NPASS Compound

Structure

NPC6326 OpenBabel07101719252D 42 46 0 0 1 0 0 0 0 0999 V2000 0.9176 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3668 -1.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4969 -4.2581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1348 -2.0101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6348 -1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6158 -0.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1349 -0.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7864 -4.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6245 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6245 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0543 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0543 -0.1388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4623 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1245 0.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6213 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0824 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3668 -0.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2322 -3.2938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3155 0.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0543 -1.4792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6348 -0.4739 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4739 -0.4739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9204 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2054 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3644 0.3601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6348 -1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6213 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4739 -1.1441 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6702 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6702 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2328 0.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7353 -3.0409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7864 -2.4792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9975 2.6254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3827 -2.5419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9204 -3.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9335 0.0511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5008 0.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1565 1.3383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9350 -2.5824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 8 37 1 0 0 0 0 9 10 2 0 0 0 0 9 19 1 0 0 0 0 10 38 1 0 0 0 0 11 20 1 0 0 0 0 11 23 1 0 0 0 0 12 21 1 0 0 0 0 12 22 1 0 0 0 0 13 24 1 0 0 0 0 14 19 2 0 0 0 0 14 38 1 0 0 0 0 15 28 1 0 0 0 0 15 30 1 0 0 0 0 16 30 1 0 0 0 0 16 31 1 0 0 0 0 17 32 2 0 0 0 0 17 39 1 0 0 0 0 18 33 2 0 0 0 0 18 41 1 0 0 0 0 19 25 1 0 0 0 0 20 27 1 0 0 0 0 20 29 1 6 0 0 0 21 27 1 0 0 0 0 21 39 1 1 0 0 0 22 29 1 1 0 0 0 22 42 1 0 0 0 0 23 34 2 0 0 0 0 23 37 1 0 0 0 0 24 35 2 0 0 0 0 24 40 1 0 0 0 0 25 28 1 6 0 0 0 25 40 1 0 0 0 0 26 29 1 0 0 0 0 26 30 1 0 0 0 0 26 36 2 0 0 0 0 28 31 1 6 0 0 0 29 7 1 6 0 0 0 30 41 1 6 0 0 0 31 13 1 6 0 0 0 31 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.24
Volume:	577.551
LogP:	3.187
LogD:	1.782
LogS:	-4.741
# Rotatable Bonds:	8
TPSA:	144.64
# H-Bond Aceptor:	11
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.282
Synthetic Accessibility Score:	6.484
Fsp3:	0.645
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:	-5.273
MDCK Permeability:	6.029053110978566e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.204
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.867
Plasma Protein Binding (PPB):	68.88374328613281%
Volume Distribution (VD):	1.263
Pgp-substrate:	34.74995422363281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.123
CYP2C19-substrate:	0.329
CYP2C9-inhibitor:	0.436
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.906
CYP3A4-substrate:	0.905

ADMET: Excretion

Clearance (CL):	2.779
Half-life (T1/2):	0.438

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.664
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.431
Rat Oral Acute Toxicity:	0.974
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.199
Carcinogencity:	0.614
Eye Corrosion:	0.852
Eye Irritation:	0.097
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC6326

Natural Product ID:	NPC6326
*Common Name:**	Cipatrijugin C
IUPAC Name:	n.a.
Synonyms:	Cipatrijugin C
Standard InCHIKey:	VBUVTRXWAVCMCB-YAVIGIRXSA-N
Standard InCHI:	InChI=1S/C31H38O11/c1-16-30(41-18(3)33)15-28(6)25(19-9-10-38-14-19)40-24(35)13-31(16,28)42-22-12-21(39-17(2)32)27(4,5)20(11-23(34)37-8)29(22,7)26(30)36/h9-10,14,20-22,25H,1,11-13,15H2,2-8H3/t20-,21+,22-,25-,28-,29+,30+,31-/m0/s1
SMILES:	C=C1[C@@]2(C[C@@]3(C)[C@H](c4ccoc4)OC(=O)C[C@]13O[C@H]1C[C@H](C(C)(C)[C@H](CC(=O)OC)[C@@]1(C)C2=O)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252939
PubChem CID:	23626012
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids 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
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17655260]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[19296669]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	Longlin County of Guangxi Province, China	2012-JUL	PMID[25970729]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[476200]
NPT111	Cell Line	K562	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[476200]

☑ 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 NPC6326 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	440
0.1-0.2	1624
0.2-0.3	3499
0.3-0.4	6811
0.4-0.5	11892
0.5-0.6	9339
0.6-0.7	7928
0.7-0.8	887
0.8-0.85	225
0.85-0.9	40
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9801	High Similarity	NPC195131
0.9742	High Similarity	NPC476224
0.9735	High Similarity	NPC204663
0.9677	High Similarity	NPC149945
0.9484	High Similarity	NPC472767
0.9367	High Similarity	NPC472764
0.9308	High Similarity	NPC472766
0.9308	High Similarity	NPC472765
0.9114	High Similarity	NPC197596
0.9068	High Similarity	NPC327922
0.9062	High Similarity	NPC478178
0.9057	High Similarity	NPC165218
0.9026	High Similarity	NPC156189
0.8987	High Similarity	NPC237155
0.897	High Similarity	NPC478177
0.8963	High Similarity	NPC236004
0.8938	High Similarity	NPC472669
0.8924	High Similarity	NPC472772
0.8924	High Similarity	NPC167142
0.8902	High Similarity	NPC469848
0.8889	High Similarity	NPC478179
0.8875	High Similarity	NPC470939
0.8875	High Similarity	NPC471166
0.8875	High Similarity	NPC471167
0.8875	High Similarity	NPC472668
0.8848	High Similarity	NPC471437
0.8848	High Similarity	NPC471632
0.8848	High Similarity	NPC94763
0.8841	High Similarity	NPC285227
0.8839	High Similarity	NPC470790
0.8839	High Similarity	NPC470791
0.8831	High Similarity	NPC470941
0.8827	High Similarity	NPC214600
0.882	High Similarity	NPC224394
0.882	High Similarity	NPC663
0.882	High Similarity	NPC471168
0.8812	High Similarity	NPC191828
0.8805	High Similarity	NPC472283
0.8782	High Similarity	NPC196864
0.8782	High Similarity	NPC477404
0.8782	High Similarity	NPC469335
0.8782	High Similarity	NPC159927
0.878	High Similarity	NPC472659
0.8773	High Similarity	NPC476853
0.8773	High Similarity	NPC472775
0.8773	High Similarity	NPC472774
0.8766	High Similarity	NPC262198
0.8758	High Similarity	NPC472771
0.875	High Similarity	NPC474932
0.875	High Similarity	NPC477403
0.8742	High Similarity	NPC126723
0.8742	High Similarity	NPC263265
0.8727	High Similarity	NPC159232
0.8718	High Similarity	NPC329180
0.8704	High Similarity	NPC472773
0.8696	High Similarity	NPC25255
0.8696	High Similarity	NPC305016
0.8688	High Similarity	NPC286722
0.8688	High Similarity	NPC249021
0.8679	High Similarity	NPC469850
0.8662	High Similarity	NPC476122
0.8659	High Similarity	NPC476850
0.8659	High Similarity	NPC476861
0.865	High Similarity	NPC476856
0.865	High Similarity	NPC123088
0.865	High Similarity	NPC476858
0.865	High Similarity	NPC476857
0.865	High Similarity	NPC476860
0.8642	High Similarity	NPC193798
0.8634	High Similarity	NPC473473
0.8634	High Similarity	NPC475295
0.8625	High Similarity	NPC60973
0.8625	High Similarity	NPC209364
0.8625	High Similarity	NPC107646
0.8623	High Similarity	NPC469576
0.8598	High Similarity	NPC23387
0.859	High Similarity	NPC221809
0.8589	High Similarity	NPC469846
0.8589	High Similarity	NPC469338
0.8589	High Similarity	NPC477405
0.8589	High Similarity	NPC292389
0.858	High Similarity	NPC477402
0.858	High Similarity	NPC470789
0.858	High Similarity	NPC475381
0.8571	High Similarity	NPC45101
0.8571	High Similarity	NPC469633
0.8571	High Similarity	NPC167340
0.8562	High Similarity	NPC469336
0.8562	High Similarity	NPC264943
0.8562	High Similarity	NPC471175
0.8553	High Similarity	NPC476201
0.8545	High Similarity	NPC173516
0.8545	High Similarity	NPC472651
0.8545	High Similarity	NPC473753
0.8545	High Similarity	NPC473766
0.8537	High Similarity	NPC469849
0.8537	High Similarity	NPC276551
0.8537	High Similarity	NPC470940
0.8529	High Similarity	NPC470938
0.8528	High Similarity	NPC69028
0.8528	High Similarity	NPC329938
0.8528	High Similarity	NPC82851
0.8521	High Similarity	NPC470181
0.8509	High Similarity	NPC175964
0.8509	High Similarity	NPC471169
0.85	High Similarity	NPC282445
0.85	High Similarity	NPC178932
0.8494	Intermediate Similarity	NPC160651
0.8494	Intermediate Similarity	NPC472652
0.8494	Intermediate Similarity	NPC471397
0.8491	Intermediate Similarity	NPC116717
0.8491	Intermediate Similarity	NPC18135
0.8488	Intermediate Similarity	NPC105395
0.8488	Intermediate Similarity	NPC247563
0.8488	Intermediate Similarity	NPC242068
0.8485	Intermediate Similarity	NPC470875
0.8481	Intermediate Similarity	NPC472654
0.8476	Intermediate Similarity	NPC302369
0.8476	Intermediate Similarity	NPC134254
0.8476	Intermediate Similarity	NPC39986
0.8476	Intermediate Similarity	NPC476197
0.8466	Intermediate Similarity	NPC472653
0.8457	Intermediate Similarity	NPC36655
0.8457	Intermediate Similarity	NPC261597
0.8452	Intermediate Similarity	NPC223415
0.8447	Intermediate Similarity	NPC44675
0.8447	Intermediate Similarity	NPC476262
0.8447	Intermediate Similarity	NPC214541
0.8438	Intermediate Similarity	NPC29695
0.8438	Intermediate Similarity	NPC469503
0.8438	Intermediate Similarity	NPC84063
0.8438	Intermediate Similarity	NPC182427
0.8438	Intermediate Similarity	NPC75906
0.8434	Intermediate Similarity	NPC472282
0.8428	Intermediate Similarity	NPC46551
0.8415	Intermediate Similarity	NPC263432
0.8415	Intermediate Similarity	NPC5079
0.8405	Intermediate Similarity	NPC475967
0.8405	Intermediate Similarity	NPC472779
0.8397	Intermediate Similarity	NPC86935
0.8395	Intermediate Similarity	NPC469485
0.8383	Intermediate Similarity	NPC271235
0.8383	Intermediate Similarity	NPC242334
0.8375	Intermediate Similarity	NPC272590
0.8364	Intermediate Similarity	NPC51568
0.8364	Intermediate Similarity	NPC419
0.8364	Intermediate Similarity	NPC234660
0.8354	Intermediate Similarity	NPC335761
0.8344	Intermediate Similarity	NPC173544
0.8344	Intermediate Similarity	NPC469847
0.8344	Intermediate Similarity	NPC187149
0.8333	Intermediate Similarity	NPC470995
0.8333	Intermediate Similarity	NPC75310
0.8323	Intermediate Similarity	NPC20500
0.8313	Intermediate Similarity	NPC261184
0.8303	Intermediate Similarity	NPC117986
0.8303	Intermediate Similarity	NPC5741
0.8294	Intermediate Similarity	NPC477824
0.8293	Intermediate Similarity	NPC475226
0.8291	Intermediate Similarity	NPC471292
0.8284	Intermediate Similarity	NPC160818
0.8284	Intermediate Similarity	NPC169299
0.828	Intermediate Similarity	NPC238843
0.828	Intermediate Similarity	NPC199044
0.828	Intermediate Similarity	NPC142113
0.8272	Intermediate Similarity	NPC57998
0.8261	Intermediate Similarity	NPC240214
0.8261	Intermediate Similarity	NPC291150
0.825	Intermediate Similarity	NPC195325
0.8247	Intermediate Similarity	NPC476943
0.8242	Intermediate Similarity	NPC333139
0.8232	Intermediate Similarity	NPC472778
0.8232	Intermediate Similarity	NPC299038
0.8232	Intermediate Similarity	NPC472777
0.8232	Intermediate Similarity	NPC197137
0.8232	Intermediate Similarity	NPC472776
0.8232	Intermediate Similarity	NPC470118
0.8232	Intermediate Similarity	NPC475066
0.8228	Intermediate Similarity	NPC34056
0.8225	Intermediate Similarity	NPC472650
0.8221	Intermediate Similarity	NPC92979
0.8217	Intermediate Similarity	NPC80635
0.8217	Intermediate Similarity	NPC243577
0.8217	Intermediate Similarity	NPC470741
0.8212	Intermediate Similarity	NPC471817
0.821	Intermediate Similarity	NPC322546
0.821	Intermediate Similarity	NPC308205
0.821	Intermediate Similarity	NPC246164
0.821	Intermediate Similarity	NPC475777
0.8204	Intermediate Similarity	NPC271657
0.8204	Intermediate Similarity	NPC259943
0.8199	Intermediate Similarity	NPC5180
0.8193	Intermediate Similarity	NPC18347
0.8193	Intermediate Similarity	NPC149896
0.8193	Intermediate Similarity	NPC96443
0.8193	Intermediate Similarity	NPC290400
0.8193	Intermediate Similarity	NPC200782
0.8187	Intermediate Similarity	NPC19747
0.8182	Intermediate Similarity	NPC473368
0.8182	Intermediate Similarity	NPC310830

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 NPC6326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	1072
0.2-0.3	2355
0.3-0.4	2763
0.4-0.5	1752
0.5-0.6	645
0.6-0.7	190
0.7-0.8	8
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8562	High Similarity	NPD5760	Phase 2
0.8562	High Similarity	NPD5761	Phase 2
0.8242	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6764	Approved
0.7727	Intermediate Similarity	NPD6765	Approved
0.7709	Intermediate Similarity	NPD8434	Phase 2
0.7556	Intermediate Similarity	NPD6784	Approved
0.7556	Intermediate Similarity	NPD6785	Approved
0.7321	Intermediate Similarity	NPD920	Approved
0.7216	Intermediate Similarity	NPD1247	Approved
0.7202	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD919	Approved
0.7195	Intermediate Similarity	NPD1471	Phase 3
0.7168	Intermediate Similarity	NPD7819	Suspended
0.7168	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7075	Discontinued
0.7093	Intermediate Similarity	NPD6599	Discontinued
0.7083	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7236	Approved
0.6966	Remote Similarity	NPD5494	Approved
0.6954	Remote Similarity	NPD7411	Suspended
0.6941	Remote Similarity	NPD6799	Approved
0.6932	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7799	Discontinued
0.6914	Remote Similarity	NPD6801	Discontinued
0.6905	Remote Similarity	NPD1243	Approved
0.6879	Remote Similarity	NPD7239	Suspended
0.6854	Remote Similarity	NPD3749	Approved
0.6836	Remote Similarity	NPD3817	Phase 2
0.6831	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2796	Approved
0.6786	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6002	Phase 3
0.6786	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6005	Phase 3
0.6786	Remote Similarity	NPD6004	Phase 3
0.6774	Remote Similarity	NPD6559	Discontinued
0.6766	Remote Similarity	NPD2799	Discontinued
0.6763	Remote Similarity	NPD6273	Approved
0.6758	Remote Similarity	NPD3926	Phase 2
0.6743	Remote Similarity	NPD3226	Approved
0.6742	Remote Similarity	NPD5402	Approved
0.6721	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2534	Approved
0.6705	Remote Similarity	NPD2532	Approved
0.6705	Remote Similarity	NPD2533	Approved
0.6705	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD3882	Suspended
0.6687	Remote Similarity	NPD6832	Phase 2
0.6667	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8404	Phase 2
0.663	Remote Similarity	NPD2403	Approved
0.6629	Remote Similarity	NPD5403	Approved
0.6613	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6808	Phase 2
0.6609	Remote Similarity	NPD5401	Approved
0.6609	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2800	Approved
0.6596	Remote Similarity	NPD7685	Pre-registration
0.6592	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5762	Approved
0.6588	Remote Similarity	NPD5763	Approved
0.6568	Remote Similarity	NPD3748	Approved
0.6557	Remote Similarity	NPD8127	Discontinued
0.655	Remote Similarity	NPD1549	Phase 2
0.655	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7057	Phase 3
0.6519	Remote Similarity	NPD7058	Phase 2
0.6517	Remote Similarity	NPD4380	Phase 2
0.6505	Remote Similarity	NPD7473	Discontinued
0.6491	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD2346	Discontinued
0.6491	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6355	Discontinued
0.6484	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3818	Discontinued
0.6468	Remote Similarity	NPD7497	Discontinued
0.6467	Remote Similarity	NPD7199	Phase 2
0.6467	Remote Similarity	NPD8032	Phase 2
0.6467	Remote Similarity	NPD6959	Discontinued
0.6463	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6166	Phase 2
0.6452	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD1934	Approved
0.6441	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD3887	Approved
0.6436	Remote Similarity	NPD5844	Phase 1
0.6433	Remote Similarity	NPD1551	Phase 2
0.6433	Remote Similarity	NPD6099	Approved
0.6433	Remote Similarity	NPD6100	Approved
0.6429	Remote Similarity	NPD7768	Phase 2
0.6421	Remote Similarity	NPD7251	Discontinued
0.642	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD3266	Approved
0.6402	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD3267	Approved
0.64	Remote Similarity	NPD4107	Approved
0.6395	Remote Similarity	NPD2344	Approved
0.6391	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7808	Phase 3
0.6386	Remote Similarity	NPD7435	Discontinued
0.6383	Remote Similarity	NPD3751	Discontinued
0.6379	Remote Similarity	NPD3750	Approved
0.6379	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7033	Discontinued
0.6368	Remote Similarity	NPD6797	Phase 2
0.6354	Remote Similarity	NPD8313	Approved
0.6354	Remote Similarity	NPD8312	Approved
0.635	Remote Similarity	NPD8285	Discontinued
0.6344	Remote Similarity	NPD3787	Discontinued
0.6344	Remote Similarity	NPD7229	Phase 3
0.6344	Remote Similarity	NPD5710	Approved
0.6344	Remote Similarity	NPD5711	Approved
0.6344	Remote Similarity	NPD6232	Discontinued
0.6341	Remote Similarity	NPD1876	Approved
0.634	Remote Similarity	NPD8150	Discontinued
0.6337	Remote Similarity	NPD2935	Discontinued
0.6335	Remote Similarity	NPD17	Approved
0.6331	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8407	Phase 2
0.6316	Remote Similarity	NPD7074	Phase 3
0.631	Remote Similarity	NPD3268	Approved
0.631	Remote Similarity	NPD2313	Discontinued
0.6291	Remote Similarity	NPD7907	Approved
0.6287	Remote Similarity	NPD4482	Phase 3
0.6284	Remote Similarity	NPD5353	Approved
0.6283	Remote Similarity	NPD5953	Discontinued
0.6279	Remote Similarity	NPD1510	Phase 2
0.6278	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD1019	Discontinued
0.6265	Remote Similarity	NPD5647	Approved
0.6263	Remote Similarity	NPD7054	Approved
0.6263	Remote Similarity	NPD7286	Phase 2
0.6258	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD6651	Approved
0.6257	Remote Similarity	NPD6653	Approved
0.625	Remote Similarity	NPD4965	Approved
0.625	Remote Similarity	NPD8368	Discontinued
0.625	Remote Similarity	NPD4966	Approved
0.625	Remote Similarity	NPD2309	Approved
0.625	Remote Similarity	NPD4967	Phase 2
0.6235	Remote Similarity	NPD4140	Approved
0.6235	Remote Similarity	NPD1240	Approved
0.623	Remote Similarity	NPD7472	Approved
0.623	Remote Similarity	NPD2801	Approved
0.622	Remote Similarity	NPD3972	Approved
0.622	Remote Similarity	NPD1608	Approved
0.6209	Remote Similarity	NPD5890	Approved
0.6209	Remote Similarity	NPD5889	Approved
0.6207	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD2353	Approved
0.6205	Remote Similarity	NPD6362	Approved
0.6202	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD7874	Approved
0.6201	Remote Similarity	NPD1512	Approved
0.6201	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD7458	Discontinued
0.6183	Remote Similarity	NPD6234	Discontinued
0.6182	Remote Similarity	NPD5327	Phase 3
0.6175	Remote Similarity	NPD37	Approved
0.6175	Remote Similarity	NPD6279	Approved
0.6175	Remote Similarity	NPD6280	Approved
0.617	Remote Similarity	NPD7315	Approved
0.6163	Remote Similarity	NPD1607	Approved
0.6158	Remote Similarity	NPD6779	Approved
0.6158	Remote Similarity	NPD6777	Approved
0.6158	Remote Similarity	NPD6778	Approved
0.6158	Remote Similarity	NPD6776	Approved
0.6158	Remote Similarity	NPD6780	Approved
0.6158	Remote Similarity	NPD6781	Approved
0.6158	Remote Similarity	NPD6782	Approved
0.6157	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6585	Discontinued
0.6154	Remote Similarity	NPD7028	Phase 2
0.6146	Remote Similarity	NPD7696	Phase 3
0.6146	Remote Similarity	NPD7698	Approved
0.6146	Remote Similarity	NPD7697	Approved
0.6141	Remote Similarity	NPD1465	Phase 2
0.614	Remote Similarity	NPD4307	Phase 2
0.6126	Remote Similarity	NPD2163	Approved
0.6126	Remote Similarity	NPD7228	Approved
0.6121	Remote Similarity	NPD9717	Approved
0.6121	Remote Similarity	NPD4111	Phase 1
0.6121	Remote Similarity	NPD4665	Approved
0.612	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD3764	Approved
0.6118	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7871	Phase 2

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