NPASS Compound

Structure

NPC474550 OpenBabel07101719252D 43 45 0 0 1 0 0 0 0 0999 V2000 5.5685 3.4487 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 -1.5804 -4.9086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5733 3.0134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7138 4.1723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3802 2.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1906 -1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0685 2.5827 0.0000 C 0 0 0 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 -1.8029 -3.9337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0685 2.5827 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 -1.0698 -3.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 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 0.4048 3.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6906 -0.3660 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 2.0685 2.5827 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 3.5685 3.4487 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 -1.2924 -2.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 1 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 -1.7568 -0.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1906 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7818 -0.6235 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 -4.6906 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0685 4.3147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2479 -1.9838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3802 -1.1828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1906 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5685 3.4487 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 -0.5593 -1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 19 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 17 34 1 0 0 0 0 18 24 1 0 0 0 0 18 33 1 0 0 0 0 20 31 1 0 0 0 0 21 35 2 0 0 0 0 21 40 1 0 0 0 0 22 29 1 0 0 0 0 22 33 1 6 0 0 0 23 28 1 0 0 0 0 23 41 1 1 0 0 0 24 34 1 1 0 0 0 24 42 1 0 0 0 0 25 36 2 0 0 0 0 25 41 1 0 0 0 0 26 37 2 0 0 0 0 26 42 1 0 0 0 0 27 38 2 0 0 0 0 27 43 1 0 0 0 0 28 19 1 1 0 0 0 28 29 1 0 0 0 0 29 34 1 1 0 0 0 30 31 1 0 0 0 0 30 32 1 0 0 0 0 30 39 1 1 0 0 0 31 40 1 1 0 0 0 32 33 1 6 0 0 0 32 43 1 0 0 0 0 33 8 1 6 0 0 0 34 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	606.38
Volume:	636.88
LogP:	5.765
LogD:	4.649
LogS:	-5.143
# Rotatable Bonds:	15
TPSA:	125.43
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.179
Synthetic Accessibility Score:	5.266
Fsp3:	0.824
Lipinski Rule-of-5:	Rejected
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:	-4.736
MDCK Permeability:	4.143535625189543e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.689
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	89.04120635986328%
Volume Distribution (VD):	0.904
Pgp-substrate:	2.699662446975708%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.039
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.525
CYP2C9-inhibitor:	0.211
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.614
CYP3A4-substrate:	0.418

ADMET: Excretion

Clearance (CL):	9.892
Half-life (T1/2):	0.402

ADMET: Toxicity

hERG Blockers:	0.153
Human Hepatotoxicity (H-HT):	0.67
Drug-inuced Liver Injury (DILI):	0.89
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.737
Carcinogencity:	0.05
Eye Corrosion:	0.009
Eye Irritation:	0.022
Respiratory Toxicity:	0.75

Download Data

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

Natural Product: NPC474550

Natural Product ID:	NPC474550
*Common Name:**	Gagunin F
IUPAC Name:	[(1R,2S,3aR,4S,5aR,6S,7S,8S,10aR,10bS)-8-acetyloxy-4,6-di(butanoyloxy)-7-hydroxy-3a,5a,9-trimethyl-1-propan-2-yl-1,2,3,4,5,6,7,8,10a,10b-decahydrocyclohepta[e]inden-2-yl] butanoate
Synonyms:	Gagunin F
Standard InCHIKey:	XYWGGCAKJMPSFJ-VJHQNTRZSA-N
Standard InCHI:	InChI=1S/C34H54O9/c1-10-13-25(36)41-23-17-34(9)24(42-26(37)14-11-2)18-33(8)22(29(34)28(23)19(4)5)16-20(6)31(40-21(7)35)30(39)32(33)43-27(38)15-12-3/h16,19,22-24,28-32,39H,10-15,17-18H2,1-9H3/t22-,23+,24+,28+,29+,30+,31+,32-,33-,34+/m1/s1
SMILES:	CCCC(=O)OC1CC2(C(CC3(C(C2C1C(C)C)C=C(C(C(C3OC(=O)CCC)O)OC(=O)C)C)C)OC(=O)CCC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471798
PubChem CID:	11114711
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32676	phorbas sp.	Species	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18811205]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	0.25	ug.mL-1	PMID[474082]
NPT2	Others	Unspecified		LC50	=	55.0	ug.mL-1	PMID[474082]

☑ 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 NPC474550 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	1260
0.2-0.3	4299
0.3-0.4	9501
0.4-0.5	12201
0.5-0.6	6160
0.6-0.7	6664
0.7-0.8	2296
0.8-0.85	97
0.85-0.9	5
0.9-0.95	1
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475585
1.0	High Similarity	NPC473577
0.9897	High Similarity	NPC475290
0.9691	High Similarity	NPC473694
0.9691	High Similarity	NPC475623
0.9691	High Similarity	NPC475334
0.9592	High Similarity	NPC201144
0.9592	High Similarity	NPC475335
0.9592	High Similarity	NPC80809
0.9592	High Similarity	NPC181104
0.9592	High Similarity	NPC288502
0.9592	High Similarity	NPC103298
0.9592	High Similarity	NPC121518
0.9592	High Similarity	NPC475331
0.9495	High Similarity	NPC60315
0.8911	High Similarity	NPC474124
0.8812	High Similarity	NPC476471
0.8812	High Similarity	NPC475344
0.8738	High Similarity	NPC470980
0.8713	High Similarity	NPC475617
0.8641	High Similarity	NPC473543
0.8627	High Similarity	NPC470972
0.8571	High Similarity	NPC88701
0.8544	High Similarity	NPC473523
0.85	High Similarity	NPC475304
0.8491	Intermediate Similarity	NPC173905
0.8491	Intermediate Similarity	NPC5475
0.8491	Intermediate Similarity	NPC284828
0.8491	Intermediate Similarity	NPC472216
0.844	Intermediate Similarity	NPC43213
0.844	Intermediate Similarity	NPC216665
0.8431	Intermediate Similarity	NPC473510
0.8431	Intermediate Similarity	NPC230546
0.8416	Intermediate Similarity	NPC254121
0.8416	Intermediate Similarity	NPC475032
0.8416	Intermediate Similarity	NPC475033
0.8411	Intermediate Similarity	NPC475563
0.8411	Intermediate Similarity	NPC475134
0.835	Intermediate Similarity	NPC155974
0.8333	Intermediate Similarity	NPC475668
0.8333	Intermediate Similarity	NPC470076
0.8333	Intermediate Similarity	NPC475480
0.8333	Intermediate Similarity	NPC473921
0.8318	Intermediate Similarity	NPC40728
0.8317	Intermediate Similarity	NPC88009
0.8273	Intermediate Similarity	NPC178289
0.8269	Intermediate Similarity	NPC472552
0.8269	Intermediate Similarity	NPC200672
0.8269	Intermediate Similarity	NPC214714
0.8252	Intermediate Similarity	NPC272223
0.8252	Intermediate Similarity	NPC208358
0.8241	Intermediate Similarity	NPC238850
0.8235	Intermediate Similarity	NPC210337
0.8235	Intermediate Similarity	NPC274793
0.8224	Intermediate Similarity	NPC48548
0.8224	Intermediate Similarity	NPC217921
0.8224	Intermediate Similarity	NPC135015
0.8224	Intermediate Similarity	NPC472218
0.8224	Intermediate Similarity	NPC472217
0.8224	Intermediate Similarity	NPC128795
0.8224	Intermediate Similarity	NPC472219
0.8218	Intermediate Similarity	NPC292178
0.8218	Intermediate Similarity	NPC86893
0.8208	Intermediate Similarity	NPC119855
0.8208	Intermediate Similarity	NPC220217
0.8198	Intermediate Similarity	NPC470075
0.819	Intermediate Similarity	NPC474775
0.819	Intermediate Similarity	NPC472821
0.8174	Intermediate Similarity	NPC129992
0.8173	Intermediate Similarity	NPC289670
0.8173	Intermediate Similarity	NPC26557
0.8173	Intermediate Similarity	NPC472554
0.8155	Intermediate Similarity	NPC470066
0.8155	Intermediate Similarity	NPC470067
0.8148	Intermediate Similarity	NPC316974
0.8142	Intermediate Similarity	NPC5883
0.8142	Intermediate Similarity	NPC304260
0.8142	Intermediate Similarity	NPC44899
0.8142	Intermediate Similarity	NPC29639
0.8142	Intermediate Similarity	NPC472667
0.8137	Intermediate Similarity	NPC129569
0.8137	Intermediate Similarity	NPC304899
0.8137	Intermediate Similarity	NPC284194
0.8137	Intermediate Similarity	NPC471765
0.8137	Intermediate Similarity	NPC221801
0.8137	Intermediate Similarity	NPC211810
0.8137	Intermediate Similarity	NPC253115
0.8131	Intermediate Similarity	NPC475781
0.8131	Intermediate Similarity	NPC469318
0.8131	Intermediate Similarity	NPC88013
0.8131	Intermediate Similarity	NPC473173
0.8131	Intermediate Similarity	NPC125423
0.8131	Intermediate Similarity	NPC473586
0.8125	Intermediate Similarity	NPC93883
0.8125	Intermediate Similarity	NPC203862
0.8119	Intermediate Similarity	NPC182826
0.8119	Intermediate Similarity	NPC472416
0.8119	Intermediate Similarity	NPC473258
0.8119	Intermediate Similarity	NPC474922
0.8119	Intermediate Similarity	NPC105375
0.8119	Intermediate Similarity	NPC472360
0.8113	Intermediate Similarity	NPC152966
0.81	Intermediate Similarity	NPC234335
0.8095	Intermediate Similarity	NPC474709
0.8095	Intermediate Similarity	NPC252242
0.8095	Intermediate Similarity	NPC475956
0.8095	Intermediate Similarity	NPC165578
0.8091	Intermediate Similarity	NPC470063
0.8087	Intermediate Similarity	NPC257017
0.8087	Intermediate Similarity	NPC162009
0.8081	Intermediate Similarity	NPC246028
0.8077	Intermediate Similarity	NPC38855
0.8077	Intermediate Similarity	NPC274643
0.8077	Intermediate Similarity	NPC251680
0.8073	Intermediate Similarity	NPC472215
0.8073	Intermediate Similarity	NPC472214
0.8073	Intermediate Similarity	NPC181298
0.8058	Intermediate Similarity	NPC473244
0.8056	Intermediate Similarity	NPC475263
0.8056	Intermediate Similarity	NPC311223
0.8053	Intermediate Similarity	NPC146280
0.8053	Intermediate Similarity	NPC124676
0.8053	Intermediate Similarity	NPC475372
0.8039	Intermediate Similarity	NPC476720
0.8039	Intermediate Similarity	NPC471786
0.8039	Intermediate Similarity	NPC37603
0.8037	Intermediate Similarity	NPC173172
0.8037	Intermediate Similarity	NPC186668
0.8037	Intermediate Similarity	NPC475414
0.8036	Intermediate Similarity	NPC310341
0.8036	Intermediate Similarity	NPC99620
0.8036	Intermediate Similarity	NPC193382
0.8036	Intermediate Similarity	NPC207637
0.8036	Intermediate Similarity	NPC199428
0.8036	Intermediate Similarity	NPC5311
0.8036	Intermediate Similarity	NPC138372
0.8036	Intermediate Similarity	NPC106228
0.802	Intermediate Similarity	NPC99653
0.8019	Intermediate Similarity	NPC474783
0.8019	Intermediate Similarity	NPC475889
0.8019	Intermediate Similarity	NPC7644
0.8019	Intermediate Similarity	NPC127933
0.8019	Intermediate Similarity	NPC189588
0.8019	Intermediate Similarity	NPC232515
0.8019	Intermediate Similarity	NPC196471
0.8019	Intermediate Similarity	NPC7613
0.8019	Intermediate Similarity	NPC10232
0.8019	Intermediate Similarity	NPC85742
0.8019	Intermediate Similarity	NPC97487
0.8019	Intermediate Similarity	NPC187302
0.8019	Intermediate Similarity	NPC160583
0.8019	Intermediate Similarity	NPC260809
0.8	Intermediate Similarity	NPC476132
0.8	Intermediate Similarity	NPC52839
0.8	Intermediate Similarity	NPC114188
0.8	Intermediate Similarity	NPC11974
0.8	Intermediate Similarity	NPC247701
0.8	Intermediate Similarity	NPC268829
0.8	Intermediate Similarity	NPC25177
0.8	Intermediate Similarity	NPC49532
0.8	Intermediate Similarity	NPC470832
0.8	Intermediate Similarity	NPC231518
0.8	Intermediate Similarity	NPC475219
0.8	Intermediate Similarity	NPC295110
0.8	Intermediate Similarity	NPC222875
0.7982	Intermediate Similarity	NPC5292
0.7982	Intermediate Similarity	NPC475041
0.7982	Intermediate Similarity	NPC236973
0.7982	Intermediate Similarity	NPC292467
0.7982	Intermediate Similarity	NPC30483
0.7982	Intermediate Similarity	NPC470897
0.7982	Intermediate Similarity	NPC469380
0.7982	Intermediate Similarity	NPC312536
0.7982	Intermediate Similarity	NPC475274
0.7982	Intermediate Similarity	NPC218853
0.7982	Intermediate Similarity	NPC477071
0.7982	Intermediate Similarity	NPC42662
0.7982	Intermediate Similarity	NPC469756
0.7982	Intermediate Similarity	NPC32177
0.7982	Intermediate Similarity	NPC9674
0.7982	Intermediate Similarity	NPC55532
0.7982	Intermediate Similarity	NPC19028
0.7981	Intermediate Similarity	NPC470068
0.7981	Intermediate Similarity	NPC102426
0.7981	Intermediate Similarity	NPC474957
0.7981	Intermediate Similarity	NPC79449
0.7981	Intermediate Similarity	NPC300179
0.7965	Intermediate Similarity	NPC471353
0.7965	Intermediate Similarity	NPC471355
0.7965	Intermediate Similarity	NPC34390
0.7965	Intermediate Similarity	NPC158344
0.7965	Intermediate Similarity	NPC473656
0.7965	Intermediate Similarity	NPC471354
0.7965	Intermediate Similarity	NPC196429
0.7965	Intermediate Similarity	NPC10721
0.7965	Intermediate Similarity	NPC474418
0.7965	Intermediate Similarity	NPC471351
0.7965	Intermediate Similarity	NPC27507
0.7965	Intermediate Similarity	NPC142066
0.7965	Intermediate Similarity	NPC77319

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 NPC474550 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1616
0.2-0.3	3821
0.3-0.4	2346
0.4-0.5	711
0.5-0.6	242
0.6-0.7	219
0.7-0.8	31
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8155	Intermediate Similarity	NPD7638	Approved
0.8077	Intermediate Similarity	NPD7640	Approved
0.8077	Intermediate Similarity	NPD7639	Approved
0.8	Intermediate Similarity	NPD8033	Approved
0.7913	Intermediate Similarity	NPD8377	Approved
0.7913	Intermediate Similarity	NPD8294	Approved
0.7895	Intermediate Similarity	NPD7327	Approved
0.7895	Intermediate Similarity	NPD7328	Approved
0.7845	Intermediate Similarity	NPD8380	Approved
0.7845	Intermediate Similarity	NPD8335	Approved
0.7845	Intermediate Similarity	NPD8379	Approved
0.7845	Intermediate Similarity	NPD8378	Approved
0.7845	Intermediate Similarity	NPD8296	Approved
0.7826	Intermediate Similarity	NPD7516	Approved
0.7731	Intermediate Similarity	NPD7507	Approved
0.7642	Intermediate Similarity	NPD4225	Approved
0.7542	Intermediate Similarity	NPD7503	Approved
0.7541	Intermediate Similarity	NPD7319	Approved
0.7456	Intermediate Similarity	NPD8297	Approved
0.7434	Intermediate Similarity	NPD6371	Approved
0.7431	Intermediate Similarity	NPD7632	Discontinued
0.7411	Intermediate Similarity	NPD6686	Approved
0.7391	Intermediate Similarity	NPD8133	Approved
0.735	Intermediate Similarity	NPD7115	Discovery
0.7339	Intermediate Similarity	NPD5344	Discontinued
0.7321	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6319	Approved
0.7308	Intermediate Similarity	NPD46	Approved
0.7308	Intermediate Similarity	NPD6698	Approved
0.7308	Intermediate Similarity	NPD7838	Discovery
0.7304	Intermediate Similarity	NPD6053	Discontinued
0.7241	Intermediate Similarity	NPD4632	Approved
0.7238	Intermediate Similarity	NPD7637	Suspended
0.7232	Intermediate Similarity	NPD5739	Approved
0.7232	Intermediate Similarity	NPD7128	Approved
0.7232	Intermediate Similarity	NPD6402	Approved
0.7232	Intermediate Similarity	NPD6675	Approved
0.7193	Intermediate Similarity	NPD6372	Approved
0.7193	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6373	Approved
0.717	Intermediate Similarity	NPD6399	Phase 3
0.7168	Intermediate Similarity	NPD6412	Phase 2
0.7157	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6899	Approved
0.7105	Intermediate Similarity	NPD7320	Approved
0.7105	Intermediate Similarity	NPD6881	Approved
0.7069	Intermediate Similarity	NPD6649	Approved
0.7069	Intermediate Similarity	NPD8130	Phase 1
0.7069	Intermediate Similarity	NPD6650	Approved
0.7048	Intermediate Similarity	NPD6051	Approved
0.7019	Intermediate Similarity	NPD4250	Approved
0.7019	Intermediate Similarity	NPD4251	Approved
0.7019	Intermediate Similarity	NPD7524	Approved
0.7018	Intermediate Similarity	NPD5701	Approved
0.7018	Intermediate Similarity	NPD5697	Approved
0.7009	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7290	Approved
0.6983	Remote Similarity	NPD6883	Approved
0.6983	Remote Similarity	NPD7102	Approved
0.696	Remote Similarity	NPD8293	Discontinued
0.6937	Remote Similarity	NPD6648	Approved
0.6935	Remote Similarity	NPD7492	Approved
0.693	Remote Similarity	NPD6008	Approved
0.6923	Remote Similarity	NPD6869	Approved
0.6923	Remote Similarity	NPD6847	Approved
0.6923	Remote Similarity	NPD4249	Approved
0.6923	Remote Similarity	NPD6617	Approved
0.6917	Remote Similarity	NPD6009	Approved
0.6916	Remote Similarity	NPD8034	Phase 2
0.6916	Remote Similarity	NPD8035	Phase 2
0.6916	Remote Similarity	NPD7983	Approved
0.6909	Remote Similarity	NPD6083	Phase 2
0.6909	Remote Similarity	NPD6084	Phase 2
0.6905	Remote Similarity	NPD7736	Approved
0.6897	Remote Similarity	NPD6014	Approved
0.6897	Remote Similarity	NPD6013	Approved
0.6897	Remote Similarity	NPD6012	Approved
0.6897	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6054	Approved
0.6885	Remote Similarity	NPD6059	Approved
0.688	Remote Similarity	NPD6616	Approved
0.6855	Remote Similarity	NPD7604	Phase 2
0.6832	Remote Similarity	NPD4819	Approved
0.6832	Remote Similarity	NPD4821	Approved
0.6832	Remote Similarity	NPD4822	Approved
0.6832	Remote Similarity	NPD7525	Registered
0.6832	Remote Similarity	NPD4820	Approved
0.6829	Remote Similarity	NPD5983	Phase 2
0.6825	Remote Similarity	NPD7078	Approved
0.681	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6011	Approved
0.68	Remote Similarity	NPD4268	Approved
0.68	Remote Similarity	NPD4271	Approved
0.6796	Remote Similarity	NPD6695	Phase 3
0.6796	Remote Similarity	NPD5362	Discontinued
0.678	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6370	Approved
0.6757	Remote Similarity	NPD4755	Approved
0.6746	Remote Similarity	NPD6336	Discontinued
0.6731	Remote Similarity	NPD4786	Approved
0.6727	Remote Similarity	NPD5695	Phase 3
0.6724	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7750	Discontinued
0.6698	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4202	Approved
0.6696	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4634	Approved
0.6694	Remote Similarity	NPD8515	Approved
0.6694	Remote Similarity	NPD8513	Phase 3
0.6694	Remote Similarity	NPD6015	Approved
0.6694	Remote Similarity	NPD8517	Approved
0.6694	Remote Similarity	NPD6016	Approved
0.6694	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5785	Approved
0.664	Remote Similarity	NPD5988	Approved
0.6639	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4696	Approved
0.6637	Remote Similarity	NPD5285	Approved
0.6637	Remote Similarity	NPD4700	Approved
0.6637	Remote Similarity	NPD5286	Approved
0.6636	Remote Similarity	NPD7748	Approved
0.6635	Remote Similarity	NPD5332	Approved
0.6635	Remote Similarity	NPD5331	Approved
0.6607	Remote Similarity	NPD7902	Approved
0.6604	Remote Similarity	NPD7334	Approved
0.6604	Remote Similarity	NPD6409	Approved
0.6604	Remote Similarity	NPD5330	Approved
0.6604	Remote Similarity	NPD7521	Approved
0.6604	Remote Similarity	NPD7146	Approved
0.6604	Remote Similarity	NPD6684	Approved
0.6602	Remote Similarity	NPD4790	Discontinued
0.66	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD8328	Phase 3
0.6579	Remote Similarity	NPD4159	Approved
0.6574	Remote Similarity	NPD5328	Approved
0.6569	Remote Similarity	NPD6929	Approved
0.6557	Remote Similarity	NPD6274	Approved
0.6552	Remote Similarity	NPD5141	Approved
0.6549	Remote Similarity	NPD5696	Approved
0.6545	Remote Similarity	NPD5779	Approved
0.6545	Remote Similarity	NPD5778	Approved
0.6538	Remote Similarity	NPD3667	Approved
0.6538	Remote Similarity	NPD6435	Approved
0.6532	Remote Similarity	NPD7100	Approved
0.6532	Remote Similarity	NPD7101	Approved
0.6522	Remote Similarity	NPD5225	Approved
0.6522	Remote Similarity	NPD4633	Approved
0.6522	Remote Similarity	NPD5224	Approved
0.6522	Remote Similarity	NPD5226	Approved
0.6505	Remote Similarity	NPD6931	Approved
0.6505	Remote Similarity	NPD6930	Phase 2
0.65	Remote Similarity	NPD6942	Approved
0.65	Remote Similarity	NPD7339	Approved
0.6496	Remote Similarity	NPD4768	Approved
0.6496	Remote Similarity	NPD4767	Approved
0.6481	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6903	Approved
0.6476	Remote Similarity	NPD7154	Phase 3
0.6471	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5175	Approved
0.6466	Remote Similarity	NPD5174	Approved
0.6457	Remote Similarity	NPD6067	Discontinued
0.6455	Remote Similarity	NPD7515	Phase 2
0.6455	Remote Similarity	NPD5693	Phase 1
0.6455	Remote Similarity	NPD6079	Approved
0.6452	Remote Similarity	NPD6335	Approved
0.6449	Remote Similarity	NPD3618	Phase 1
0.6436	Remote Similarity	NPD6933	Approved
0.6435	Remote Similarity	NPD5223	Approved
0.6434	Remote Similarity	NPD8074	Phase 3
0.6429	Remote Similarity	NPD6908	Approved
0.6429	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6909	Approved
0.6422	Remote Similarity	NPD4753	Phase 2
0.6422	Remote Similarity	NPD1695	Approved
0.6415	Remote Similarity	NPD3666	Approved
0.6415	Remote Similarity	NPD3665	Phase 1
0.6415	Remote Similarity	NPD3133	Approved
0.6387	Remote Similarity	NPD4729	Approved
0.6387	Remote Similarity	NPD4730	Approved
0.6385	Remote Similarity	NPD6033	Approved
0.6381	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4269	Approved
0.6381	Remote Similarity	NPD4270	Approved
0.6373	Remote Similarity	NPD5776	Phase 2
0.6373	Remote Similarity	NPD6925	Approved
0.6371	Remote Similarity	NPD6317	Approved
0.6364	Remote Similarity	NPD7260	Phase 2
0.6346	Remote Similarity	NPD7514	Phase 3
0.6346	Remote Similarity	NPD5368	Approved
0.6339	Remote Similarity	NPD7900	Approved
0.6339	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5737	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