NPASS Compound

Structure

NPC257082 OpenBabel07101718202D 37 41 0 0 1 0 0 0 0 0999 V2000 8.1038 1.3806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8959 2.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 -0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1340 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5054 2.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 2.9680 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4836 2.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 3.5032 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 3.8581 2.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 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 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 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 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1527 1.6896 0.0000 C 0 0 0 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 2.5981 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 2 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4980 4.4543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8437 0.7386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 6 37 1 0 0 0 0 7 8 1 0 0 0 0 7 12 2 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 30 1 0 0 0 0 16 23 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 32 2 0 0 0 0 18 30 1 0 0 0 0 19 8 1 6 0 0 0 19 20 1 0 0 0 0 20 27 1 1 0 0 0 21 28 1 6 0 0 0 21 30 1 0 0 0 0 22 29 1 1 0 0 0 22 31 1 0 0 0 0 23 29 1 1 0 0 0 23 33 1 0 0 0 0 24 31 1 6 0 0 0 24 34 1 0 0 0 0 25 29 1 0 0 0 0 25 35 2 0 0 0 0 25 37 1 0 0 0 0 26 36 1 0 0 0 0 27 28 1 1 0 0 0 28 4 1 6 0 0 0 29 5 1 1 0 0 0 30 31 1 6 0 0 0 31 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.35
Volume:	546.782
LogP:	2.681
LogD:	2.757
LogS:	-4.252
# Rotatable Bonds:	7
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.274
Synthetic Accessibility Score:	6.257
Fsp3:	0.871
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.278
MDCK Permeability:	1.3721078175876755e-05
Pgp-inhibitor:	0.162
Pgp-substrate:	0.945
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.947
Plasma Protein Binding (PPB):	71.62517547607422%
Volume Distribution (VD):	0.596
Pgp-substrate:	19.230144500732422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.405
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.684
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.944
CYP3A4-substrate:	0.447

ADMET: Excretion

Clearance (CL):	5.533
Half-life (T1/2):	0.501

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.612
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.609
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.945
Carcinogencity:	0.865
Eye Corrosion:	0.009
Eye Irritation:	0.015
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: NPC257082

Natural Product ID:	NPC257082
*Common Name:**	TYVLOHFZVJSLIQ-RYSSIURDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TYVLOHFZVJSLIQ-RYSSIURDSA-N
Standard InCHI:	InChI=1S/C31H48O6/c1-26(2,36)12-7-8-19(17-32)20-11-13-28(4)21-9-10-22-29(5,25(35)37-6)23(33)16-24(34)31(22)18-30(21,31)15-14-27(20,28)3/h7,12,17,19-24,33-34,36H,8-11,13-16,18H2,1-6H3/b12-7+/t19-,20+,21-,22-,23-,24-,27+,28-,29-,30-,31+/m0/s1
SMILES:	O=C[C@@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)[C@@H](O)C[C@@H]([C@@]2(C)C(=O)OC)O)C)C/C=C/C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL117101
PubChem CID:	44344717
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	43.79	uM	PMID[486075]

☑ 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 NPC257082 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	1405
0.2-0.3	4664
0.3-0.4	9344
0.4-0.5	12423
0.5-0.6	6448
0.6-0.7	5978
0.7-0.8	2108
0.8-0.85	93
0.85-0.9	14
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9802	High Similarity	NPC285298
0.96	High Similarity	NPC201763
0.951	High Similarity	NPC163216
0.9412	High Similarity	NPC263729
0.901	High Similarity	NPC180733
0.901	High Similarity	NPC41971
0.901	High Similarity	NPC37047
0.8835	High Similarity	NPC193934
0.8835	High Similarity	NPC271980
0.875	High Similarity	NPC312900
0.875	High Similarity	NPC222153
0.8738	High Similarity	NPC75941
0.8727	High Similarity	NPC72772
0.8727	High Similarity	NPC469794
0.8641	High Similarity	NPC94906
0.8614	High Similarity	NPC263135
0.8614	High Similarity	NPC288906
0.8544	High Similarity	NPC472028
0.8544	High Similarity	NPC119036
0.8476	Intermediate Similarity	NPC124544
0.8431	Intermediate Similarity	NPC84383
0.8426	Intermediate Similarity	NPC472219
0.8426	Intermediate Similarity	NPC472217
0.8426	Intermediate Similarity	NPC472218
0.8421	Intermediate Similarity	NPC184555
0.8381	Intermediate Similarity	NPC477052
0.8381	Intermediate Similarity	NPC477053
0.8381	Intermediate Similarity	NPC477051
0.8365	Intermediate Similarity	NPC477854
0.8362	Intermediate Similarity	NPC55602
0.835	Intermediate Similarity	NPC234564
0.835	Intermediate Similarity	NPC327788
0.835	Intermediate Similarity	NPC160056
0.8302	Intermediate Similarity	NPC477054
0.8286	Intermediate Similarity	NPC477521
0.8252	Intermediate Similarity	NPC266899
0.8252	Intermediate Similarity	NPC279974
0.8235	Intermediate Similarity	NPC477855
0.8208	Intermediate Similarity	NPC71706
0.8173	Intermediate Similarity	NPC477853
0.8173	Intermediate Similarity	NPC114743
0.8173	Intermediate Similarity	NPC195366
0.8148	Intermediate Similarity	NPC29705
0.8142	Intermediate Similarity	NPC238667
0.8125	Intermediate Similarity	NPC90952
0.8113	Intermediate Similarity	NPC470074
0.8113	Intermediate Similarity	NPC471041
0.8103	Intermediate Similarity	NPC476962
0.8095	Intermediate Similarity	NPC469810
0.8095	Intermediate Similarity	NPC253586
0.8095	Intermediate Similarity	NPC156546
0.8077	Intermediate Similarity	NPC266431
0.8073	Intermediate Similarity	NPC37600
0.807	Intermediate Similarity	NPC196931
0.807	Intermediate Similarity	NPC270929
0.8067	Intermediate Similarity	NPC293112
0.8051	Intermediate Similarity	NPC11895
0.8051	Intermediate Similarity	NPC469789
0.8037	Intermediate Similarity	NPC121218
0.8037	Intermediate Similarity	NPC282524
0.8037	Intermediate Similarity	NPC46848
0.8037	Intermediate Similarity	NPC253886
0.8037	Intermediate Similarity	NPC289670
0.8037	Intermediate Similarity	NPC472924
0.8036	Intermediate Similarity	NPC270586
0.802	Intermediate Similarity	NPC146937
0.8018	Intermediate Similarity	NPC472216
0.8018	Intermediate Similarity	NPC284828
0.8018	Intermediate Similarity	NPC173905
0.8018	Intermediate Similarity	NPC5475
0.8017	Intermediate Similarity	NPC476960
0.8	Intermediate Similarity	NPC474518
0.8	Intermediate Similarity	NPC329910
0.8	Intermediate Similarity	NPC54248
0.8	Intermediate Similarity	NPC476959
0.8	Intermediate Similarity	NPC472925
0.8	Intermediate Similarity	NPC276103
0.8	Intermediate Similarity	NPC29152
0.8	Intermediate Similarity	NPC302111
0.8	Intermediate Similarity	NPC59530
0.7983	Intermediate Similarity	NPC81736
0.7983	Intermediate Similarity	NPC172154
0.7983	Intermediate Similarity	NPC8369
0.7983	Intermediate Similarity	NPC233041
0.7982	Intermediate Similarity	NPC72255
0.7982	Intermediate Similarity	NPC470953
0.7982	Intermediate Similarity	NPC471293
0.7982	Intermediate Similarity	NPC474281
0.7982	Intermediate Similarity	NPC475036
0.7981	Intermediate Similarity	NPC470385
0.7981	Intermediate Similarity	NPC292793
0.7981	Intermediate Similarity	NPC470386
0.7966	Intermediate Similarity	NPC170538
0.7965	Intermediate Similarity	NPC4573
0.7965	Intermediate Similarity	NPC277769
0.7963	Intermediate Similarity	NPC275990
0.7963	Intermediate Similarity	NPC475558
0.7963	Intermediate Similarity	NPC304832
0.7963	Intermediate Similarity	NPC473788
0.7963	Intermediate Similarity	NPC88203
0.7963	Intermediate Similarity	NPC76866
0.7963	Intermediate Similarity	NPC148628
0.7963	Intermediate Similarity	NPC246736
0.7963	Intermediate Similarity	NPC214946
0.7963	Intermediate Similarity	NPC286519
0.7961	Intermediate Similarity	NPC275671
0.7949	Intermediate Similarity	NPC154491
0.7949	Intermediate Similarity	NPC268530
0.7946	Intermediate Similarity	NPC472215
0.7946	Intermediate Similarity	NPC472214
0.7944	Intermediate Similarity	NPC218383
0.7944	Intermediate Similarity	NPC108371
0.7944	Intermediate Similarity	NPC251680
0.7941	Intermediate Similarity	NPC56962
0.7941	Intermediate Similarity	NPC24705
0.7941	Intermediate Similarity	NPC128496
0.7941	Intermediate Similarity	NPC475921
0.7941	Intermediate Similarity	NPC474704
0.7931	Intermediate Similarity	NPC329736
0.7925	Intermediate Similarity	NPC190080
0.7925	Intermediate Similarity	NPC126815
0.7925	Intermediate Similarity	NPC472851
0.7925	Intermediate Similarity	NPC111187
0.7913	Intermediate Similarity	NPC179626
0.7913	Intermediate Similarity	NPC476963
0.7913	Intermediate Similarity	NPC298278
0.7909	Intermediate Similarity	NPC278628
0.7909	Intermediate Similarity	NPC80566
0.7909	Intermediate Similarity	NPC295366
0.7909	Intermediate Similarity	NPC472655
0.7909	Intermediate Similarity	NPC231530
0.7905	Intermediate Similarity	NPC476174
0.7905	Intermediate Similarity	NPC470229
0.7905	Intermediate Similarity	NPC470232
0.7895	Intermediate Similarity	NPC312017
0.7895	Intermediate Similarity	NPC73050
0.7895	Intermediate Similarity	NPC9848
0.7895	Intermediate Similarity	NPC122056
0.7895	Intermediate Similarity	NPC962
0.7895	Intermediate Similarity	NPC472926
0.789	Intermediate Similarity	NPC249187
0.789	Intermediate Similarity	NPC247957
0.789	Intermediate Similarity	NPC469985
0.789	Intermediate Similarity	NPC95899
0.789	Intermediate Similarity	NPC120321
0.789	Intermediate Similarity	NPC90177
0.789	Intermediate Similarity	NPC478057
0.789	Intermediate Similarity	NPC112009
0.789	Intermediate Similarity	NPC36688
0.789	Intermediate Similarity	NPC72151
0.789	Intermediate Similarity	NPC475050
0.7885	Intermediate Similarity	NPC477520
0.7885	Intermediate Similarity	NPC476304
0.7881	Intermediate Similarity	NPC67569
0.7881	Intermediate Similarity	NPC4021
0.7881	Intermediate Similarity	NPC159456
0.787	Intermediate Similarity	NPC52899
0.787	Intermediate Similarity	NPC471412
0.787	Intermediate Similarity	NPC163963
0.787	Intermediate Similarity	NPC476897
0.787	Intermediate Similarity	NPC295276
0.787	Intermediate Similarity	NPC289148
0.7869	Intermediate Similarity	NPC89514
0.7869	Intermediate Similarity	NPC17896
0.7869	Intermediate Similarity	NPC219085
0.7869	Intermediate Similarity	NPC70542
0.7869	Intermediate Similarity	NPC9499
0.7869	Intermediate Similarity	NPC6108
0.7869	Intermediate Similarity	NPC469752
0.7869	Intermediate Similarity	NPC86159
0.7869	Intermediate Similarity	NPC251866
0.7869	Intermediate Similarity	NPC471358
0.7869	Intermediate Similarity	NPC471360
0.7869	Intermediate Similarity	NPC469755
0.7869	Intermediate Similarity	NPC284406
0.7869	Intermediate Similarity	NPC471352
0.7869	Intermediate Similarity	NPC471361
0.7869	Intermediate Similarity	NPC471359
0.7869	Intermediate Similarity	NPC469751
0.7869	Intermediate Similarity	NPC180079
0.7869	Intermediate Similarity	NPC10823
0.7869	Intermediate Similarity	NPC469754
0.7869	Intermediate Similarity	NPC469753
0.7869	Intermediate Similarity	NPC197707
0.7864	Intermediate Similarity	NPC169933
0.7864	Intermediate Similarity	NPC469400
0.7863	Intermediate Similarity	NPC230513
0.7863	Intermediate Similarity	NPC61520
0.7863	Intermediate Similarity	NPC472933
0.7857	Intermediate Similarity	NPC474901
0.7857	Intermediate Similarity	NPC475941
0.7857	Intermediate Similarity	NPC474243
0.7851	Intermediate Similarity	NPC473253
0.785	Intermediate Similarity	NPC20479
0.785	Intermediate Similarity	NPC191565
0.785	Intermediate Similarity	NPC38296
0.785	Intermediate Similarity	NPC474793
0.785	Intermediate Similarity	NPC98837
0.785	Intermediate Similarity	NPC471038
0.785	Intermediate Similarity	NPC300179

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 NPC257082 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	1666
0.2-0.3	3936
0.3-0.4	2217
0.4-0.5	656
0.5-0.6	213
0.6-0.7	210
0.7-0.8	73
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
0.7944	Intermediate Similarity	NPD7640	Approved
0.7944	Intermediate Similarity	NPD7639	Approved
0.7869	Intermediate Similarity	NPD7319	Approved
0.785	Intermediate Similarity	NPD7638	Approved
0.7692	Intermediate Similarity	NPD7115	Discovery
0.7623	Intermediate Similarity	NPD7507	Approved
0.7619	Intermediate Similarity	NPD7637	Suspended
0.7611	Intermediate Similarity	NPD6881	Approved
0.7611	Intermediate Similarity	NPD6899	Approved
0.7589	Intermediate Similarity	NPD6402	Approved
0.7589	Intermediate Similarity	NPD7128	Approved
0.7589	Intermediate Similarity	NPD5739	Approved
0.7589	Intermediate Similarity	NPD6675	Approved
0.7522	Intermediate Similarity	NPD5697	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.7478	Intermediate Similarity	NPD7290	Approved
0.7478	Intermediate Similarity	NPD6883	Approved
0.7478	Intermediate Similarity	NPD7102	Approved
0.7477	Intermediate Similarity	NPD5211	Phase 2
0.7456	Intermediate Similarity	NPD7320	Approved
0.7456	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6079	Approved
0.7436	Intermediate Similarity	NPD4632	Approved
0.7429	Intermediate Similarity	NPD5328	Approved
0.7414	Intermediate Similarity	NPD6869	Approved
0.7414	Intermediate Similarity	NPD8130	Phase 1
0.7414	Intermediate Similarity	NPD6617	Approved
0.7414	Intermediate Similarity	NPD6650	Approved
0.7414	Intermediate Similarity	NPD6649	Approved
0.7414	Intermediate Similarity	NPD6847	Approved
0.7398	Intermediate Similarity	NPD7492	Approved
0.7391	Intermediate Similarity	NPD6372	Approved
0.7391	Intermediate Similarity	NPD6373	Approved
0.7391	Intermediate Similarity	NPD6012	Approved
0.7391	Intermediate Similarity	NPD6014	Approved
0.7391	Intermediate Similarity	NPD6013	Approved
0.7383	Intermediate Similarity	NPD5778	Approved
0.7383	Intermediate Similarity	NPD5779	Approved
0.7379	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5701	Approved
0.736	Intermediate Similarity	NPD7736	Approved
0.7355	Intermediate Similarity	NPD6054	Approved
0.735	Intermediate Similarity	NPD8297	Approved
0.735	Intermediate Similarity	NPD6882	Approved
0.7345	Intermediate Similarity	NPD5141	Approved
0.7339	Intermediate Similarity	NPD4697	Phase 3
0.7339	Intermediate Similarity	NPD6616	Approved
0.7328	Intermediate Similarity	NPD4634	Approved
0.7321	Intermediate Similarity	NPD7632	Discontinued
0.7317	Intermediate Similarity	NPD7604	Phase 2
0.7304	Intermediate Similarity	NPD6011	Approved
0.7297	Intermediate Similarity	NPD5285	Approved
0.7297	Intermediate Similarity	NPD4696	Approved
0.7297	Intermediate Similarity	NPD5286	Approved
0.7281	Intermediate Similarity	NPD6008	Approved
0.728	Intermediate Similarity	NPD7078	Approved
0.7273	Intermediate Similarity	NPD4755	Approved
0.725	Intermediate Similarity	NPD6009	Approved
0.7236	Intermediate Similarity	NPD6370	Approved
0.7222	Intermediate Similarity	NPD6399	Phase 3
0.7213	Intermediate Similarity	NPD6059	Approved
0.72	Intermediate Similarity	NPD6114	Approved
0.72	Intermediate Similarity	NPD6118	Approved
0.72	Intermediate Similarity	NPD6697	Approved
0.72	Intermediate Similarity	NPD6115	Approved
0.7182	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5221	Approved
0.7182	Intermediate Similarity	NPD5222	Approved
0.7168	Intermediate Similarity	NPD4633	Approved
0.7168	Intermediate Similarity	NPD5224	Approved
0.7168	Intermediate Similarity	NPD5225	Approved
0.7168	Intermediate Similarity	NPD5226	Approved
0.7154	Intermediate Similarity	NPD6015	Approved
0.7154	Intermediate Similarity	NPD6016	Approved
0.7143	Intermediate Similarity	NPD4700	Approved
0.7143	Intermediate Similarity	NPD8293	Discontinued
0.713	Intermediate Similarity	NPD7515	Phase 2
0.713	Intermediate Similarity	NPD6411	Approved
0.713	Intermediate Similarity	NPD8034	Phase 2
0.713	Intermediate Similarity	NPD8035	Phase 2
0.7119	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5173	Approved
0.7117	Intermediate Similarity	NPD6083	Phase 2
0.7117	Intermediate Similarity	NPD6084	Phase 2
0.7115	Intermediate Similarity	NPD4786	Approved
0.7105	Intermediate Similarity	NPD5174	Approved
0.7105	Intermediate Similarity	NPD5175	Approved
0.7097	Intermediate Similarity	NPD5988	Approved
0.7094	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5223	Approved
0.7059	Intermediate Similarity	NPD7525	Registered
0.703	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5983	Phase 2
0.7	Intermediate Similarity	NPD6117	Approved
0.7	Intermediate Similarity	NPD7748	Approved
0.6992	Remote Similarity	NPD7100	Approved
0.6992	Remote Similarity	NPD7101	Approved
0.6981	Remote Similarity	NPD3618	Phase 1
0.6981	Remote Similarity	NPD5786	Approved
0.6944	Remote Similarity	NPD6101	Approved
0.6944	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6116	Phase 1
0.6929	Remote Similarity	NPD6336	Discontinued
0.6923	Remote Similarity	NPD3667	Approved
0.6917	Remote Similarity	NPD6053	Discontinued
0.6911	Remote Similarity	NPD7327	Approved
0.6911	Remote Similarity	NPD6335	Approved
0.6911	Remote Similarity	NPD7328	Approved
0.6909	Remote Similarity	NPD4202	Approved
0.6903	Remote Similarity	NPD4225	Approved
0.6891	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6274	Approved
0.6885	Remote Similarity	NPD6868	Approved
0.6864	Remote Similarity	NPD4729	Approved
0.6864	Remote Similarity	NPD4730	Approved
0.6857	Remote Similarity	NPD6695	Phase 3
0.6855	Remote Similarity	NPD7516	Approved
0.6838	Remote Similarity	NPD4768	Approved
0.6838	Remote Similarity	NPD4767	Approved
0.6829	Remote Similarity	NPD6317	Approved
0.6827	Remote Similarity	NPD6902	Approved
0.6814	Remote Similarity	NPD7902	Approved
0.681	Remote Similarity	NPD4754	Approved
0.68	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4753	Phase 2
0.6786	Remote Similarity	NPD5695	Phase 3
0.6774	Remote Similarity	NPD6313	Approved
0.6774	Remote Similarity	NPD6314	Approved
0.6772	Remote Similarity	NPD8328	Phase 3
0.6762	Remote Similarity	NPD4270	Approved
0.6762	Remote Similarity	NPD4269	Approved
0.6754	Remote Similarity	NPD5696	Approved
0.675	Remote Similarity	NPD5247	Approved
0.675	Remote Similarity	NPD5248	Approved
0.675	Remote Similarity	NPD5251	Approved
0.675	Remote Similarity	NPD5249	Phase 3
0.675	Remote Similarity	NPD5250	Approved
0.6746	Remote Similarity	NPD8380	Approved
0.6746	Remote Similarity	NPD8335	Approved
0.6746	Remote Similarity	NPD8379	Approved
0.6746	Remote Similarity	NPD8296	Approved
0.6746	Remote Similarity	NPD6921	Approved
0.6746	Remote Similarity	NPD6908	Approved
0.6746	Remote Similarity	NPD6909	Approved
0.6746	Remote Similarity	NPD8378	Approved
0.6733	Remote Similarity	NPD3703	Phase 2
0.6731	Remote Similarity	NPD6930	Phase 2
0.6731	Remote Similarity	NPD7514	Phase 3
0.6731	Remote Similarity	NPD6931	Approved
0.6727	Remote Similarity	NPD5785	Approved
0.6723	Remote Similarity	NPD6686	Approved
0.6723	Remote Similarity	NPD5128	Approved
0.6721	Remote Similarity	NPD8133	Approved
0.6698	Remote Similarity	NPD5362	Discontinued
0.6697	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5737	Approved
0.6697	Remote Similarity	NPD6672	Approved
0.6694	Remote Similarity	NPD5217	Approved
0.6694	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5215	Approved
0.6694	Remote Similarity	NPD5216	Approved
0.6692	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6639	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6412	Phase 2
0.6637	Remote Similarity	NPD4629	Approved
0.6637	Remote Similarity	NPD5210	Approved
0.6636	Remote Similarity	NPD3666	Approved
0.6636	Remote Similarity	NPD3665	Phase 1
0.6636	Remote Similarity	NPD3133	Approved
0.6635	Remote Similarity	NPD6929	Approved
0.6614	Remote Similarity	NPD8033	Approved
0.6614	Remote Similarity	NPD8517	Approved
0.6614	Remote Similarity	NPD8515	Approved
0.6614	Remote Similarity	NPD8516	Approved
0.6614	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD8513	Phase 3
0.6612	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5135	Approved
0.6612	Remote Similarity	NPD5169	Approved
0.6612	Remote Similarity	NPD6371	Approved
0.6606	Remote Similarity	NPD7524	Approved
0.6606	Remote Similarity	NPD7750	Discontinued
0.6606	Remote Similarity	NPD3573	Approved
0.6606	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6435	Approved
0.6583	Remote Similarity	NPD5168	Approved
0.6574	Remote Similarity	NPD5363	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