NPASS Compound

Structure

CID141385 OpenBabel06191715502D 36 41 0 0 1 0 0 0 0 0999 V2000 2.8311 -2.1568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5378 -2.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1360 -0.5620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3010 -1.6627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5250 0.6447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7756 0.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0534 1.1685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5223 0.8716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2699 -0.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9507 -0.3754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2866 1.7982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1452 -1.8515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4096 -0.0507 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6196 0.0586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2060 -0.3940 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9338 -0.2469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6011 -0.0001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3006 -0.7509 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9507 1.1264 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6502 1.1263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6501 -1.1263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9508 -1.1263 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9509 0.3753 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6502 0.3753 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3004 -0.0001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8278 0.1858 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9726 2.4805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3413 -1.2719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8555 -0.9936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6503 1.9755 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1822 -1.8350 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1017 -2.5972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6864 0.7998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5649 -0.4245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3263 0.1943 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 12 1 0 0 0 0 2 12 1 0 0 0 0 4 18 1 0 0 0 0 5 7 1 0 0 0 0 5 13 1 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 20 1 0 0 0 0 8 26 1 0 0 0 0 9 14 2 0 0 0 0 9 26 1 0 0 0 0 10 19 1 0 0 0 0 11 19 1 0 0 0 0 11 27 1 0 0 0 0 12 22 1 0 0 0 0 13 3 1 1 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 24 1 6 0 0 0 15 28 1 0 0 0 0 16 29 2 0 0 0 0 16 35 1 0 0 0 0 17 22 1 6 0 0 0 17 23 1 0 0 0 0 17 35 1 0 0 0 0 18 21 1 6 0 0 0 19 20 1 1 0 0 0 20 24 1 1 0 0 0 20 30 1 0 0 0 0 21 10 1 6 0 0 0 21 31 1 0 0 0 0 21 36 1 0 0 0 0 22 18 1 6 0 0 0 22 32 1 0 0 0 0 23 19 1 6 0 0 0 23 25 1 0 0 0 0 23 33 1 0 0 0 0 24 25 1 6 0 0 0 24 36 1 0 0 0 0 25 18 1 6 0 0 0 25 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	509.23
Volume:	480.607
LogP:	1.172
LogD:	0.179
LogS:	-2.891
# Rotatable Bonds:	5
TPSA:	192.93
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.228
Synthetic Accessibility Score:	7.466
Fsp3:	0.8
Lipinski Rule-of-5:	Rejected
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:	-6.213
MDCK Permeability:	1.7429687432013452e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.551
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.155
Plasma Protein Binding (PPB):	34.860496520996094%
Volume Distribution (VD):	0.406
Pgp-substrate:	48.068843841552734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.322
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.307
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	1.531
Half-life (T1/2):	0.476

ADMET: Toxicity

hERG Blockers:	0.091
Human Hepatotoxicity (H-HT):	0.773
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.771
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.07
Skin Sensitization:	0.906
Carcinogencity:	0.961
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC141385

Natural Product ID:	NPC141385
*Common Name:**	Spiganthine
IUPAC Name:	n.a.
Synonyms:	spiganthine
Standard InCHIKey:	CAJJMEFYDCCPAX-SFEDZAPPSA-N
Standard InCHI:	InChI=1S/C25H35NO10/c1-12(2)22(32)17(35-16(29)14-6-8-26-9-14)23(33)19(11-27)10-21(31)18(22,4)25(23,34)24(36-21)15(28)13(3)5-7-20(19,24)30/h6,8-9,12-13,15,17,26-28,30-34H,5,7,10-11H2,1-4H3/t13-,15+,17+,18-,19+,20-,21-,22+,23+,24+,25+/m0/s1
SMILES:	CC(C)[C@]1([C@H]([C@]2([C@]3(C[C@]4([C@]1(C)[C@@]2([C@]1([C@@H]([C@@H](C)CC[C@]31O)O)O4)O)O)CO)O)OC(=O)c1cc[nH]c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463332
PubChem CID:	12041874
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO5794	Spigelia anthelmia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5794	Spigelia anthelmia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5794	Spigelia anthelmia	Species	Loganiaceae	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
EC50	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.	EC50	=	60.0	nM	PMID[509001]

☑ 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 NPC141385 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	367
0.1-0.2	1803
0.2-0.3	5240
0.3-0.4	22071
0.4-0.5	10705
0.5-0.6	2177
0.6-0.7	177
0.7-0.8	154
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.808	Intermediate Similarity	NPC37473
0.7742	Intermediate Similarity	NPC475408
0.7742	Intermediate Similarity	NPC471014
0.7706	Intermediate Similarity	NPC294579
0.7706	Intermediate Similarity	NPC144779
0.7696	Intermediate Similarity	NPC470306
0.7661	Intermediate Similarity	NPC6981
0.7661	Intermediate Similarity	NPC471016
0.7658	Intermediate Similarity	NPC475137
0.7658	Intermediate Similarity	NPC475498
0.7639	Intermediate Similarity	NPC472553
0.7639	Intermediate Similarity	NPC476467
0.7615	Intermediate Similarity	NPC477910
0.7613	Intermediate Similarity	NPC76565
0.7591	Intermediate Similarity	NPC301368
0.7591	Intermediate Similarity	NPC84815
0.7581	Intermediate Similarity	NPC304179
0.7581	Intermediate Similarity	NPC472550
0.7581	Intermediate Similarity	NPC48042
0.7556	Intermediate Similarity	NPC470486
0.7556	Intermediate Similarity	NPC471190
0.7556	Intermediate Similarity	NPC471977
0.7556	Intermediate Similarity	NPC475644
0.7535	Intermediate Similarity	NPC63041
0.7534	Intermediate Similarity	NPC471980
0.7511	Intermediate Similarity	NPC475631
0.7511	Intermediate Similarity	NPC476110
0.7511	Intermediate Similarity	NPC475600
0.7511	Intermediate Similarity	NPC87152
0.75	Intermediate Similarity	NPC238278
0.75	Intermediate Similarity	NPC473850
0.7489	Intermediate Similarity	NPC228331
0.7489	Intermediate Similarity	NPC127720
0.7489	Intermediate Similarity	NPC127026
0.7489	Intermediate Similarity	NPC319128
0.7478	Intermediate Similarity	NPC475362
0.7467	Intermediate Similarity	NPC473506
0.7466	Intermediate Similarity	NPC62367
0.7456	Intermediate Similarity	NPC30456
0.7455	Intermediate Similarity	NPC250807
0.7455	Intermediate Similarity	NPC57797
0.7434	Intermediate Similarity	NPC146824
0.7432	Intermediate Similarity	NPC472555
0.7432	Intermediate Similarity	NPC216428
0.7422	Intermediate Similarity	NPC477902
0.7422	Intermediate Similarity	NPC233727
0.7422	Intermediate Similarity	NPC328154
0.7412	Intermediate Similarity	NPC475303
0.7412	Intermediate Similarity	NPC475596
0.7409	Intermediate Similarity	NPC4421
0.7391	Intermediate Similarity	NPC170751
0.7376	Intermediate Similarity	NPC42678
0.7376	Intermediate Similarity	NPC477909
0.7376	Intermediate Similarity	NPC477907
0.7366	Intermediate Similarity	NPC477912
0.7364	Intermediate Similarity	NPC41724
0.7364	Intermediate Similarity	NPC51008
0.7357	Intermediate Similarity	NPC122968
0.7357	Intermediate Similarity	NPC328186
0.7357	Intermediate Similarity	NPC475601
0.7357	Intermediate Similarity	NPC477787
0.7357	Intermediate Similarity	NPC124029
0.7357	Intermediate Similarity	NPC228377
0.7357	Intermediate Similarity	NPC211920
0.7348	Intermediate Similarity	NPC237702
0.7342	Intermediate Similarity	NPC477908
0.7342	Intermediate Similarity	NPC206343
0.7336	Intermediate Similarity	NPC473689
0.7336	Intermediate Similarity	NPC150698
0.7336	Intermediate Similarity	NPC292416
0.7336	Intermediate Similarity	NPC96801
0.7333	Intermediate Similarity	NPC477911
0.733	Intermediate Similarity	NPC264674
0.7318	Intermediate Similarity	NPC323551
0.7318	Intermediate Similarity	NPC280473
0.7316	Intermediate Similarity	NPC35208
0.7316	Intermediate Similarity	NPC327769
0.7316	Intermediate Similarity	NPC475426
0.7313	Intermediate Similarity	NPC148860
0.7309	Intermediate Similarity	NPC212768
0.7309	Intermediate Similarity	NPC6576
0.7309	Intermediate Similarity	NPC158020
0.7309	Intermediate Similarity	NPC473089
0.7309	Intermediate Similarity	NPC473115
0.7309	Intermediate Similarity	NPC75600
0.7304	Intermediate Similarity	NPC319880
0.7304	Intermediate Similarity	NPC244839
0.7304	Intermediate Similarity	NPC469748
0.7304	Intermediate Similarity	NPC320324
0.7281	Intermediate Similarity	NPC285411
0.7281	Intermediate Similarity	NPC14116
0.7261	Intermediate Similarity	NPC316841
0.7261	Intermediate Similarity	NPC477906
0.7249	Intermediate Similarity	NPC134384
0.7249	Intermediate Similarity	NPC311196
0.7241	Intermediate Similarity	NPC475406
0.7229	Intermediate Similarity	NPC213143
0.7215	Intermediate Similarity	NPC476090
0.721	Intermediate Similarity	NPC38959
0.721	Intermediate Similarity	NPC327904
0.7207	Intermediate Similarity	NPC165837
0.7181	Intermediate Similarity	NPC477788
0.7143	Intermediate Similarity	NPC193361
0.7143	Intermediate Similarity	NPC62844
0.7137	Intermediate Similarity	NPC477903
0.7119	Intermediate Similarity	NPC253482
0.7117	Intermediate Similarity	NPC40919
0.7117	Intermediate Similarity	NPC470189
0.7105	Intermediate Similarity	NPC235364
0.7104	Intermediate Similarity	NPC472752
0.7071	Intermediate Similarity	NPC180668
0.7071	Intermediate Similarity	NPC471013
0.7071	Intermediate Similarity	NPC148896
0.7051	Intermediate Similarity	NPC470279
0.7043	Intermediate Similarity	NPC477900
0.7043	Intermediate Similarity	NPC477899
0.7043	Intermediate Similarity	NPC26881
0.7042	Intermediate Similarity	NPC475533
0.7029	Intermediate Similarity	NPC475648
0.7025	Intermediate Similarity	NPC10904
0.7018	Intermediate Similarity	NPC477901
0.7012	Intermediate Similarity	NPC475315
0.7012	Intermediate Similarity	NPC324619
0.7004	Intermediate Similarity	NPC319556
0.7004	Intermediate Similarity	NPC187494
0.6982	Remote Similarity	NPC470190
0.698	Remote Similarity	NPC475301
0.698	Remote Similarity	NPC326930
0.696	Remote Similarity	NPC162812
0.6939	Remote Similarity	NPC471015
0.6923	Remote Similarity	NPC91125
0.6916	Remote Similarity	NPC207531
0.6885	Remote Similarity	NPC476516
0.6883	Remote Similarity	NPC13603
0.6867	Remote Similarity	NPC473833
0.6842	Remote Similarity	NPC30570
0.6842	Remote Similarity	NPC85879
0.6842	Remote Similarity	NPC53255
0.6813	Remote Similarity	NPC471978
0.6813	Remote Similarity	NPC328928
0.6786	Remote Similarity	NPC475835
0.6784	Remote Similarity	NPC292517
0.6771	Remote Similarity	NPC477043
0.6732	Remote Similarity	NPC471979
0.6723	Remote Similarity	NPC471004
0.6696	Remote Similarity	NPC289086
0.6667	Remote Similarity	NPC309498
0.6652	Remote Similarity	NPC477044
0.6652	Remote Similarity	NPC477041
0.6637	Remote Similarity	NPC32451
0.6625	Remote Similarity	NPC70155
0.6622	Remote Similarity	NPC477045
0.661	Remote Similarity	NPC235885
0.6609	Remote Similarity	NPC475476
0.6609	Remote Similarity	NPC242446
0.659	Remote Similarity	NPC209917
0.6585	Remote Similarity	NPC476517
0.6571	Remote Similarity	NPC470843
0.6571	Remote Similarity	NPC94541
0.6569	Remote Similarity	NPC473806
0.6569	Remote Similarity	NPC471634
0.6562	Remote Similarity	NPC328559
0.654	Remote Similarity	NPC141428
0.6534	Remote Similarity	NPC131273
0.6534	Remote Similarity	NPC473441
0.6533	Remote Similarity	NPC475223
0.6524	Remote Similarity	NPC249428
0.6513	Remote Similarity	NPC79107
0.6513	Remote Similarity	NPC475424
0.6509	Remote Similarity	NPC471284
0.6504	Remote Similarity	NPC475448
0.6504	Remote Similarity	NPC246983
0.6502	Remote Similarity	NPC320748
0.6502	Remote Similarity	NPC324245
0.6494	Remote Similarity	NPC235900
0.6485	Remote Similarity	NPC57690
0.6483	Remote Similarity	NPC2395
0.6481	Remote Similarity	NPC204491
0.6466	Remote Similarity	NPC473547
0.6455	Remote Similarity	NPC138370
0.6444	Remote Similarity	NPC79223
0.6438	Remote Similarity	NPC473650
0.6438	Remote Similarity	NPC160527
0.6438	Remote Similarity	NPC97388
0.6429	Remote Similarity	NPC317672
0.6405	Remote Similarity	NPC282033
0.6398	Remote Similarity	NPC74360
0.6395	Remote Similarity	NPC229348
0.6392	Remote Similarity	NPC194541
0.6391	Remote Similarity	NPC127677
0.6386	Remote Similarity	NPC311451
0.6384	Remote Similarity	NPC329024
0.6383	Remote Similarity	NPC96131
0.6375	Remote Similarity	NPC267926
0.6368	Remote Similarity	NPC21483
0.6368	Remote Similarity	NPC198205
0.636	Remote Similarity	NPC266192
0.636	Remote Similarity	NPC473667
0.6356	Remote Similarity	NPC471583
0.6356	Remote Similarity	NPC311054

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 NPC141385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	585
0.2-0.3	1352
0.3-0.4	3743
0.4-0.5	2715
0.5-0.6	545
0.6-0.7	11
0.7-0.8	0
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
0.6971	Remote Similarity	NPD8468	Phase 2
0.6756	Remote Similarity	NPD2509	Approved
0.6756	Remote Similarity	NPD2510	Approved
0.6504	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3394	Approved
0.6481	Remote Similarity	NPD3393	Approved
0.6481	Remote Similarity	NPD3389	Approved
0.6404	Remote Similarity	NPD7396	Approved
0.6395	Remote Similarity	NPD3795	Approved
0.6395	Remote Similarity	NPD3794	Approved
0.6372	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD3006	Discontinued
0.61	Remote Similarity	NPD3280	Approved
0.6094	Remote Similarity	NPD7010	Phase 3
0.6067	Remote Similarity	NPD8160	Phase 2
0.6056	Remote Similarity	NPD6635	Approved
0.6052	Remote Similarity	NPD3947	Discontinued
0.6043	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7470	Discontinued
0.6017	Remote Similarity	NPD4506	Discontinued
0.5976	Remote Similarity	NPD5891	Approved
0.5957	Remote Similarity	NPD7957	Phase 1
0.5957	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD6529	Discontinued
0.5946	Remote Similarity	NPD3178	Discontinued
0.5943	Remote Similarity	NPD820	Phase 3
0.5941	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6770	Approved
0.5918	Remote Similarity	NPD6995	Phase 1
0.5909	Remote Similarity	NPD7708	Approved
0.5909	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD8326	Phase 3
0.5909	Remote Similarity	NPD8325	Phase 3
0.5907	Remote Similarity	NPD8399	Phase 1
0.5907	Remote Similarity	NPD8423	Phase 2
0.59	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5475	Discontinued
0.5892	Remote Similarity	NPD7707	Approved
0.589	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.588	Remote Similarity	NPD7803	Approved
0.5872	Remote Similarity	NPD6176	Phase 1
0.5872	Remote Similarity	NPD8072	Approved
0.5847	Remote Similarity	NPD5901	Discontinued
0.583	Remote Similarity	NPD8073	Approved
0.5826	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD6026	Approved
0.582	Remote Similarity	NPD7878	Phase 2
0.5819	Remote Similarity	NPD5003	Discontinued
0.5817	Remote Similarity	NPD7688	Phase 1
0.5817	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.5813	Remote Similarity	NPD4301	Approved
0.5811	Remote Similarity	NPD7955	Approved
0.5811	Remote Similarity	NPD7956	Approved
0.5811	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD7069	Discontinued
0.5806	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.5801	Remote Similarity	NPD4427	Phase 2
0.5798	Remote Similarity	NPD1483	Discontinued
0.5771	Remote Similarity	NPD7558	Phase 2
0.5763	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.5756	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.5756	Remote Similarity	NPD8364	Approved
0.5756	Remote Similarity	NPD8363	Approved
0.5745	Remote Similarity	NPD8465	Approved
0.5745	Remote Similarity	NPD8467	Approved
0.5745	Remote Similarity	NPD8466	Approved
0.5744	Remote Similarity	NPD8097	Phase 3
0.5744	Remote Similarity	NPD8096	Phase 3
0.5725	Remote Similarity	NPD5482	Discontinued
0.5721	Remote Similarity	NPD7234	Approved
0.5721	Remote Similarity	NPD7233	Approved
0.572	Remote Similarity	NPD8289	Discontinued
0.5714	Remote Similarity	NPD4376	Phase 3
0.5714	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.5709	Remote Similarity	NPD1996	Discontinued
0.5709	Remote Similarity	NPD6242	Discontinued
0.5709	Remote Similarity	NPD8479	Phase 2
0.5708	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD3915	Approved
0.5702	Remote Similarity	NPD5066	Phase 2
0.5702	Remote Similarity	NPD5067	Phase 2
0.5702	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD2565	Phase 2
0.5696	Remote Similarity	NPD2564	Approved
0.5692	Remote Similarity	NPD7967	Discontinued
0.569	Remote Similarity	NPD6361	Phase 2
0.5688	Remote Similarity	NPD8427	Approved
0.5688	Remote Similarity	NPD8428	Approved
0.5688	Remote Similarity	NPD8429	Approved
0.5685	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD3918	Approved
0.5679	Remote Similarity	NPD3917	Approved
0.5679	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD5612	Discontinued
0.5663	Remote Similarity	NPD8460	Approved
0.5663	Remote Similarity	NPD8425	Approved
0.5663	Remote Similarity	NPD8459	Approved
0.5663	Remote Similarity	NPD8426	Approved
0.5659	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5022	Discontinued
0.5649	Remote Similarity	NPD8282	Approved
0.5649	Remote Similarity	NPD56	Approved
0.5649	Remote Similarity	NPD6987	Phase 1
0.5649	Remote Similarity	NPD8283	Approved
0.5644	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD4417	Approved
0.5635	Remote Similarity	NPD4086	Phase 1
0.5632	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD485	Clinical (unspecified phase)
0.563	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD5632	Approved
0.5628	Remote Similarity	NPD8063	Discontinued
0.5622	Remote Similarity	NPD4526	Approved
0.5622	Remote Similarity	NPD4528	Approved
0.5622	Remote Similarity	NPD4529	Approved
0.5616	Remote Similarity	NPD5088	Discontinued
0.5614	Remote Similarity	NPD2091	Phase 2
0.5614	Remote Similarity	NPD2096	Phase 2
0.5613	Remote Similarity	NPD6530	Approved
0.5613	Remote Similarity	NPD6531	Approved
0.5613	Remote Similarity	NPD9271	Approved
0.5609	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.5605	Remote Similarity	NPD8105	Discontinued
0.5602	Remote Similarity	NPD1392	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