NPASS Compound

Structure

CID14390 OpenBabel06191715342D 39 45 0 0 1 0 0 0 0 0999 V2000 -4.1217 2.5407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7757 -3.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3515 -0.4941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7782 4.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8139 4.1067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2633 3.2766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8919 4.9799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3346 3.2698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7841 2.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2925 4.0782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6264 0.2620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2635 1.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5792 0.4715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2163 2.1217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9106 4.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5244 -1.4584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8541 -1.4584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8197 2.4363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9686 0.9823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8741 1.4014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6892 -1.9406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5244 -0.4941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8541 -0.4941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5587 3.4186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8489 2.4334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0137 1.9512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6892 -0.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7029 1.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 3.4201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6961 0.9636 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0069 0.9755 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5578 2.4320 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7046 3.9127 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0634 3.9483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6961 0.9566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8268 1.6109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6892 -2.9955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4379 0.0334 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 36 1 0 0 0 0 2 37 1 0 0 0 0 3 38 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 18 2 0 0 0 0 9 18 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 19 2 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 14 20 1 0 0 0 0 15 33 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 17 23 2 0 0 0 0 18 26 1 0 0 0 0 20 36 1 0 0 0 0 21 37 1 0 0 0 0 22 27 2 0 0 0 0 22 38 1 0 0 0 0 23 27 1 0 0 0 0 23 39 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 25 28 2 0 0 0 0 25 29 1 0 0 0 0 26 31 1 6 0 0 0 27 30 1 0 0 0 0 28 30 1 0 0 0 0 28 32 1 0 0 0 0 29 33 1 0 0 0 0 29 34 2 0 0 0 0 30 31 1 6 0 0 0 30 35 1 0 0 0 0 31 19 1 6 0 0 0 31 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.19
Volume:	527.934
LogP:	4.104
LogD:	3.579
LogS:	-4.762
# Rotatable Bonds:	5
TPSA:	92.04
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	4.03
Fsp3:	0.29
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:	-5.286
MDCK Permeability:	2.015263271459844e-05
Pgp-inhibitor:	0.903
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.066
30% Bioavailability (F30%):	0.794

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	89.5152816772461%
Volume Distribution (VD):	0.474
Pgp-substrate:	3.5550241470336914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.688
CYP2C19-inhibitor:	0.815
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.937
CYP2C9-substrate:	0.449
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.554
CYP3A4-inhibitor:	0.972
CYP3A4-substrate:	0.934

ADMET: Excretion

Clearance (CL):	6.413
Half-life (T1/2):	0.362

ADMET: Toxicity

hERG Blockers:	0.806
Human Hepatotoxicity (H-HT):	0.826
Drug-inuced Liver Injury (DILI):	0.53
AMES Toxicity:	0.916
Rat Oral Acute Toxicity:	0.551
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.045
Carcinogencity:	0.351
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.747

Download Data

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

Natural Product: NPC14390

Natural Product ID:	NPC14390
*Common Name:**	YCIPQJTZJGUXND-JZRGNDHQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YCIPQJTZJGUXND-JZRGNDHQSA-N
Standard InCHI:	InChI=1S/C31H28N2O6/c1-36-20-13-11-19(12-14-20)31-26(18-8-5-4-6-9-18)25-28(32-24-10-7-15-33(24)29(25)34)30(31,35)27-22(38-3)16-21(37-2)17-23(27)39-31/h4-6,8-9,11-14,16-17,26,35H,7,10,15H2,1-3H3/t26-,30+,31+/m1/s1
SMILES:	COc1ccc(cc1)[C@]12Oc3c([C@]2(O)c2c([C@H]1c1ccccc1)c(=O)n1c(n2)CCC1)c(OC)cc(c3)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466993
PubChem CID:	5320808
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94986-0]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	flower	n.a.	PMID[17679444]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759160]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27686	Aglaia odorata	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
IC50	6

Activity Type	# Activity
Cell Line	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1294	Cell Line	NRK	Rattus norvegicus	IC50	=	0.081	ug.mL-1	PMID[570951]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	=	0.0089	ug.mL-1	PMID[570951]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	=	0.0078	ug.mL-1	PMID[570951]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	=	0.008	ug.mL-1	PMID[570951]
NPT1294	Cell Line	NRK	Rattus norvegicus	IC50	=	0.0098	ug.mL-1	PMID[570951]
NPT27	Others	Unspecified		IC50	=	0.0076	ug.mL-1	PMID[570951]

☑ 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 NPC14390 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	575
0.1-0.2	2444
0.2-0.3	11700
0.3-0.4	6830
0.4-0.5	13145
0.5-0.6	7274
0.6-0.7	693
0.7-0.8	35
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.898	High Similarity	NPC197125
0.8186	Intermediate Similarity	NPC293347
0.8177	Intermediate Similarity	NPC79130
0.804	Intermediate Similarity	NPC308709
0.7949	Intermediate Similarity	NPC206061
0.786	Intermediate Similarity	NPC475292
0.786	Intermediate Similarity	NPC475565
0.786	Intermediate Similarity	NPC475349
0.7824	Intermediate Similarity	NPC475624
0.7814	Intermediate Similarity	NPC470846
0.7778	Intermediate Similarity	NPC475442
0.7512	Intermediate Similarity	NPC235698
0.7476	Intermediate Similarity	NPC169605
0.7406	Intermediate Similarity	NPC258128
0.7379	Intermediate Similarity	NPC471563
0.7321	Intermediate Similarity	NPC470847
0.7308	Intermediate Similarity	NPC281629
0.7286	Intermediate Similarity	NPC476661
0.7268	Intermediate Similarity	NPC29531
0.7251	Intermediate Similarity	NPC476662
0.7243	Intermediate Similarity	NPC16249
0.7204	Intermediate Similarity	NPC471031
0.7204	Intermediate Similarity	NPC469689
0.72	Intermediate Similarity	NPC5674
0.715	Intermediate Similarity	NPC87363
0.7101	Intermediate Similarity	NPC283207
0.7072	Intermediate Similarity	NPC82056
0.7071	Intermediate Similarity	NPC470936
0.7059	Intermediate Similarity	NPC38964
0.7059	Intermediate Similarity	NPC99723
0.7014	Intermediate Similarity	NPC470646
0.7005	Intermediate Similarity	NPC257266
0.698	Remote Similarity	NPC129578
0.6977	Remote Similarity	NPC286135
0.6972	Remote Similarity	NPC257728
0.6972	Remote Similarity	NPC205926
0.697	Remote Similarity	NPC329743
0.697	Remote Similarity	NPC469479
0.6967	Remote Similarity	NPC85381
0.6952	Remote Similarity	NPC41122
0.6952	Remote Similarity	NPC318805
0.6948	Remote Similarity	NPC83019
0.6941	Remote Similarity	NPC153365
0.6938	Remote Similarity	NPC469437
0.6935	Remote Similarity	NPC73422
0.6935	Remote Similarity	NPC310399
0.6927	Remote Similarity	NPC327005
0.6923	Remote Similarity	NPC51543
0.6908	Remote Similarity	NPC138083
0.6905	Remote Similarity	NPC470642
0.6901	Remote Similarity	NPC204580
0.6901	Remote Similarity	NPC234318
0.6901	Remote Similarity	NPC144314
0.69	Remote Similarity	NPC90336
0.69	Remote Similarity	NPC469505
0.6889	Remote Similarity	NPC37957
0.6889	Remote Similarity	NPC153923
0.6884	Remote Similarity	NPC209473
0.6884	Remote Similarity	NPC475654
0.6884	Remote Similarity	NPC242728
0.6884	Remote Similarity	NPC254700
0.6881	Remote Similarity	NPC80472
0.6881	Remote Similarity	NPC474881
0.6878	Remote Similarity	NPC32064
0.6875	Remote Similarity	NPC212697
0.6869	Remote Similarity	NPC50548
0.6854	Remote Similarity	NPC149962
0.6847	Remote Similarity	NPC164608
0.6845	Remote Similarity	NPC309692
0.6837	Remote Similarity	NPC123859
0.681	Remote Similarity	NPC474009
0.6808	Remote Similarity	NPC264938
0.6804	Remote Similarity	NPC475768
0.6802	Remote Similarity	NPC92235
0.6798	Remote Similarity	NPC473748
0.6794	Remote Similarity	NPC276120
0.678	Remote Similarity	NPC228040
0.6779	Remote Similarity	NPC195538
0.6777	Remote Similarity	NPC64140
0.6777	Remote Similarity	NPC208890
0.6777	Remote Similarity	NPC174122
0.6774	Remote Similarity	NPC64576
0.6774	Remote Similarity	NPC201055
0.6774	Remote Similarity	NPC151470
0.6774	Remote Similarity	NPC254045
0.6771	Remote Similarity	NPC116178
0.6763	Remote Similarity	NPC329816
0.6762	Remote Similarity	NPC249996
0.6761	Remote Similarity	NPC94499
0.6761	Remote Similarity	NPC471825
0.6746	Remote Similarity	NPC476202
0.6744	Remote Similarity	NPC66909
0.6743	Remote Similarity	NPC311357
0.6741	Remote Similarity	NPC217903
0.673	Remote Similarity	NPC234069
0.673	Remote Similarity	NPC471395
0.673	Remote Similarity	NPC124626
0.6715	Remote Similarity	NPC149502
0.6715	Remote Similarity	NPC222665
0.6715	Remote Similarity	NPC271755
0.6715	Remote Similarity	NPC254071
0.6714	Remote Similarity	NPC473716
0.6714	Remote Similarity	NPC475597
0.6699	Remote Similarity	NPC315913
0.6699	Remote Similarity	NPC473562
0.6699	Remote Similarity	NPC263955
0.6699	Remote Similarity	NPC23593
0.6684	Remote Similarity	NPC9373
0.6682	Remote Similarity	NPC18306
0.6667	Remote Similarity	NPC20360
0.6667	Remote Similarity	NPC104196
0.6667	Remote Similarity	NPC29587
0.6667	Remote Similarity	NPC473378
0.6667	Remote Similarity	NPC54654
0.6667	Remote Similarity	NPC290005
0.6667	Remote Similarity	NPC473449
0.6667	Remote Similarity	NPC7715
0.6667	Remote Similarity	NPC181796
0.6667	Remote Similarity	NPC311973
0.6667	Remote Similarity	NPC185639
0.6667	Remote Similarity	NPC222661
0.6667	Remote Similarity	NPC90998
0.6667	Remote Similarity	NPC239824
0.6667	Remote Similarity	NPC258657
0.6667	Remote Similarity	NPC229373
0.6667	Remote Similarity	NPC49075
0.6667	Remote Similarity	NPC321166
0.6667	Remote Similarity	NPC271013
0.6667	Remote Similarity	NPC251735
0.6667	Remote Similarity	NPC217748
0.6667	Remote Similarity	NPC471675
0.6667	Remote Similarity	NPC8836
0.6667	Remote Similarity	NPC182052
0.6667	Remote Similarity	NPC279228
0.6667	Remote Similarity	NPC473407
0.6667	Remote Similarity	NPC285931
0.6667	Remote Similarity	NPC328155
0.6667	Remote Similarity	NPC15414
0.6667	Remote Similarity	NPC290582
0.6667	Remote Similarity	NPC223690
0.6667	Remote Similarity	NPC42663
0.6652	Remote Similarity	NPC315914
0.6651	Remote Similarity	NPC107739
0.6651	Remote Similarity	NPC212237
0.6651	Remote Similarity	NPC116465
0.6651	Remote Similarity	NPC314213
0.665	Remote Similarity	NPC476169
0.665	Remote Similarity	NPC206736
0.665	Remote Similarity	NPC92589
0.665	Remote Similarity	NPC88378
0.665	Remote Similarity	NPC476459
0.665	Remote Similarity	NPC195766
0.665	Remote Similarity	NPC211713
0.665	Remote Similarity	NPC198075
0.6636	Remote Similarity	NPC293624
0.6635	Remote Similarity	NPC83511
0.6635	Remote Similarity	NPC236089
0.6635	Remote Similarity	NPC274716
0.6635	Remote Similarity	NPC254441
0.6635	Remote Similarity	NPC116007
0.6635	Remote Similarity	NPC167116
0.6634	Remote Similarity	NPC204908
0.6634	Remote Similarity	NPC83198
0.6633	Remote Similarity	NPC476238
0.6633	Remote Similarity	NPC14875
0.6633	Remote Similarity	NPC327269
0.6633	Remote Similarity	NPC169742
0.6633	Remote Similarity	NPC31627
0.6632	Remote Similarity	NPC184607
0.6621	Remote Similarity	NPC316164
0.662	Remote Similarity	NPC22115
0.662	Remote Similarity	NPC33256
0.662	Remote Similarity	NPC275680
0.6619	Remote Similarity	NPC286119
0.6618	Remote Similarity	NPC152680
0.6618	Remote Similarity	NPC232386
0.6618	Remote Similarity	NPC190783
0.6618	Remote Similarity	NPC90984
0.6618	Remote Similarity	NPC474051
0.6616	Remote Similarity	NPC29777
0.6616	Remote Similarity	NPC471115
0.6606	Remote Similarity	NPC477666
0.6605	Remote Similarity	NPC24260
0.6604	Remote Similarity	NPC16357
0.6604	Remote Similarity	NPC95426
0.6604	Remote Similarity	NPC302245
0.6602	Remote Similarity	NPC82330
0.6601	Remote Similarity	NPC328649
0.6599	Remote Similarity	NPC478189
0.6593	Remote Similarity	NPC30749
0.6591	Remote Similarity	NPC119818
0.6591	Remote Similarity	NPC202771
0.6591	Remote Similarity	NPC328700
0.6591	Remote Similarity	NPC2173
0.6588	Remote Similarity	NPC315542
0.6588	Remote Similarity	NPC30779
0.6584	Remote Similarity	NPC65504
0.6583	Remote Similarity	NPC472636
0.6583	Remote Similarity	NPC471229
0.658	Remote Similarity	NPC250960

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 NPC14390 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	602
0.2-0.3	975
0.3-0.4	1927
0.4-0.5	2911
0.5-0.6	1975
0.6-0.7	430
0.7-0.8	16
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
0.74	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3473	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4377	Discontinued
0.7085	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4361	Phase 2
0.7005	Intermediate Similarity	NPD7584	Approved
0.7005	Intermediate Similarity	NPD7583	Approved
0.7	Intermediate Similarity	NPD4466	Phase 1
0.6995	Remote Similarity	NPD7810	Phase 3
0.6995	Remote Similarity	NPD7811	Phase 3
0.6972	Remote Similarity	NPD7585	Approved
0.6938	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8070	Approved
0.6905	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6997	Phase 2
0.6854	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.683	Remote Similarity	NPD7047	Phase 3
0.6825	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.682	Remote Similarity	NPD6863	Phase 2
0.6818	Remote Similarity	NPD5967	Approved
0.6812	Remote Similarity	NPD7549	Discontinued
0.6808	Remote Similarity	NPD4363	Phase 3
0.6808	Remote Similarity	NPD4360	Phase 2
0.6796	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7020	Approved
0.6788	Remote Similarity	NPD7019	Approved
0.6782	Remote Similarity	NPD7608	Discontinued
0.6777	Remote Similarity	NPD7861	Discontinued
0.6774	Remote Similarity	NPD2494	Approved
0.6774	Remote Similarity	NPD3452	Approved
0.6774	Remote Similarity	NPD2493	Approved
0.6774	Remote Similarity	NPD3450	Approved
0.677	Remote Similarity	NPD6198	Phase 1
0.6758	Remote Similarity	NPD4582	Approved
0.6758	Remote Similarity	NPD4583	Approved
0.6754	Remote Similarity	NPD7466	Approved
0.6751	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD6072	Discontinued
0.6748	Remote Similarity	NPD5557	Phase 1
0.6746	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2973	Approved
0.6744	Remote Similarity	NPD2975	Approved
0.6744	Remote Similarity	NPD2974	Approved
0.6732	Remote Similarity	NPD7177	Discontinued
0.6731	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4580	Approved
0.6712	Remote Similarity	NPD4002	Approved
0.6712	Remote Similarity	NPD4004	Approved
0.6701	Remote Similarity	NPD7447	Phase 1
0.6683	Remote Similarity	NPD6746	Phase 2
0.6667	Remote Similarity	NPD8053	Approved
0.6667	Remote Similarity	NPD8054	Approved
0.6652	Remote Similarity	NPD8161	Suspended
0.6651	Remote Similarity	NPD3490	Discontinued
0.6649	Remote Similarity	NPD7212	Phase 2
0.6649	Remote Similarity	NPD7213	Phase 3
0.6636	Remote Similarity	NPD3802	Phase 3
0.6636	Remote Similarity	NPD7497	Discontinued
0.6635	Remote Similarity	NPD3823	Discontinued
0.6633	Remote Similarity	NPD7131	Phase 3
0.6633	Remote Similarity	NPD7577	Discontinued
0.6622	Remote Similarity	NPD7827	Phase 1
0.6618	Remote Similarity	NPD6020	Phase 2
0.6618	Remote Similarity	NPD6747	Phase 1
0.6616	Remote Similarity	NPD6502	Phase 2
0.6609	Remote Similarity	NPD8059	Phase 3
0.6609	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7565	Approved
0.6605	Remote Similarity	NPD6181	Discontinued
0.6604	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5006	Approved
0.6591	Remote Similarity	NPD5005	Approved
0.6585	Remote Similarity	NPD2388	Discontinued
0.6583	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7291	Discontinued
0.6571	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3909	Discontinued
0.6562	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.654	Remote Similarity	NPD7280	Phase 3
0.654	Remote Similarity	NPD7281	Phase 3
0.6533	Remote Similarity	NPD4678	Approved
0.6533	Remote Similarity	NPD4675	Approved
0.6517	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5773	Approved
0.6517	Remote Similarity	NPD5772	Approved
0.6514	Remote Similarity	NPD5515	Phase 2
0.6512	Remote Similarity	NPD2488	Approved
0.6512	Remote Similarity	NPD2490	Approved
0.6505	Remote Similarity	NPD5242	Approved
0.6498	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.649	Remote Similarity	NPD8252	Approved
0.649	Remote Similarity	NPD8099	Discontinued
0.649	Remote Similarity	NPD8251	Approved
0.6488	Remote Similarity	NPD7199	Phase 2
0.6482	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7296	Approved
0.648	Remote Similarity	NPD4357	Discontinued
0.6477	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7225	Discontinued
0.6476	Remote Similarity	NPD6826	Discontinued
0.6473	Remote Similarity	NPD7263	Phase 2
0.6473	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD7248	Discontinued
0.6466	Remote Similarity	NPD7556	Discontinued
0.6465	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD8156	Discontinued
0.6458	Remote Similarity	NPD7048	Phase 3
0.6458	Remote Similarity	NPD4846	Phase 2
0.6446	Remote Similarity	NPD7417	Discontinued
0.6443	Remote Similarity	NPD2654	Approved
0.6442	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7654	Discontinued
0.6439	Remote Similarity	NPD2904	Discontinued
0.6432	Remote Similarity	NPD4210	Discontinued
0.6429	Remote Similarity	NPD6667	Approved
0.6429	Remote Similarity	NPD6666	Approved
0.6426	Remote Similarity	NPD7224	Discontinued
0.6426	Remote Similarity	NPD7223	Discontinued
0.6425	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6971	Discontinued
0.6422	Remote Similarity	NPD7669	Phase 3
0.6422	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD4157	Discontinued
0.6419	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD7906	Approved
0.6419	Remote Similarity	NPD1898	Discontinued
0.6418	Remote Similarity	NPD3778	Approved
0.6413	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5481	Discontinued
0.6409	Remote Similarity	NPD4420	Approved
0.6408	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD8469	Approved
0.6397	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7476	Discontinued
0.6389	Remote Similarity	NPD6836	Approved
0.6385	Remote Similarity	NPD4578	Approved
0.6385	Remote Similarity	NPD2968	Approved
0.6385	Remote Similarity	NPD4577	Approved
0.6385	Remote Similarity	NPD2971	Approved
0.6382	Remote Similarity	NPD7427	Discontinued
0.6382	Remote Similarity	NPD1670	Discontinued
0.638	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.638	Remote Similarity	NPD6874	Approved
0.6377	Remote Similarity	NPD7315	Approved
0.6376	Remote Similarity	NPD7125	Discontinued
0.6373	Remote Similarity	NPD6788	Approved
0.6373	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4663	Approved
0.6372	Remote Similarity	NPD7391	Discontinued
0.6368	Remote Similarity	NPD7039	Approved
0.6368	Remote Similarity	NPD7038	Approved
0.6364	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.636	Remote Similarity	NPD7801	Approved
0.6355	Remote Similarity	NPD7972	Discontinued
0.6355	Remote Similarity	NPD2801	Approved
0.6348	Remote Similarity	NPD7930	Approved
0.6348	Remote Similarity	NPD7559	Phase 2
0.6343	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6386	Approved
0.6337	Remote Similarity	NPD6385	Approved
0.6337	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7110	Phase 1
0.6333	Remote Similarity	NPD6625	Approved
0.633	Remote Similarity	NPD3819	Phase 2
0.6329	Remote Similarity	NPD7484	Phase 3
0.6329	Remote Similarity	NPD7485	Phase 3
0.6327	Remote Similarity	NPD6296	Discontinued
0.6325	Remote Similarity	NPD7907	Approved
0.6324	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD2415	Discontinued
0.6323	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD4005	Discontinued
0.6318	Remote Similarity	NPD824	Approved
0.6316	Remote Similarity	NPD5914	Approved
0.6316	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.631	Remote Similarity	NPD8461	Discontinued
0.6309	Remote Similarity	NPD2899	Discontinued
0.6309	Remote Similarity	NPD4665	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