NPASS Compound

Structure

NPC263729 OpenBabel07101718302D 36 40 0 0 1 0 0 0 0 0999 V2000 4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5283 6.2824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7363 5.3042 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 4.4251 7.3074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4980 4.4543 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 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 4.4762 4.6622 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 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 2 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 4.7852 5.6132 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 -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 0.6340 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1161 6.3564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 7 36 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 26 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 30 1 0 0 0 0 17 23 1 0 0 0 0 17 24 1 0 0 0 0 18 30 1 0 0 0 0 19 1 1 1 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 32 1 0 0 0 0 24 31 1 6 0 0 0 24 33 1 0 0 0 0 25 29 1 0 0 0 0 25 34 2 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 28 1 1 0 0 0 28 5 1 6 0 0 0 29 6 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:	502.37
Volume:	540.628
LogP:	4.647
LogD:	4.043
LogS:	-3.812
# Rotatable Bonds:	6
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.398
Synthetic Accessibility Score:	6.112
Fsp3:	0.903
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:	-5.578
MDCK Permeability:	1.5232651094265748e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.537
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.614
Plasma Protein Binding (PPB):	95.7962417602539%
Volume Distribution (VD):	0.678
Pgp-substrate:	4.380073547363281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.529
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.07
CYP2C9-substrate:	0.223
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.415

ADMET: Excretion

Clearance (CL):	3.593
Half-life (T1/2):	0.559

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.615
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.797
Maximum Recommended Daily Dose:	0.841
Skin Sensitization:	0.896
Carcinogencity:	0.703
Eye Corrosion:	0.02
Eye Irritation:	0.017
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC263729

Natural Product ID:	NPC263729
*Common Name:**	Quadrangularic Acid J
IUPAC Name:	n.a.
Synonyms:	Quadrangularic Acid J
Standard InCHIKey:	CJMHKPWFQAETJT-JPBBCIATSA-N
Standard InCHI:	InChI=1S/C31H50O5/c1-19(9-8-13-26(2,3)36-7)20-12-14-28(5)21-10-11-22-29(6,25(34)35)23(32)17-24(33)31(22)18-30(21,31)16-15-27(20,28)4/h8,13,19-24,32-33H,9-12,14-18H2,1-7H3,(H,34,35)/b13-8+/t19-,20-,21+,22+,23+,24+,27-,28+,29+,30+,31-/m1/s1
SMILES:	C[C@H](C/C=C/C(C)(C)OC)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@@](C)([C@H](C[C@@H]([C@]54C[C@@]35CC[C@]12C)O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472834
PubChem CID:	10815332
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	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	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	=	86.1	ug ml-1	PMID[548978]

☑ 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 NPC263729 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	1348
0.2-0.3	4449
0.3-0.4	8917
0.4-0.5	12638
0.5-0.6	6311
0.6-0.7	6056
0.7-0.8	2608
0.8-0.85	131
0.85-0.9	21
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9596	High Similarity	NPC201763
0.9505	High Similarity	NPC163216
0.9412	High Similarity	NPC257082
0.9412	High Similarity	NPC285298
0.901	High Similarity	NPC193934
0.901	High Similarity	NPC271980
0.8922	High Similarity	NPC312900
0.8889	High Similarity	NPC160056
0.8812	High Similarity	NPC180733
0.8812	High Similarity	NPC37047
0.8812	High Similarity	NPC41971
0.8788	High Similarity	NPC288906
0.8788	High Similarity	NPC263135
0.8738	High Similarity	NPC222153
0.8716	High Similarity	NPC72772
0.8716	High Similarity	NPC469794
0.8627	High Similarity	NPC94906
0.8571	High Similarity	NPC184555
0.8544	High Similarity	NPC477052
0.8544	High Similarity	NPC477051
0.8544	High Similarity	NPC75941
0.8544	High Similarity	NPC477053
0.8529	High Similarity	NPC477854
0.8529	High Similarity	NPC472028
0.8529	High Similarity	NPC119036
0.8515	High Similarity	NPC327788
0.8515	High Similarity	NPC234564
0.8505	High Similarity	NPC173905
0.8505	High Similarity	NPC5475
0.8505	High Similarity	NPC472216
0.8505	High Similarity	NPC284828
0.8462	Intermediate Similarity	NPC477054
0.8462	Intermediate Similarity	NPC124544
0.8416	Intermediate Similarity	NPC279974
0.8416	Intermediate Similarity	NPC84383
0.84	Intermediate Similarity	NPC477855
0.8381	Intermediate Similarity	NPC112009
0.8365	Intermediate Similarity	NPC71706
0.8349	Intermediate Similarity	NPC270586
0.8348	Intermediate Similarity	NPC55602
0.8348	Intermediate Similarity	NPC11895
0.8333	Intermediate Similarity	NPC477853
0.8319	Intermediate Similarity	NPC476960
0.8304	Intermediate Similarity	NPC476959
0.8288	Intermediate Similarity	NPC470953
0.8273	Intermediate Similarity	NPC90952
0.8273	Intermediate Similarity	NPC277769
0.8273	Intermediate Similarity	NPC4573
0.8269	Intermediate Similarity	NPC117685
0.8269	Intermediate Similarity	NPC477521
0.8261	Intermediate Similarity	NPC170538
0.8257	Intermediate Similarity	NPC472215
0.8257	Intermediate Similarity	NPC472214
0.8246	Intermediate Similarity	NPC476962
0.8241	Intermediate Similarity	NPC472218
0.8241	Intermediate Similarity	NPC472219
0.8241	Intermediate Similarity	NPC472217
0.8235	Intermediate Similarity	NPC266899
0.8235	Intermediate Similarity	NPC266431
0.8224	Intermediate Similarity	NPC295366
0.8214	Intermediate Similarity	NPC476963
0.8208	Intermediate Similarity	NPC36688
0.8208	Intermediate Similarity	NPC180204
0.8205	Intermediate Similarity	NPC293112
0.8198	Intermediate Similarity	NPC122056
0.819	Intermediate Similarity	NPC469789
0.819	Intermediate Similarity	NPC235142
0.819	Intermediate Similarity	NPC471412
0.8182	Intermediate Similarity	NPC146937
0.8163	Intermediate Similarity	NPC302111
0.8155	Intermediate Similarity	NPC114743
0.8155	Intermediate Similarity	NPC195366
0.8148	Intermediate Similarity	NPC329048
0.8148	Intermediate Similarity	NPC330011
0.8148	Intermediate Similarity	NPC131665
0.8148	Intermediate Similarity	NPC255387
0.8142	Intermediate Similarity	NPC239273
0.8142	Intermediate Similarity	NPC55296
0.8131	Intermediate Similarity	NPC29705
0.8131	Intermediate Similarity	NPC471293
0.8125	Intermediate Similarity	NPC238667
0.812	Intermediate Similarity	NPC233041
0.812	Intermediate Similarity	NPC81736
0.812	Intermediate Similarity	NPC8369
0.812	Intermediate Similarity	NPC172154
0.8113	Intermediate Similarity	NPC476081
0.8113	Intermediate Similarity	NPC170615
0.8108	Intermediate Similarity	NPC476964
0.8108	Intermediate Similarity	NPC476163
0.81	Intermediate Similarity	NPC56962
0.81	Intermediate Similarity	NPC128496
0.81	Intermediate Similarity	NPC24705
0.81	Intermediate Similarity	NPC474704
0.81	Intermediate Similarity	NPC475921
0.8095	Intermediate Similarity	NPC470074
0.8095	Intermediate Similarity	NPC201406
0.8095	Intermediate Similarity	NPC251680
0.8095	Intermediate Similarity	NPC471413
0.8087	Intermediate Similarity	NPC268530
0.8087	Intermediate Similarity	NPC154491
0.8087	Intermediate Similarity	NPC476961
0.8087	Intermediate Similarity	NPC251226
0.8077	Intermediate Similarity	NPC469810
0.8077	Intermediate Similarity	NPC253586
0.8077	Intermediate Similarity	NPC156546
0.807	Intermediate Similarity	NPC146786
0.8053	Intermediate Similarity	NPC196931
0.8053	Intermediate Similarity	NPC270929
0.8051	Intermediate Similarity	NPC473635
0.8037	Intermediate Similarity	NPC10232
0.8037	Intermediate Similarity	NPC187302
0.8037	Intermediate Similarity	NPC476237
0.8037	Intermediate Similarity	NPC329345
0.8037	Intermediate Similarity	NPC189588
0.8037	Intermediate Similarity	NPC297617
0.8037	Intermediate Similarity	NPC196471
0.8037	Intermediate Similarity	NPC473283
0.8037	Intermediate Similarity	NPC475526
0.8037	Intermediate Similarity	NPC97487
0.8037	Intermediate Similarity	NPC120321
0.8036	Intermediate Similarity	NPC312017
0.8036	Intermediate Similarity	NPC73050
0.8036	Intermediate Similarity	NPC9848
0.8034	Intermediate Similarity	NPC204812
0.8019	Intermediate Similarity	NPC46848
0.8019	Intermediate Similarity	NPC282524
0.8019	Intermediate Similarity	NPC289670
0.8019	Intermediate Similarity	NPC472924
0.8017	Intermediate Similarity	NPC4021
0.8017	Intermediate Similarity	NPC159456
0.8017	Intermediate Similarity	NPC67569
0.8	Intermediate Similarity	NPC42673
0.8	Intermediate Similarity	NPC231529
0.8	Intermediate Similarity	NPC124703
0.8	Intermediate Similarity	NPC191565
0.8	Intermediate Similarity	NPC98868
0.8	Intermediate Similarity	NPC218107
0.8	Intermediate Similarity	NPC230513
0.8	Intermediate Similarity	NPC234617
0.8	Intermediate Similarity	NPC114274
0.8	Intermediate Similarity	NPC57079
0.8	Intermediate Similarity	NPC475065
0.8	Intermediate Similarity	NPC108368
0.8	Intermediate Similarity	NPC193360
0.7983	Intermediate Similarity	NPC117702
0.7983	Intermediate Similarity	NPC469757
0.7983	Intermediate Similarity	NPC146456
0.7983	Intermediate Similarity	NPC471357
0.7982	Intermediate Similarity	NPC167606
0.7982	Intermediate Similarity	NPC475809
0.7982	Intermediate Similarity	NPC134430
0.7982	Intermediate Similarity	NPC472925
0.7982	Intermediate Similarity	NPC140055
0.7982	Intermediate Similarity	NPC470952
0.7982	Intermediate Similarity	NPC286528
0.7982	Intermediate Similarity	NPC476965
0.7982	Intermediate Similarity	NPC469684
0.7982	Intermediate Similarity	NPC20302
0.7982	Intermediate Similarity	NPC64844
0.7982	Intermediate Similarity	NPC59530
0.7982	Intermediate Similarity	NPC42847
0.7982	Intermediate Similarity	NPC474518
0.7982	Intermediate Similarity	NPC470959
0.7982	Intermediate Similarity	NPC475294
0.7981	Intermediate Similarity	NPC471153
0.7981	Intermediate Similarity	NPC173272
0.7981	Intermediate Similarity	NPC329910
0.7981	Intermediate Similarity	NPC471903
0.7981	Intermediate Similarity	NPC29152
0.7966	Intermediate Similarity	NPC241456
0.7966	Intermediate Similarity	NPC32868
0.7965	Intermediate Similarity	NPC147912
0.7965	Intermediate Similarity	NPC284915
0.7965	Intermediate Similarity	NPC67259
0.7963	Intermediate Similarity	NPC72255
0.7963	Intermediate Similarity	NPC475036
0.7963	Intermediate Similarity	NPC474281
0.7961	Intermediate Similarity	NPC470385
0.7961	Intermediate Similarity	NPC470386
0.7961	Intermediate Similarity	NPC91010
0.7961	Intermediate Similarity	NPC209662
0.7949	Intermediate Similarity	NPC470265
0.7949	Intermediate Similarity	NPC23786
0.7946	Intermediate Similarity	NPC470063
0.7944	Intermediate Similarity	NPC475558
0.7944	Intermediate Similarity	NPC304832
0.7944	Intermediate Similarity	NPC473788
0.7944	Intermediate Similarity	NPC185530
0.7944	Intermediate Similarity	NPC88203
0.7944	Intermediate Similarity	NPC76866
0.7944	Intermediate Similarity	NPC148628
0.7944	Intermediate Similarity	NPC162973
0.7944	Intermediate Similarity	NPC155332
0.7944	Intermediate Similarity	NPC32577
0.7944	Intermediate Similarity	NPC114540
0.7944	Intermediate Similarity	NPC275990
0.7944	Intermediate Similarity	NPC246736
0.7944	Intermediate Similarity	NPC214946
0.7944	Intermediate Similarity	NPC286519
0.7941	Intermediate Similarity	NPC211403

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 NPC263729 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1566
0.2-0.3	3850
0.3-0.4	2320
0.4-0.5	728
0.5-0.6	213
0.6-0.7	211
0.7-0.8	81
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8173	Intermediate Similarity	NPD7638	Approved
0.8095	Intermediate Similarity	NPD7640	Approved
0.8095	Intermediate Similarity	NPD7639	Approved
0.7982	Intermediate Similarity	NPD7115	Discovery
0.7851	Intermediate Similarity	NPD7319	Approved
0.7748	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6881	Approved
0.7748	Intermediate Similarity	NPD6899	Approved
0.7727	Intermediate Similarity	NPD6675	Approved
0.7727	Intermediate Similarity	NPD7128	Approved
0.7727	Intermediate Similarity	NPD6402	Approved
0.7727	Intermediate Similarity	NPD5739	Approved
0.7658	Intermediate Similarity	NPD5697	Approved
0.7611	Intermediate Similarity	NPD6883	Approved
0.7611	Intermediate Similarity	NPD7290	Approved
0.7611	Intermediate Similarity	NPD7102	Approved
0.7603	Intermediate Similarity	NPD7507	Approved
0.7596	Intermediate Similarity	NPD6079	Approved
0.7596	Intermediate Similarity	NPD7637	Suspended
0.7589	Intermediate Similarity	NPD7320	Approved
0.7573	Intermediate Similarity	NPD5328	Approved
0.7544	Intermediate Similarity	NPD6617	Approved
0.7544	Intermediate Similarity	NPD6650	Approved
0.7544	Intermediate Similarity	NPD6869	Approved
0.7544	Intermediate Similarity	NPD6649	Approved
0.7544	Intermediate Similarity	NPD6847	Approved
0.7544	Intermediate Similarity	NPD8130	Phase 1
0.7525	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6372	Approved
0.7522	Intermediate Similarity	NPD6373	Approved
0.7522	Intermediate Similarity	NPD6013	Approved
0.7522	Intermediate Similarity	NPD6014	Approved
0.7522	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD5701	Approved
0.7479	Intermediate Similarity	NPD6319	Approved
0.7478	Intermediate Similarity	NPD6882	Approved
0.7478	Intermediate Similarity	NPD8297	Approved
0.7456	Intermediate Similarity	NPD4634	Approved
0.7455	Intermediate Similarity	NPD7632	Discontinued
0.7455	Intermediate Similarity	NPD5211	Phase 2
0.7434	Intermediate Similarity	NPD6011	Approved
0.7431	Intermediate Similarity	NPD5285	Approved
0.7431	Intermediate Similarity	NPD5286	Approved
0.7431	Intermediate Similarity	NPD4696	Approved
0.7414	Intermediate Similarity	NPD4632	Approved
0.7407	Intermediate Similarity	NPD4755	Approved
0.7377	Intermediate Similarity	NPD7492	Approved
0.7368	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6399	Phase 3
0.7358	Intermediate Similarity	NPD5778	Approved
0.7358	Intermediate Similarity	NPD5779	Approved
0.7347	Intermediate Similarity	NPD6697	Approved
0.7347	Intermediate Similarity	NPD6118	Approved
0.7347	Intermediate Similarity	NPD6114	Approved
0.7347	Intermediate Similarity	NPD6115	Approved
0.7339	Intermediate Similarity	NPD7736	Approved
0.7333	Intermediate Similarity	NPD6054	Approved
0.7321	Intermediate Similarity	NPD5141	Approved
0.7317	Intermediate Similarity	NPD6616	Approved
0.7315	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5221	Approved
0.7315	Intermediate Similarity	NPD5222	Approved
0.7297	Intermediate Similarity	NPD5225	Approved
0.7297	Intermediate Similarity	NPD5224	Approved
0.7297	Intermediate Similarity	NPD5226	Approved
0.7297	Intermediate Similarity	NPD4633	Approved
0.7295	Intermediate Similarity	NPD7604	Phase 2
0.7273	Intermediate Similarity	NPD4700	Approved
0.7264	Intermediate Similarity	NPD8034	Phase 2
0.7264	Intermediate Similarity	NPD6411	Approved
0.7264	Intermediate Similarity	NPD8035	Phase 2
0.7264	Intermediate Similarity	NPD7515	Phase 2
0.7258	Intermediate Similarity	NPD7078	Approved
0.7257	Intermediate Similarity	NPD6008	Approved
0.7255	Intermediate Similarity	NPD4786	Approved
0.7248	Intermediate Similarity	NPD6084	Phase 2
0.7248	Intermediate Similarity	NPD5173	Approved
0.7248	Intermediate Similarity	NPD6083	Phase 2
0.7241	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5174	Approved
0.7232	Intermediate Similarity	NPD5175	Approved
0.7227	Intermediate Similarity	NPD6009	Approved
0.7213	Intermediate Similarity	NPD6370	Approved
0.7207	Intermediate Similarity	NPD5223	Approved
0.72	Intermediate Similarity	NPD7525	Registered
0.719	Intermediate Similarity	NPD6059	Approved
0.7182	Intermediate Similarity	NPD4225	Approved
0.7179	Intermediate Similarity	NPD6053	Discontinued
0.7167	Intermediate Similarity	NPD7327	Approved
0.7167	Intermediate Similarity	NPD7328	Approved
0.7156	Intermediate Similarity	NPD4697	Phase 3
0.7155	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6117	Approved
0.7131	Intermediate Similarity	NPD6016	Approved
0.7131	Intermediate Similarity	NPD6015	Approved
0.713	Intermediate Similarity	NPD7748	Approved
0.712	Intermediate Similarity	NPD8293	Discontinued
0.7115	Intermediate Similarity	NPD3618	Phase 1
0.7107	Intermediate Similarity	NPD7516	Approved
0.7107	Intermediate Similarity	NPD7101	Approved
0.7107	Intermediate Similarity	NPD7100	Approved
0.7075	Intermediate Similarity	NPD6101	Approved
0.7075	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5988	Approved
0.7071	Intermediate Similarity	NPD6116	Phase 1
0.7064	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3667	Approved
0.7037	Intermediate Similarity	NPD4202	Approved
0.7025	Intermediate Similarity	NPD6335	Approved
0.7009	Intermediate Similarity	NPD5785	Approved
0.7	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6274	Approved
0.7	Intermediate Similarity	NPD6868	Approved
0.6992	Remote Similarity	NPD8380	Approved
0.6992	Remote Similarity	NPD8296	Approved
0.6992	Remote Similarity	NPD5983	Phase 2
0.6992	Remote Similarity	NPD8379	Approved
0.6992	Remote Similarity	NPD8335	Approved
0.6992	Remote Similarity	NPD8378	Approved
0.6992	Remote Similarity	NPD6921	Approved
0.6983	Remote Similarity	NPD4730	Approved
0.6983	Remote Similarity	NPD4729	Approved
0.6983	Remote Similarity	NPD6686	Approved
0.6975	Remote Similarity	NPD8133	Approved
0.6957	Remote Similarity	NPD4767	Approved
0.6957	Remote Similarity	NPD4768	Approved
0.6952	Remote Similarity	NPD5786	Approved
0.6942	Remote Similarity	NPD6317	Approved
0.6939	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7902	Approved
0.693	Remote Similarity	NPD4754	Approved
0.6916	Remote Similarity	NPD6051	Approved
0.6916	Remote Similarity	NPD4753	Phase 2
0.6911	Remote Similarity	NPD8377	Approved
0.6911	Remote Similarity	NPD8294	Approved
0.6909	Remote Similarity	NPD5695	Phase 3
0.6905	Remote Similarity	NPD6336	Discontinued
0.6897	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6313	Approved
0.6885	Remote Similarity	NPD6314	Approved
0.6875	Remote Similarity	NPD5696	Approved
0.6869	Remote Similarity	NPD3703	Phase 2
0.6864	Remote Similarity	NPD5251	Approved
0.6864	Remote Similarity	NPD5250	Approved
0.6864	Remote Similarity	NPD5249	Phase 3
0.6864	Remote Similarity	NPD5248	Approved
0.6864	Remote Similarity	NPD5247	Approved
0.6855	Remote Similarity	NPD6908	Approved
0.6855	Remote Similarity	NPD8033	Approved
0.6855	Remote Similarity	NPD6909	Approved
0.6838	Remote Similarity	NPD5128	Approved
0.6827	Remote Similarity	NPD6695	Phase 3
0.6822	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5737	Approved
0.6822	Remote Similarity	NPD6672	Approved
0.6807	Remote Similarity	NPD5215	Approved
0.6807	Remote Similarity	NPD5216	Approved
0.6807	Remote Similarity	NPD5217	Approved
0.6796	Remote Similarity	NPD5369	Approved
0.6796	Remote Similarity	NPD6902	Approved
0.6792	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7334	Approved
0.6792	Remote Similarity	NPD7146	Approved
0.6792	Remote Similarity	NPD6684	Approved
0.6792	Remote Similarity	NPD5330	Approved
0.6792	Remote Similarity	NPD7521	Approved
0.6792	Remote Similarity	NPD6409	Approved
0.6789	Remote Similarity	NPD5693	Phase 1
0.6762	Remote Similarity	NPD3665	Phase 1
0.6762	Remote Similarity	NPD3666	Approved
0.6762	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD3133	Approved
0.6757	Remote Similarity	NPD5210	Approved
0.6757	Remote Similarity	NPD4629	Approved
0.6746	Remote Similarity	NPD8328	Phase 3
0.6731	Remote Similarity	NPD4270	Approved
0.6731	Remote Similarity	NPD6435	Approved
0.6731	Remote Similarity	NPD4269	Approved
0.6731	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD3573	Approved
0.6723	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5135	Approved
0.6723	Remote Similarity	NPD5169	Approved
0.6723	Remote Similarity	NPD6371	Approved
0.672	Remote Similarity	NPD8516	Approved
0.672	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7503	Approved
0.672	Remote Similarity	NPD8513	Phase 3
0.672	Remote Similarity	NPD8515	Approved
0.672	Remote Similarity	NPD8517	Approved
0.6699	Remote Similarity	NPD6931	Approved
0.6699	Remote Similarity	NPD5368	Approved
0.6699	Remote Similarity	NPD6930	Phase 2
0.6699	Remote Similarity	NPD7514	Phase 3
0.6695	Remote Similarity	NPD5168	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD5362	Discontinued

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