved
0.7105	Intermediate Similarity	NPD8296	Approved
0.7105	Intermediate Similarity	NPD8033	Approved
0.7103	Intermediate Similarity	NPD6881	Approved
0.7103	Intermediate Similarity	NPD6899	Approved
0.7097	Intermediate Similarity	NPD6898	Phase 1
0.7091	Intermediate Similarity	NPD4632	Approved
0.7087	Intermediate Similarity	NPD7639	Approved
0.7087	Intermediate Similarity	NPD7640	Approved
0.7075	Intermediate Similarity	NPD6675	Approved
0.7075	Intermediate Similarity	NPD6402	Approved
0.7075	Intermediate Similarity	NPD7128	Approved
0.7075	Intermediate Similarity	NPD5739	Approved
0.7071	Intermediate Similarity	NPD7087	Discontinued
0.7071	Intermediate Similarity	NPD6079	Approved
0.7065	Intermediate Similarity	NPD4195	Approved
0.7041	Intermediate Similarity	NPD5328	Approved
0.7041	Intermediate Similarity	NPD4753	Phase 2
0.7021	Intermediate Similarity	NPD3667	Approved
0.7019	Intermediate Similarity	NPD4159	Approved
0.7018	Intermediate Similarity	NPD8294	Approved
0.7018	Intermediate Similarity	NPD8377	Approved
0.7011	Intermediate Similarity	NPD6923	Approved
0.7011	Intermediate Similarity	NPD6922	Approved
0.7009	Intermediate Similarity	NPD5697	Approved
0.7	Intermediate Similarity	NPD8297	Approved
0.7	Intermediate Similarity	NPD5275	Approved
0.7	Intermediate Similarity	NPD4190	Phase 3
0.6972	Remote Similarity	NPD6883	Approved
0.6972	Remote Similarity	NPD7102	Approved
0.6972	Remote Similarity	NPD7290	Approved
0.6944	Remote Similarity	NPD7320	Approved
0.6944	Remote Similarity	NPD4730	Approved
0.6944	Remote Similarity	NPD4729	Approved
0.6932	Remote Similarity	NPD4787	Phase 1
0.6916	Remote Similarity	NPD4767	Approved
0.6916	Remote Similarity	NPD4768	Approved
0.6909	Remote Similarity	NPD6649	Approved
0.6909	Remote Similarity	NPD6847	Approved
0.6909	Remote Similarity	NPD8130	Phase 1
0.6909	Remote Similarity	NPD6650	Approved
0.6909	Remote Similarity	NPD6617	Approved
0.6909	Remote Similarity	NPD6869	Approved
0.6907	Remote Similarity	NPD3618	Phase 1
0.6887	Remote Similarity	NPD4754	Approved
0.6881	Remote Similarity	NPD6372	Approved
0.6881	Remote Similarity	NPD6373	Approved
0.6881	Remote Similarity	NPD6012	Approved
0.6881	Remote Similarity	NPD6014	Approved
0.6881	Remote Similarity	NPD6013	Approved
0.6875	Remote Similarity	NPD3666	Approved
0.6875	Remote Similarity	NPD3133	Approved
0.6875	Remote Similarity	NPD3665	Phase 1
0.687	Remote Similarity	NPD6319	Approved
0.687	Remote Similarity	NPD6054	Approved
0.6863	Remote Similarity	NPD4629	Approved
0.6863	Remote Similarity	NPD5210	Approved
0.6852	Remote Similarity	NPD6412	Phase 2
0.6852	Remote Similarity	NPD5701	Approved
0.6847	Remote Similarity	NPD6882	Approved
0.6832	Remote Similarity	NPD6399	Phase 3
0.6818	Remote Similarity	NPD5251	Approved
0.6818	Remote Similarity	NPD5247	Approved
0.6818	Remote Similarity	NPD5248	Approved
0.6818	Remote Similarity	NPD5249	Phase 3
0.6818	Remote Similarity	NPD5250	Approved
0.681	Remote Similarity	NPD7503	Approved
0.6804	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5221	Approved
0.6796	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5222	Approved
0.6789	Remote Similarity	NPD6011	Approved
0.6789	Remote Similarity	NPD5128	Approved
0.6774	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4788	Approved
0.6757	Remote Similarity	NPD5217	Approved
0.6757	Remote Similarity	NPD5216	Approved
0.6757	Remote Similarity	NPD5215	Approved
0.6754	Remote Similarity	NPD6009	Approved
0.6752	Remote Similarity	NPD6370	Approved
0.6733	Remote Similarity	NPD7637	Suspended
0.6731	Remote Similarity	NPD5173	Approved
0.6731	Remote Similarity	NPD6083	Phase 2
0.6731	Remote Similarity	NPD6084	Phase 2
0.6724	Remote Similarity	NPD6059	Approved
0.6723	Remote Similarity	NPD7507	Approved
0.6694	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD7492	Approved
0.6635	Remote Similarity	NPD4697	Phase 3
0.6634	Remote Similarity	NPD7136	Phase 2
0.6633	Remote Similarity	NPD5329	Approved
0.6632	Remote Similarity	NPD6928	Phase 2
0.6612	Remote Similarity	NPD7736	Approved
0.661	Remote Similarity	NPD5988	Approved
0.6609	Remote Similarity	NPD7115	Discovery
0.6607	Remote Similarity	NPD5127	Approved
0.6607	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6008	Approved
0.6596	Remote Similarity	NPD6118	Approved
0.6596	Remote Similarity	NPD6114	Approved
0.6596	Remote Similarity	NPD6697	Approved
0.6596	Remote Similarity	NPD6115	Approved
0.6583	Remote Similarity	NPD6616	Approved
0.6569	Remote Similarity	NPD8034	Phase 2
0.6569	Remote Similarity	NPD8035	Phase 2
0.6569	Remote Similarity	NPD7515	Phase 2
0.6555	Remote Similarity	NPD7604	Phase 2
0.6542	Remote Similarity	NPD5344	Discontinued
0.6535	Remote Similarity	NPD6051	Approved
0.6531	Remote Similarity	NPD3668	Phase 3
0.6531	Remote Similarity	NPD4197	Approved
0.6529	Remote Similarity	NPD7078	Approved
0.6525	Remote Similarity	NPD5983	Phase 2
0.6505	Remote Similarity	NPD8171	Discontinued
0.6496	Remote Similarity	NPD4522	Approved
0.6496	Remote Similarity	NPD7101	Approved
0.6496	Remote Similarity	NPD7100	Approved
0.6489	Remote Similarity	NPD6116	Phase 1
0.6486	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7632	Discontinued
0.6458	Remote Similarity	NPD4820	Approved
0.6458	Remote Similarity	NPD4821	Approved
0.6458	Remote Similarity	NPD4819	Approved
0.6458	Remote Similarity	NPD4822	Approved
0.6452	Remote Similarity	NPD8264	Approved
0.6446	Remote Similarity	NPD6336	Discontinued
0.6435	Remote Similarity	NPD5167	Approved
0.6429	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6335	Approved
0.6408	Remote Similarity	NPD5284	Approved
0.6408	Remote Similarity	NPD5281	Approved
0.64	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4689	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