NPASS Compound

Structure

NPC170221 OpenBabel07101718272D 37 40 0 0 1 0 0 0 0 0999 V2000 -2.1072 2.5367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8117 4.1190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0303 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8982 1.1351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3904 1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3686 0.9965 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 3.4641 0.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6958 3.2177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9162 3.1245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8298 2.7177 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0377 1.7396 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 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 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4390 2.5486 0.0000 C 0 0 1 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 -0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0322 1.6351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 2.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4171 2.7565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0322 0.6351 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 1 18 2 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 10 11 2 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 27 1 0 0 0 0 14 31 1 0 0 0 0 15 30 1 0 0 0 0 16 21 1 0 0 0 0 16 26 1 0 0 0 0 17 23 1 0 0 0 0 17 25 1 0 0 0 0 19 28 2 0 0 0 0 20 33 2 0 0 0 0 20 37 1 0 0 0 0 21 18 1 1 0 0 0 21 22 1 0 0 0 0 22 32 1 6 0 0 0 23 28 1 0 0 0 0 23 34 2 0 0 0 0 24 29 1 0 0 0 0 24 30 1 6 0 0 0 25 30 1 1 0 0 0 25 31 1 0 0 0 0 26 32 1 1 0 0 0 26 35 1 0 0 0 0 27 29 1 0 0 0 0 27 37 1 6 0 0 0 28 31 1 0 0 0 0 30 7 1 6 0 0 0 31 8 1 1 0 0 0 32 9 1 6 0 0 0 32 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.35
Volume:	558.571
LogP:	4.892
LogD:	4.337
LogS:	-4.959
# Rotatable Bonds:	5
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	5.394
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.715
MDCK Permeability:	2.359305290156044e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.382
30% Bioavailability (F30%):	0.771

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.971
Plasma Protein Binding (PPB):	68.84229278564453%
Volume Distribution (VD):	1.095
Pgp-substrate:	27.360326766967773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.106
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.261
CYP3A4-substrate:	0.526

ADMET: Excretion

Clearance (CL):	3.774
Half-life (T1/2):	0.072

ADMET: Toxicity

hERG Blockers:	0.154
Human Hepatotoxicity (H-HT):	0.342
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.46
Carcinogencity:	0.173
Eye Corrosion:	0.012
Eye Irritation:	0.018
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC170221

Natural Product ID:	NPC170221
*Common Name:**	Rhabdastin D
IUPAC Name:	[(3Z,3aS,5aR,7S,9aR,9bS)-3-[(E)-4-[(1S,2R,3S,5R)-2,3-dihydroxy-2-methyl-5-prop-1-en-2-ylcyclopentyl]but-3-en-2-ylidene]-3a,6,6,9a-tetramethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalen-7-yl] acetate
Synonyms:	Rhabdastin D
Standard InCHIKey:	JCHRBDNNUVYAGR-CMMKBFFWSA-N
Standard InCHI:	InChI=1S/C32H48O5/c1-18(2)21-16-26(35)32(9,36)22(21)11-10-19(3)28-23(34)17-25-30(7)15-13-27(37-20(4)33)29(5,6)24(30)12-14-31(25,28)8/h10-11,21-22,24-27,35-36H,1,12-17H2,2-9H3/b11-10+,28-19+/t21-,22-,24-,25-,26-,27-,30-,31-,32+/m0/s1
SMILES:	C=C(C)[C@@H]1C[C@@H]([C@@](C)([C@H]1/C=C/C(=C/1C(=O)C[C@H]2[C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3CC[C@]12C)OC(=O)C)/C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224727
PubChem CID:	46938850
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858759]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499318]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562838]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17524651]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20627740]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20718449]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	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	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	21000.0	nM	PMID[533941]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	18.0	%	PMID[533941]

☑ 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 NPC170221 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	1000
0.2-0.3	4044
0.3-0.4	9442
0.4-0.5	12422
0.5-0.6	6415
0.6-0.7	6914
0.7-0.8	2139
0.8-0.85	104
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC10064
0.9901	High Similarity	NPC6206
0.9314	High Similarity	NPC469874
0.8679	High Similarity	NPC473284
0.8641	High Similarity	NPC266955
0.8558	High Similarity	NPC115899
0.8519	High Similarity	NPC475065
0.8476	Intermediate Similarity	NPC32577
0.8476	Intermediate Similarity	NPC114540
0.8476	Intermediate Similarity	NPC155332
0.8476	Intermediate Similarity	NPC22388
0.8447	Intermediate Similarity	NPC108078
0.844	Intermediate Similarity	NPC197428
0.844	Intermediate Similarity	NPC5284
0.8431	Intermediate Similarity	NPC279974
0.8426	Intermediate Similarity	NPC472825
0.8426	Intermediate Similarity	NPC473482
0.8426	Intermediate Similarity	NPC475418
0.8426	Intermediate Similarity	NPC318363
0.8396	Intermediate Similarity	NPC475050
0.8365	Intermediate Similarity	NPC477854
0.835	Intermediate Similarity	NPC471153
0.8333	Intermediate Similarity	NPC329048
0.8333	Intermediate Similarity	NPC330011
0.8318	Intermediate Similarity	NPC477812
0.8288	Intermediate Similarity	NPC71348
0.8288	Intermediate Similarity	NPC475970
0.8288	Intermediate Similarity	NPC280782
0.8273	Intermediate Similarity	NPC179642
0.8269	Intermediate Similarity	NPC474785
0.8269	Intermediate Similarity	NPC474938
0.8257	Intermediate Similarity	NPC472218
0.8257	Intermediate Similarity	NPC472219
0.8257	Intermediate Similarity	NPC472217
0.8252	Intermediate Similarity	NPC88310
0.8241	Intermediate Similarity	NPC231530
0.8241	Intermediate Similarity	NPC278628
0.823	Intermediate Similarity	NPC49492
0.823	Intermediate Similarity	NPC266728
0.8224	Intermediate Similarity	NPC72151
0.8218	Intermediate Similarity	NPC475965
0.8218	Intermediate Similarity	NPC474842
0.8214	Intermediate Similarity	NPC250109
0.8214	Intermediate Similarity	NPC178981
0.8214	Intermediate Similarity	NPC962
0.819	Intermediate Similarity	NPC114274
0.819	Intermediate Similarity	NPC477813
0.819	Intermediate Similarity	NPC470921
0.819	Intermediate Similarity	NPC108368
0.819	Intermediate Similarity	NPC57079
0.819	Intermediate Similarity	NPC119036
0.8182	Intermediate Similarity	NPC173905
0.8182	Intermediate Similarity	NPC5475
0.8182	Intermediate Similarity	NPC284828
0.8182	Intermediate Similarity	NPC472216
0.8173	Intermediate Similarity	NPC477853
0.8173	Intermediate Similarity	NPC250757
0.8173	Intermediate Similarity	NPC301534
0.8158	Intermediate Similarity	NPC471854
0.8155	Intermediate Similarity	NPC473431
0.8155	Intermediate Similarity	NPC473280
0.8155	Intermediate Similarity	NPC111015
0.8155	Intermediate Similarity	NPC473435
0.8155	Intermediate Similarity	NPC471078
0.8148	Intermediate Similarity	NPC471293
0.8148	Intermediate Similarity	NPC255309
0.8136	Intermediate Similarity	NPC473255
0.8131	Intermediate Similarity	NPC473163
0.8131	Intermediate Similarity	NPC320447
0.8131	Intermediate Similarity	NPC477054
0.8125	Intermediate Similarity	NPC152117
0.8125	Intermediate Similarity	NPC234042
0.8125	Intermediate Similarity	NPC470063
0.8113	Intermediate Similarity	NPC35751
0.8113	Intermediate Similarity	NPC167974
0.8108	Intermediate Similarity	NPC16270
0.81	Intermediate Similarity	NPC141292
0.8095	Intermediate Similarity	NPC110937
0.8091	Intermediate Similarity	NPC258323
0.8091	Intermediate Similarity	NPC94529
0.8087	Intermediate Similarity	NPC311554
0.8087	Intermediate Similarity	NPC257457
0.8077	Intermediate Similarity	NPC472824
0.8077	Intermediate Similarity	NPC469599
0.8073	Intermediate Similarity	NPC96377
0.8073	Intermediate Similarity	NPC149047
0.8073	Intermediate Similarity	NPC186668
0.807	Intermediate Similarity	NPC270958
0.807	Intermediate Similarity	NPC196931
0.8056	Intermediate Similarity	NPC473283
0.8056	Intermediate Similarity	NPC222153
0.8056	Intermediate Similarity	NPC329345
0.8056	Intermediate Similarity	NPC140723
0.8056	Intermediate Similarity	NPC475526
0.8053	Intermediate Similarity	NPC255017
0.8053	Intermediate Similarity	NPC194100
0.8053	Intermediate Similarity	NPC52634
0.8051	Intermediate Similarity	NPC473979
0.8039	Intermediate Similarity	NPC471896
0.8037	Intermediate Similarity	NPC477053
0.8037	Intermediate Similarity	NPC99411
0.8037	Intermediate Similarity	NPC282524
0.8037	Intermediate Similarity	NPC477051
0.8037	Intermediate Similarity	NPC477052
0.8036	Intermediate Similarity	NPC43775
0.802	Intermediate Similarity	NPC310752
0.802	Intermediate Similarity	NPC292491
0.8018	Intermediate Similarity	NPC474901
0.8018	Intermediate Similarity	NPC475941
0.8018	Intermediate Similarity	NPC41405
0.8018	Intermediate Similarity	NPC241927
0.8018	Intermediate Similarity	NPC258543
0.8017	Intermediate Similarity	NPC305260
0.8017	Intermediate Similarity	NPC475041
0.8017	Intermediate Similarity	NPC473203
0.8017	Intermediate Similarity	NPC270850
0.8	Intermediate Similarity	NPC473265
0.8	Intermediate Similarity	NPC220229
0.8	Intermediate Similarity	NPC173272
0.8	Intermediate Similarity	NPC475060
0.8	Intermediate Similarity	NPC220974
0.8	Intermediate Similarity	NPC59530
0.8	Intermediate Similarity	NPC44063
0.7982	Intermediate Similarity	NPC209502
0.7982	Intermediate Similarity	NPC29705
0.7982	Intermediate Similarity	NPC477580
0.7982	Intermediate Similarity	NPC204833
0.7981	Intermediate Similarity	NPC245972
0.7981	Intermediate Similarity	NPC474690
0.7981	Intermediate Similarity	NPC196485
0.7981	Intermediate Similarity	NPC299100
0.7966	Intermediate Similarity	NPC222688
0.7965	Intermediate Similarity	NPC207251
0.7963	Intermediate Similarity	NPC473928
0.7961	Intermediate Similarity	NPC26888
0.7961	Intermediate Similarity	NPC189520
0.7949	Intermediate Similarity	NPC79579
0.7949	Intermediate Similarity	NPC41123
0.7949	Intermediate Similarity	NPC109973
0.7949	Intermediate Similarity	NPC145074
0.7949	Intermediate Similarity	NPC114939
0.7946	Intermediate Similarity	NPC101450
0.7946	Intermediate Similarity	NPC239097
0.7946	Intermediate Similarity	NPC475134
0.7946	Intermediate Similarity	NPC76084
0.7946	Intermediate Similarity	NPC475563
0.7944	Intermediate Similarity	NPC154072
0.7944	Intermediate Similarity	NPC83709
0.7944	Intermediate Similarity	NPC208358
0.7944	Intermediate Similarity	NPC316964
0.7941	Intermediate Similarity	NPC476733
0.7941	Intermediate Similarity	NPC269267
0.7941	Intermediate Similarity	NPC215029
0.7941	Intermediate Similarity	NPC32830
0.7941	Intermediate Similarity	NPC128496
0.7934	Intermediate Similarity	NPC473888
0.7931	Intermediate Similarity	NPC118638
0.7931	Intermediate Similarity	NPC473828
0.7931	Intermediate Similarity	NPC473617
0.7931	Intermediate Similarity	NPC146786
0.7928	Intermediate Similarity	NPC217201
0.7928	Intermediate Similarity	NPC19412
0.7925	Intermediate Similarity	NPC475033
0.7925	Intermediate Similarity	NPC320306
0.7925	Intermediate Similarity	NPC469432
0.7925	Intermediate Similarity	NPC475032
0.7925	Intermediate Similarity	NPC99726
0.7917	Intermediate Similarity	NPC15095
0.7913	Intermediate Similarity	NPC148458
0.7913	Intermediate Similarity	NPC190286
0.7913	Intermediate Similarity	NPC298278
0.7909	Intermediate Similarity	NPC49958
0.7909	Intermediate Similarity	NPC196528
0.7909	Intermediate Similarity	NPC319077
0.7909	Intermediate Similarity	NPC296945
0.7909	Intermediate Similarity	NPC60315
0.7909	Intermediate Similarity	NPC302607
0.7909	Intermediate Similarity	NPC323834
0.7909	Intermediate Similarity	NPC266570
0.7909	Intermediate Similarity	NPC475414
0.7909	Intermediate Similarity	NPC50692
0.7909	Intermediate Similarity	NPC257353
0.7909	Intermediate Similarity	NPC214264
0.7909	Intermediate Similarity	NPC48733
0.7909	Intermediate Similarity	NPC181265
0.7909	Intermediate Similarity	NPC97202
0.7909	Intermediate Similarity	NPC470309
0.7909	Intermediate Similarity	NPC260268
0.7909	Intermediate Similarity	NPC171137
0.7909	Intermediate Similarity	NPC472655
0.7909	Intermediate Similarity	NPC150531
0.7909	Intermediate Similarity	NPC152695
0.7909	Intermediate Similarity	NPC476027
0.7909	Intermediate Similarity	NPC202167
0.7909	Intermediate Similarity	NPC85829
0.7909	Intermediate Similarity	NPC173172
0.7905	Intermediate Similarity	NPC37787
0.7905	Intermediate Similarity	NPC180557
0.7905	Intermediate Similarity	NPC469329
0.7905	Intermediate Similarity	NPC222845

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 NPC170221 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1220
0.2-0.3	3730
0.3-0.4	2720
0.4-0.5	746
0.5-0.6	217
0.6-0.7	183
0.7-0.8	149
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8257	Intermediate Similarity	NPD7320	Approved
0.8125	Intermediate Similarity	NPD8297	Approved
0.8091	Intermediate Similarity	NPD6899	Approved
0.8091	Intermediate Similarity	NPD6881	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
0.8053	Intermediate Similarity	NPD4632	Approved
0.8036	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD5697	Approved
0.7949	Intermediate Similarity	NPD6319	Approved
0.7946	Intermediate Similarity	NPD7102	Approved
0.7946	Intermediate Similarity	NPD7290	Approved
0.7946	Intermediate Similarity	NPD6883	Approved
0.7928	Intermediate Similarity	NPD6011	Approved
0.7925	Intermediate Similarity	NPD6084	Phase 2
0.7925	Intermediate Similarity	NPD6083	Phase 2
0.7909	Intermediate Similarity	NPD6008	Approved
0.7876	Intermediate Similarity	NPD6617	Approved
0.7876	Intermediate Similarity	NPD6650	Approved
0.7876	Intermediate Similarity	NPD6869	Approved
0.7876	Intermediate Similarity	NPD6649	Approved
0.7876	Intermediate Similarity	NPD6847	Approved
0.7857	Intermediate Similarity	NPD6372	Approved
0.7857	Intermediate Similarity	NPD6013	Approved
0.7857	Intermediate Similarity	NPD6014	Approved
0.7857	Intermediate Similarity	NPD6012	Approved
0.7857	Intermediate Similarity	NPD6373	Approved
0.7851	Intermediate Similarity	NPD7078	Approved
0.785	Intermediate Similarity	NPD7638	Approved
0.7843	Intermediate Similarity	NPD6903	Approved
0.7838	Intermediate Similarity	NPD5701	Approved
0.7833	Intermediate Similarity	NPD7492	Approved
0.7807	Intermediate Similarity	NPD6882	Approved
0.7797	Intermediate Similarity	NPD6054	Approved
0.7788	Intermediate Similarity	NPD4634	Approved
0.7787	Intermediate Similarity	NPD7736	Approved
0.7778	Intermediate Similarity	NPD7640	Approved
0.7778	Intermediate Similarity	NPD7639	Approved
0.7769	Intermediate Similarity	NPD6616	Approved
0.7736	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6399	Phase 3
0.7714	Intermediate Similarity	NPD4202	Approved
0.7705	Intermediate Similarity	NPD8293	Discontinued
0.7692	Intermediate Similarity	NPD7115	Discovery
0.7692	Intermediate Similarity	NPD6009	Approved
0.7667	Intermediate Similarity	NPD6370	Approved
0.7647	Intermediate Similarity	NPD6684	Approved
0.7647	Intermediate Similarity	NPD5330	Approved
0.7647	Intermediate Similarity	NPD6059	Approved
0.7647	Intermediate Similarity	NPD7521	Approved
0.7647	Intermediate Similarity	NPD7334	Approved
0.7647	Intermediate Similarity	NPD7146	Approved
0.7647	Intermediate Similarity	NPD6409	Approved
0.7642	Intermediate Similarity	NPD7748	Approved
0.7619	Intermediate Similarity	NPD5284	Approved
0.7619	Intermediate Similarity	NPD6079	Approved
0.7619	Intermediate Similarity	NPD5281	Approved
0.7615	Intermediate Similarity	NPD5285	Approved
0.7615	Intermediate Similarity	NPD4696	Approved
0.7615	Intermediate Similarity	NPD5286	Approved
0.7603	Intermediate Similarity	NPD7604	Phase 2
0.7596	Intermediate Similarity	NPD5328	Approved
0.7593	Intermediate Similarity	NPD4755	Approved
0.7583	Intermediate Similarity	NPD6015	Approved
0.7583	Intermediate Similarity	NPD5983	Phase 2
0.7583	Intermediate Similarity	NPD6016	Approved
0.757	Intermediate Similarity	NPD5695	Phase 3
0.7545	Intermediate Similarity	NPD5223	Approved
0.7524	Intermediate Similarity	NPD5207	Approved
0.7523	Intermediate Similarity	NPD5696	Approved
0.7522	Intermediate Similarity	NPD6412	Phase 2
0.7521	Intermediate Similarity	NPD5988	Approved
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD7507	Approved
0.748	Intermediate Similarity	NPD6336	Discontinued
0.7479	Intermediate Similarity	NPD6335	Approved
0.7477	Intermediate Similarity	NPD5224	Approved
0.7477	Intermediate Similarity	NPD5226	Approved
0.7477	Intermediate Similarity	NPD4633	Approved
0.7477	Intermediate Similarity	NPD5211	Phase 2
0.7477	Intermediate Similarity	NPD5225	Approved
0.7476	Intermediate Similarity	NPD3618	Phase 1
0.7455	Intermediate Similarity	NPD4700	Approved
0.7453	Intermediate Similarity	NPD6050	Approved
0.7453	Intermediate Similarity	NPD7515	Phase 2
0.7453	Intermediate Similarity	NPD5694	Approved
0.7451	Intermediate Similarity	NPD3665	Phase 1
0.7451	Intermediate Similarity	NPD3133	Approved
0.7451	Intermediate Similarity	NPD3666	Approved
0.7451	Intermediate Similarity	NPD4786	Approved
0.7431	Intermediate Similarity	NPD7902	Approved
0.7429	Intermediate Similarity	NPD4753	Phase 2
0.7429	Intermediate Similarity	NPD6904	Approved
0.7429	Intermediate Similarity	NPD6673	Approved
0.7429	Intermediate Similarity	NPD6080	Approved
0.7417	Intermediate Similarity	NPD7101	Approved
0.7417	Intermediate Similarity	NPD7100	Approved
0.7411	Intermediate Similarity	NPD5175	Approved
0.7411	Intermediate Similarity	NPD5174	Approved
0.7395	Intermediate Similarity	NPD6317	Approved
0.7358	Intermediate Similarity	NPD5692	Phase 3
0.7345	Intermediate Similarity	NPD5141	Approved
0.7339	Intermediate Similarity	NPD5221	Approved
0.7339	Intermediate Similarity	NPD5222	Approved
0.7339	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5737	Approved
0.7333	Intermediate Similarity	NPD6314	Approved
0.7333	Intermediate Similarity	NPD6313	Approved
0.7333	Intermediate Similarity	NPD6672	Approved
0.7315	Intermediate Similarity	NPD6001	Approved
0.7311	Intermediate Similarity	NPD6274	Approved
0.7302	Intermediate Similarity	NPD7319	Approved
0.7295	Intermediate Similarity	NPD8033	Approved
0.7295	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD8034	Phase 2
0.729	Intermediate Similarity	NPD7637	Suspended
0.729	Intermediate Similarity	NPD8035	Phase 2
0.7273	Intermediate Similarity	NPD5173	Approved
0.7257	Intermediate Similarity	NPD4754	Approved
0.7255	Intermediate Similarity	NPD4223	Phase 3
0.7255	Intermediate Similarity	NPD3667	Approved
0.7255	Intermediate Similarity	NPD4221	Approved
0.7248	Intermediate Similarity	NPD5210	Approved
0.7248	Intermediate Similarity	NPD4629	Approved
0.7222	Intermediate Similarity	NPD6033	Approved
0.7213	Intermediate Similarity	NPD8377	Approved
0.7213	Intermediate Similarity	NPD8294	Approved
0.7212	Intermediate Similarity	NPD5329	Approved
0.7212	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6053	Discontinued
0.719	Intermediate Similarity	NPD7328	Approved
0.719	Intermediate Similarity	NPD7327	Approved
0.7182	Intermediate Similarity	NPD4697	Phase 3
0.7177	Intermediate Similarity	NPD6067	Discontinued
0.717	Intermediate Similarity	NPD5208	Approved
0.7168	Intermediate Similarity	NPD7632	Discontinued
0.7167	Intermediate Similarity	NPD6868	Approved
0.7156	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7900	Approved
0.7155	Intermediate Similarity	NPD4729	Approved
0.7155	Intermediate Similarity	NPD4730	Approved
0.7154	Intermediate Similarity	NPD6909	Approved
0.7154	Intermediate Similarity	NPD8380	Approved
0.7154	Intermediate Similarity	NPD7503	Approved
0.7154	Intermediate Similarity	NPD8379	Approved
0.7154	Intermediate Similarity	NPD8378	Approved
0.7154	Intermediate Similarity	NPD8296	Approved
0.7154	Intermediate Similarity	NPD8335	Approved
0.7154	Intermediate Similarity	NPD6908	Approved
0.7143	Intermediate Similarity	NPD5280	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD4694	Approved
0.7143	Intermediate Similarity	NPD6098	Approved
0.7131	Intermediate Similarity	NPD7516	Approved
0.713	Intermediate Similarity	NPD4767	Approved
0.713	Intermediate Similarity	NPD4768	Approved
0.713	Intermediate Similarity	NPD5693	Phase 1
0.7115	Intermediate Similarity	NPD4197	Approved
0.7075	Intermediate Similarity	NPD7524	Approved
0.7054	Intermediate Similarity	NPD4225	Approved
0.7034	Intermediate Similarity	NPD5247	Approved
0.7034	Intermediate Similarity	NPD5135	Approved
0.7034	Intermediate Similarity	NPD5248	Approved
0.7034	Intermediate Similarity	NPD5169	Approved
0.7034	Intermediate Similarity	NPD5250	Approved
0.7034	Intermediate Similarity	NPD5249	Phase 3
0.7034	Intermediate Similarity	NPD5251	Approved
0.7034	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5362	Discontinued
0.7019	Intermediate Similarity	NPD4788	Approved
0.7019	Intermediate Similarity	NPD6695	Phase 3
0.7009	Intermediate Similarity	NPD5128	Approved
0.7	Intermediate Similarity	NPD6933	Approved
0.699	Remote Similarity	NPD5369	Approved
0.6981	Remote Similarity	NPD5205	Approved
0.6981	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4689	Approved
0.6981	Remote Similarity	NPD4693	Phase 3
0.6981	Remote Similarity	NPD4138	Approved
0.6981	Remote Similarity	NPD4690	Approved
0.6981	Remote Similarity	NPD5690	Phase 2
0.6981	Remote Similarity	NPD4688	Approved
0.6975	Remote Similarity	NPD5217	Approved
0.6975	Remote Similarity	NPD5216	Approved
0.6975	Remote Similarity	NPD5127	Approved
0.6975	Remote Similarity	NPD5215	Approved
0.6972	Remote Similarity	NPD6411	Approved
0.6952	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5654	Approved
0.6916	Remote Similarity	NPD3573	Approved
0.6916	Remote Similarity	NPD7750	Discontinued
0.6909	Remote Similarity	NPD5779	Approved
0.6909	Remote Similarity	NPD5778	Approved
0.6893	Remote Similarity	NPD7525	Registered
0.6881	Remote Similarity	NPD5785	Approved
0.6864	Remote Similarity	NPD6686	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