NPASS Compound

Structure

NPC6206 OpenBabel07101719252D 38 41 0 0 1 0 0 0 0 0999 V2000 -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 -2.3285 3.9335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3230 4.0380 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 -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 -4.0377 1.7396 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8298 2.7177 0.0000 C 0 0 2 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 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 -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 -2.9162 3.1245 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 -2.1072 2.5367 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 1 0 0 0 0 2 19 1 0 0 0 0 3 28 1 0 0 0 0 4 28 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 18 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 26 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 25 1 0 0 0 0 17 22 1 0 0 0 0 17 24 1 0 0 0 0 18 27 2 0 0 0 0 19 33 2 0 0 0 0 19 38 1 0 0 0 0 20 21 1 0 0 0 0 20 32 1 6 0 0 0 21 29 1 1 0 0 0 22 27 1 0 0 0 0 22 34 2 0 0 0 0 23 28 1 0 0 0 0 23 30 1 6 0 0 0 24 30 1 1 0 0 0 24 31 1 0 0 0 0 25 32 1 6 0 0 0 25 35 1 0 0 0 0 26 28 1 0 0 0 0 26 38 1 6 0 0 0 27 31 1 0 0 0 0 29 36 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 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.36
Volume:	569.998
LogP:	4.591
LogD:	3.833
LogS:	-4.549
# Rotatable Bonds:	5
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.343
Synthetic Accessibility Score:	5.215
Fsp3:	0.812
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:	2.2189622541191056e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.226
30% Bioavailability (F30%):	0.331

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.159
Plasma Protein Binding (PPB):	87.59467315673828%
Volume Distribution (VD):	0.988
Pgp-substrate:	8.162586212158203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.735
CYP2C9-inhibitor:	0.137
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.593
CYP3A4-substrate:	0.536

ADMET: Excretion

Clearance (CL):	2.656
Half-life (T1/2):	0.148

ADMET: Toxicity

hERG Blockers:	0.22
Human Hepatotoxicity (H-HT):	0.456
Drug-inuced Liver Injury (DILI):	0.142
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.783
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.717
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC6206

Natural Product ID:	NPC6206
*Common Name:**	Rhabdastin G
IUPAC Name:	[(3Z,3aS,5aR,7S,9aR,9bS)-3-[(E)-4-[(1S,2R,3R,5R)-2,3-dihydroxy-5-(2-hydroxypropan-2-yl)-2-methylcyclopentyl]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 G
Standard InCHIKey:	XYIKEKVGSQWPLG-BNHQCWCPSA-N
Standard InCHI:	InChI=1S/C32H50O6/c1-18(10-11-20-21(29(5,6)36)16-25(35)32(20,9)37)27-22(34)17-24-30(7)15-13-26(38-19(2)33)28(3,4)23(30)12-14-31(24,27)8/h10-11,20-21,23-26,35-37H,12-17H2,1-9H3/b11-10+,27-18+/t20-,21+,23-,24-,25+,26-,30-,31-,32+/m0/s1
SMILES:	CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@]1([C@H]2CC(=O)/C/1=C(C=C[C@H]1[C@@H](C[C@H]([C@]1(C)O)O)C(O)(C)C)/C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224729
PubChem CID:	46938943
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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	44000.0	nM	PMID[481696]

☑ 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 NPC6206 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	212
0.1-0.2	1030
0.2-0.3	4043
0.3-0.4	9122
0.4-0.5	12632
0.5-0.6	6228
0.6-0.7	7006
0.7-0.8	2314
0.8-0.85	103
0.85-0.9	3
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9901	High Similarity	NPC10064
0.9901	High Similarity	NPC170221
0.9223	High Similarity	NPC469874
0.8598	High Similarity	NPC473284
0.8571	High Similarity	NPC22388
0.8558	High Similarity	NPC266955
0.8532	High Similarity	NPC197428
0.8476	Intermediate Similarity	NPC115899
0.844	Intermediate Similarity	NPC475065
0.8411	Intermediate Similarity	NPC477812
0.8396	Intermediate Similarity	NPC114540
0.8396	Intermediate Similarity	NPC32577
0.8396	Intermediate Similarity	NPC155332
0.8378	Intermediate Similarity	NPC71348
0.8365	Intermediate Similarity	NPC108078
0.8364	Intermediate Similarity	NPC5284
0.835	Intermediate Similarity	NPC279974
0.8349	Intermediate Similarity	NPC472217
0.8349	Intermediate Similarity	NPC472825
0.8349	Intermediate Similarity	NPC472218
0.8349	Intermediate Similarity	NPC475418
0.8349	Intermediate Similarity	NPC473482
0.8349	Intermediate Similarity	NPC318363
0.8349	Intermediate Similarity	NPC472219
0.8333	Intermediate Similarity	NPC278628
0.8333	Intermediate Similarity	NPC231530
0.8319	Intermediate Similarity	NPC266728
0.8319	Intermediate Similarity	NPC49492
0.8318	Intermediate Similarity	NPC475050
0.8304	Intermediate Similarity	NPC962
0.8304	Intermediate Similarity	NPC178981
0.8304	Intermediate Similarity	NPC250109
0.8286	Intermediate Similarity	NPC477854
0.8286	Intermediate Similarity	NPC477813
0.8273	Intermediate Similarity	NPC5475
0.8273	Intermediate Similarity	NPC472216
0.8273	Intermediate Similarity	NPC173905
0.8273	Intermediate Similarity	NPC284828
0.8269	Intermediate Similarity	NPC471153
0.8257	Intermediate Similarity	NPC329048
0.8257	Intermediate Similarity	NPC330011
0.8252	Intermediate Similarity	NPC111015
0.822	Intermediate Similarity	NPC473255
0.8214	Intermediate Similarity	NPC152117
0.8214	Intermediate Similarity	NPC475970
0.8214	Intermediate Similarity	NPC234042
0.8214	Intermediate Similarity	NPC280782
0.8208	Intermediate Similarity	NPC167974
0.8198	Intermediate Similarity	NPC179642
0.819	Intermediate Similarity	NPC474938
0.819	Intermediate Similarity	NPC474785
0.8182	Intermediate Similarity	NPC94529
0.8182	Intermediate Similarity	NPC258323
0.8173	Intermediate Similarity	NPC88310
0.8158	Intermediate Similarity	NPC270958
0.8148	Intermediate Similarity	NPC72151
0.8148	Intermediate Similarity	NPC140723
0.8142	Intermediate Similarity	NPC52634
0.8142	Intermediate Similarity	NPC194100
0.8142	Intermediate Similarity	NPC255017
0.8137	Intermediate Similarity	NPC475965
0.8137	Intermediate Similarity	NPC474842
0.8136	Intermediate Similarity	NPC473979
0.812	Intermediate Similarity	NPC470921
0.8113	Intermediate Similarity	NPC57079
0.8113	Intermediate Similarity	NPC108368
0.8113	Intermediate Similarity	NPC119036
0.8113	Intermediate Similarity	NPC114274
0.8108	Intermediate Similarity	NPC41405
0.8108	Intermediate Similarity	NPC258543
0.8108	Intermediate Similarity	NPC241927
0.8103	Intermediate Similarity	NPC305260
0.8103	Intermediate Similarity	NPC475041
0.8103	Intermediate Similarity	NPC270850
0.8103	Intermediate Similarity	NPC473203
0.8095	Intermediate Similarity	NPC477853
0.8095	Intermediate Similarity	NPC301534
0.8095	Intermediate Similarity	NPC250757
0.8091	Intermediate Similarity	NPC44063
0.8091	Intermediate Similarity	NPC475060
0.8091	Intermediate Similarity	NPC220229
0.8091	Intermediate Similarity	NPC59530
0.8087	Intermediate Similarity	NPC471854
0.8083	Intermediate Similarity	NPC473265
0.8077	Intermediate Similarity	NPC473280
0.8077	Intermediate Similarity	NPC471078
0.8077	Intermediate Similarity	NPC473431
0.8077	Intermediate Similarity	NPC473435
0.8073	Intermediate Similarity	NPC255309
0.8073	Intermediate Similarity	NPC471293
0.8073	Intermediate Similarity	NPC29705
0.807	Intermediate Similarity	NPC477580
0.8056	Intermediate Similarity	NPC477054
0.8056	Intermediate Similarity	NPC473163
0.8056	Intermediate Similarity	NPC320447
0.8056	Intermediate Similarity	NPC473928
0.8053	Intermediate Similarity	NPC207251
0.8053	Intermediate Similarity	NPC470063
0.8051	Intermediate Similarity	NPC222688
0.8037	Intermediate Similarity	NPC35751
0.8037	Intermediate Similarity	NPC208358
0.8037	Intermediate Similarity	NPC154072
0.8036	Intermediate Similarity	NPC475563
0.8036	Intermediate Similarity	NPC101450
0.8036	Intermediate Similarity	NPC475134
0.8036	Intermediate Similarity	NPC16270
0.8034	Intermediate Similarity	NPC41123
0.8034	Intermediate Similarity	NPC145074
0.8034	Intermediate Similarity	NPC79579
0.8034	Intermediate Similarity	NPC109973
0.8034	Intermediate Similarity	NPC114939
0.802	Intermediate Similarity	NPC141292
0.8019	Intermediate Similarity	NPC475033
0.8019	Intermediate Similarity	NPC475032
0.8019	Intermediate Similarity	NPC469432
0.8019	Intermediate Similarity	NPC110937
0.8018	Intermediate Similarity	NPC217201
0.8017	Intermediate Similarity	NPC257457
0.8017	Intermediate Similarity	NPC473888
0.8017	Intermediate Similarity	NPC118638
0.8017	Intermediate Similarity	NPC473828
0.8017	Intermediate Similarity	NPC311554
0.8017	Intermediate Similarity	NPC473617
0.8	Intermediate Similarity	NPC296945
0.8	Intermediate Similarity	NPC302607
0.8	Intermediate Similarity	NPC319077
0.8	Intermediate Similarity	NPC214264
0.8	Intermediate Similarity	NPC45324
0.8	Intermediate Similarity	NPC476027
0.8	Intermediate Similarity	NPC190286
0.8	Intermediate Similarity	NPC475414
0.8	Intermediate Similarity	NPC50692
0.8	Intermediate Similarity	NPC171137
0.8	Intermediate Similarity	NPC202167
0.8	Intermediate Similarity	NPC69548
0.8	Intermediate Similarity	NPC149047
0.8	Intermediate Similarity	NPC97202
0.8	Intermediate Similarity	NPC150531
0.8	Intermediate Similarity	NPC60315
0.8	Intermediate Similarity	NPC96377
0.8	Intermediate Similarity	NPC162001
0.8	Intermediate Similarity	NPC173172
0.8	Intermediate Similarity	NPC470309
0.8	Intermediate Similarity	NPC85829
0.8	Intermediate Similarity	NPC323834
0.8	Intermediate Similarity	NPC184848
0.8	Intermediate Similarity	NPC152695
0.8	Intermediate Similarity	NPC196931
0.8	Intermediate Similarity	NPC49958
0.8	Intermediate Similarity	NPC298278
0.8	Intermediate Similarity	NPC186668
0.8	Intermediate Similarity	NPC222845
0.8	Intermediate Similarity	NPC48733
0.8	Intermediate Similarity	NPC472824
0.8	Intermediate Similarity	NPC469599
0.8	Intermediate Similarity	NPC181265
0.8	Intermediate Similarity	NPC260268
0.7983	Intermediate Similarity	NPC6193
0.7982	Intermediate Similarity	NPC475526
0.7982	Intermediate Similarity	NPC260665
0.7982	Intermediate Similarity	NPC202889
0.7982	Intermediate Similarity	NPC477944
0.7982	Intermediate Similarity	NPC329345
0.7982	Intermediate Similarity	NPC222153
0.7982	Intermediate Similarity	NPC472821
0.7982	Intermediate Similarity	NPC473283
0.7981	Intermediate Similarity	NPC470376
0.7981	Intermediate Similarity	NPC470375
0.7965	Intermediate Similarity	NPC475668
0.7965	Intermediate Similarity	NPC473921
0.7965	Intermediate Similarity	NPC231589
0.7965	Intermediate Similarity	NPC43775
0.7965	Intermediate Similarity	NPC214797
0.7965	Intermediate Similarity	NPC475480
0.7965	Intermediate Similarity	NPC118860
0.7963	Intermediate Similarity	NPC99411
0.7963	Intermediate Similarity	NPC477051
0.7963	Intermediate Similarity	NPC155974
0.7963	Intermediate Similarity	NPC282524
0.7963	Intermediate Similarity	NPC477053
0.7963	Intermediate Similarity	NPC477052
0.7961	Intermediate Similarity	NPC471896
0.7951	Intermediate Similarity	NPC470880
0.7946	Intermediate Similarity	NPC218853
0.7946	Intermediate Similarity	NPC474901
0.7946	Intermediate Similarity	NPC2766
0.7946	Intermediate Similarity	NPC11710
0.7946	Intermediate Similarity	NPC475941
0.7944	Intermediate Similarity	NPC186810
0.7941	Intermediate Similarity	NPC310752
0.7941	Intermediate Similarity	NPC292491
0.7934	Intermediate Similarity	NPC473253
0.7934	Intermediate Similarity	NPC470882
0.7928	Intermediate Similarity	NPC220974
0.7928	Intermediate Similarity	NPC475176
0.7928	Intermediate Similarity	NPC83744
0.7928	Intermediate Similarity	NPC67321
0.7928	Intermediate Similarity	NPC187435
0.7925	Intermediate Similarity	NPC173272
0.7925	Intermediate Similarity	NPC253115

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 NPC6206 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1236
0.2-0.3	3730
0.3-0.4	2695
0.4-0.5	752
0.5-0.6	224
0.6-0.7	176
0.7-0.8	137
0.8-0.85	18
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8349	Intermediate Similarity	NPD7320	Approved
0.8214	Intermediate Similarity	NPD8297	Approved
0.8182	Intermediate Similarity	NPD6899	Approved
0.8182	Intermediate Similarity	NPD6881	Approved
0.8165	Intermediate Similarity	NPD7128	Approved
0.8165	Intermediate Similarity	NPD6675	Approved
0.8165	Intermediate Similarity	NPD6402	Approved
0.8165	Intermediate Similarity	NPD5739	Approved
0.8142	Intermediate Similarity	NPD4632	Approved
0.8125	Intermediate Similarity	NPD8130	Phase 1
0.8091	Intermediate Similarity	NPD5697	Approved
0.8036	Intermediate Similarity	NPD7102	Approved
0.8036	Intermediate Similarity	NPD7290	Approved
0.8036	Intermediate Similarity	NPD6883	Approved
0.8034	Intermediate Similarity	NPD6319	Approved
0.8018	Intermediate Similarity	NPD6011	Approved
0.8	Intermediate Similarity	NPD6008	Approved
0.7965	Intermediate Similarity	NPD6617	Approved
0.7965	Intermediate Similarity	NPD6869	Approved
0.7965	Intermediate Similarity	NPD6649	Approved
0.7965	Intermediate Similarity	NPD6847	Approved
0.7965	Intermediate Similarity	NPD6650	Approved
0.7946	Intermediate Similarity	NPD6012	Approved
0.7946	Intermediate Similarity	NPD6373	Approved
0.7946	Intermediate Similarity	NPD6372	Approved
0.7946	Intermediate Similarity	NPD6014	Approved
0.7946	Intermediate Similarity	NPD6013	Approved
0.7934	Intermediate Similarity	NPD7078	Approved
0.7928	Intermediate Similarity	NPD5701	Approved
0.7917	Intermediate Similarity	NPD7492	Approved
0.7895	Intermediate Similarity	NPD6882	Approved
0.7881	Intermediate Similarity	NPD6054	Approved
0.7876	Intermediate Similarity	NPD4634	Approved
0.7869	Intermediate Similarity	NPD7736	Approved
0.7851	Intermediate Similarity	NPD6616	Approved
0.785	Intermediate Similarity	NPD6084	Phase 2
0.785	Intermediate Similarity	NPD6083	Phase 2
0.781	Intermediate Similarity	NPD4202	Approved
0.781	Intermediate Similarity	NPD6399	Phase 3
0.7807	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD8293	Discontinued
0.7778	Intermediate Similarity	NPD7638	Approved
0.7778	Intermediate Similarity	NPD6009	Approved
0.7767	Intermediate Similarity	NPD6903	Approved
0.775	Intermediate Similarity	NPD6370	Approved
0.7731	Intermediate Similarity	NPD6059	Approved
0.7714	Intermediate Similarity	NPD5281	Approved
0.7714	Intermediate Similarity	NPD5284	Approved
0.7706	Intermediate Similarity	NPD5285	Approved
0.7706	Intermediate Similarity	NPD7640	Approved
0.7706	Intermediate Similarity	NPD4696	Approved
0.7706	Intermediate Similarity	NPD7639	Approved
0.7706	Intermediate Similarity	NPD5286	Approved
0.7686	Intermediate Similarity	NPD7604	Phase 2
0.7685	Intermediate Similarity	NPD4755	Approved
0.7667	Intermediate Similarity	NPD6015	Approved
0.7667	Intermediate Similarity	NPD6016	Approved
0.7667	Intermediate Similarity	NPD5983	Phase 2
0.7664	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5223	Approved
0.7627	Intermediate Similarity	NPD7115	Discovery
0.7611	Intermediate Similarity	NPD6412	Phase 2
0.7603	Intermediate Similarity	NPD5988	Approved
0.7573	Intermediate Similarity	NPD7146	Approved
0.7573	Intermediate Similarity	NPD7334	Approved
0.7573	Intermediate Similarity	NPD5330	Approved
0.7573	Intermediate Similarity	NPD6409	Approved
0.7573	Intermediate Similarity	NPD7521	Approved
0.7573	Intermediate Similarity	NPD6684	Approved
0.757	Intermediate Similarity	NPD7748	Approved
0.7568	Intermediate Similarity	NPD5224	Approved
0.7568	Intermediate Similarity	NPD5211	Phase 2
0.7568	Intermediate Similarity	NPD5225	Approved
0.7568	Intermediate Similarity	NPD4633	Approved
0.7568	Intermediate Similarity	NPD5226	Approved
0.7563	Intermediate Similarity	NPD6335	Approved
0.7561	Intermediate Similarity	NPD6336	Discontinued
0.7561	Intermediate Similarity	NPD7507	Approved
0.7547	Intermediate Similarity	NPD6079	Approved
0.7545	Intermediate Similarity	NPD4700	Approved
0.7524	Intermediate Similarity	NPD5328	Approved
0.7523	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD7101	Approved
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD5695	Phase 3
0.75	Intermediate Similarity	NPD5174	Approved
0.7479	Intermediate Similarity	NPD6317	Approved
0.7455	Intermediate Similarity	NPD5696	Approved
0.7453	Intermediate Similarity	NPD5207	Approved
0.7434	Intermediate Similarity	NPD5141	Approved
0.7429	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6313	Approved
0.7417	Intermediate Similarity	NPD6314	Approved
0.7404	Intermediate Similarity	NPD3618	Phase 1
0.7395	Intermediate Similarity	NPD6274	Approved
0.7383	Intermediate Similarity	NPD5694	Approved
0.7383	Intermediate Similarity	NPD7515	Phase 2
0.7383	Intermediate Similarity	NPD6050	Approved
0.7383	Intermediate Similarity	NPD8035	Phase 2
0.7383	Intermediate Similarity	NPD8034	Phase 2
0.7381	Intermediate Similarity	NPD7319	Approved
0.7379	Intermediate Similarity	NPD3133	Approved
0.7379	Intermediate Similarity	NPD4786	Approved
0.7379	Intermediate Similarity	NPD3665	Phase 1
0.7379	Intermediate Similarity	NPD3666	Approved
0.7377	Intermediate Similarity	NPD8033	Approved
0.7377	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6904	Approved
0.7358	Intermediate Similarity	NPD6080	Approved
0.7358	Intermediate Similarity	NPD6673	Approved
0.7358	Intermediate Similarity	NPD4753	Phase 2
0.7345	Intermediate Similarity	NPD4754	Approved
0.7302	Intermediate Similarity	NPD6033	Approved
0.7295	Intermediate Similarity	NPD8294	Approved
0.7295	Intermediate Similarity	NPD8377	Approved
0.729	Intermediate Similarity	NPD5692	Phase 3
0.7288	Intermediate Similarity	NPD6053	Discontinued
0.7273	Intermediate Similarity	NPD7328	Approved
0.7273	Intermediate Similarity	NPD5221	Approved
0.7273	Intermediate Similarity	NPD5222	Approved
0.7273	Intermediate Similarity	NPD7327	Approved
0.7273	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5737	Approved
0.7264	Intermediate Similarity	NPD6672	Approved
0.7258	Intermediate Similarity	NPD6067	Discontinued
0.7248	Intermediate Similarity	NPD6001	Approved
0.7248	Intermediate Similarity	NPD7900	Approved
0.7248	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4730	Approved
0.7241	Intermediate Similarity	NPD4729	Approved
0.7236	Intermediate Similarity	NPD6908	Approved
0.7236	Intermediate Similarity	NPD8335	Approved
0.7236	Intermediate Similarity	NPD6909	Approved
0.7236	Intermediate Similarity	NPD8378	Approved
0.7236	Intermediate Similarity	NPD8380	Approved
0.7236	Intermediate Similarity	NPD7503	Approved
0.7236	Intermediate Similarity	NPD8379	Approved
0.7236	Intermediate Similarity	NPD8296	Approved
0.7222	Intermediate Similarity	NPD7637	Suspended
0.7217	Intermediate Similarity	NPD4767	Approved
0.7217	Intermediate Similarity	NPD4768	Approved
0.7213	Intermediate Similarity	NPD7516	Approved
0.7207	Intermediate Similarity	NPD5173	Approved
0.7184	Intermediate Similarity	NPD4223	Phase 3
0.7184	Intermediate Similarity	NPD4221	Approved
0.7184	Intermediate Similarity	NPD3667	Approved
0.7182	Intermediate Similarity	NPD5210	Approved
0.7182	Intermediate Similarity	NPD4629	Approved
0.7143	Intermediate Similarity	NPD5329	Approved
0.7143	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5169	Approved
0.7119	Intermediate Similarity	NPD5249	Phase 3
0.7119	Intermediate Similarity	NPD5250	Approved
0.7119	Intermediate Similarity	NPD5251	Approved
0.7119	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5247	Approved
0.7119	Intermediate Similarity	NPD5248	Approved
0.7119	Intermediate Similarity	NPD5135	Approved
0.7117	Intermediate Similarity	NPD4697	Phase 3
0.7107	Intermediate Similarity	NPD6868	Approved
0.7105	Intermediate Similarity	NPD7632	Discontinued
0.7103	Intermediate Similarity	NPD5208	Approved
0.7094	Intermediate Similarity	NPD5128	Approved
0.7075	Intermediate Similarity	NPD6098	Approved
0.7075	Intermediate Similarity	NPD5280	Approved
0.7075	Intermediate Similarity	NPD5279	Phase 3
0.7075	Intermediate Similarity	NPD4694	Approved
0.7064	Intermediate Similarity	NPD5693	Phase 1
0.7059	Intermediate Similarity	NPD5217	Approved
0.7059	Intermediate Similarity	NPD5127	Approved
0.7059	Intermediate Similarity	NPD5216	Approved
0.7059	Intermediate Similarity	NPD5215	Approved
0.7048	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4197	Approved
0.7034	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7524	Approved
0.6991	Remote Similarity	NPD4225	Approved
0.699	Remote Similarity	NPD7525	Registered
0.6952	Remote Similarity	NPD6695	Phase 3
0.6952	Remote Similarity	NPD4788	Approved
0.6952	Remote Similarity	NPD5362	Discontinued
0.6949	Remote Similarity	NPD6686	Approved
0.6942	Remote Similarity	NPD8133	Approved
0.6935	Remote Similarity	NPD4522	Approved
0.6931	Remote Similarity	NPD6933	Approved
0.6923	Remote Similarity	NPD5369	Approved
0.6916	Remote Similarity	NPD4690	Approved
0.6916	Remote Similarity	NPD4693	Phase 3
0.6916	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4138	Approved
0.6916	Remote Similarity	NPD5205	Approved
0.6916	Remote Similarity	NPD4689	Approved
0.6916	Remote Similarity	NPD4688	Approved
0.6916	Remote Similarity	NPD5690	Phase 2
0.6909	Remote Similarity	NPD6411	Approved
0.6891	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5167	Approved
0.6875	Remote Similarity	NPD5654	Approved
0.6857	Remote Similarity	NPD6435	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