NPASS Compound

Structure

NPC475879 OpenBabel07101719142D 30 30 0 0 1 0 0 0 0 0999 V2000 -0.0486 6.8111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2688 4.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9930 10.9607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1716 9.5517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4444 5.6885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2242 8.4291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0823 2.2433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4499 5.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8511 4.7749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6309 7.5155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6701 3.0523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8120 9.2381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 2.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4107 10.2562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0431 6.7065 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2634 3.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4052 10.1517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5783 10.4652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0040 11.1697 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9905 11.2743 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5728 10.5698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5918 11.9787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3973 12.1878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 0.2788 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 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 21 1 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 16 1 1 6 0 0 0 19 23 1 0 0 0 0 19 25 2 0 0 0 0 20 24 1 0 0 0 0 21 23 1 0 0 0 0 21 26 1 0 0 0 0 22 27 2 0 0 0 0 22 30 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.25
Volume:	452.026
LogP:	3.126
LogD:	2.669
LogS:	-3.87
# Rotatable Bonds:	14
TPSA:	107.97
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.293
Synthetic Accessibility Score:	4.546
Fsp3:	0.583
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.897
MDCK Permeability:	2.0934945496264845e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.235
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.368

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	95.7447280883789%
Volume Distribution (VD):	0.358
Pgp-substrate:	3.4764084815979004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.23
CYP1A2-substrate:	0.722
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.712
CYP2C9-substrate:	0.978
CYP2D6-inhibitor:	0.364
CYP2D6-substrate:	0.884
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	3.38
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.219
Drug-inuced Liver Injury (DILI):	0.67
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.756
Skin Sensitization:	0.633
Carcinogencity:	0.742
Eye Corrosion:	0.004
Eye Irritation:	0.033
Respiratory Toxicity:	0.698

Download Data

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

Natural Product: NPC475879

Natural Product ID:	NPC475879
*Common Name:**	Sarcotin O
IUPAC Name:	3-[(4E,6E,8S,11Z)-14,15-dihydroxy-4,8,12-trimethyl-16-oxoheptadeca-4,6,11-trienyl]-2-hydroxy-2H-furan-5-one
Synonyms:	Sarcotin O
Standard InCHIKey:	QWSRTOLIHWJYKS-MYSNFVLMSA-N
Standard InCHI:	InChI=1S/C24H36O6/c1-16(10-6-12-18(3)14-21(26)23(28)19(4)25)8-5-9-17(2)11-7-13-20-15-22(27)30-24(20)29/h5,8-9,12,15-16,21,23-24,26,28-29H,6-7,10-11,13-14H2,1-4H3/b8-5+,17-9+,18-12-/t16-,21?,23?,24?/m1/s1
SMILES:	C[C@@H](CC/C=C(CC(C(C(=O)C)O)O)/C)/C=C/C=C(/CCCC1=CC(=O)OC1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517885
PubChem CID:	10477236
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33166	Sarcotragus	Genus	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640517]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	6.8	ug ml-1	PMID[506171]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	14.9	ug ml-1	PMID[506171]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	3.0	ug ml-1	PMID[506171]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	11.5	ug ml-1	PMID[506171]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	4.6	ug ml-1	PMID[506171]

☑ 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 NPC475879 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	197
0.1-0.2	1227
0.2-0.3	5136
0.3-0.4	11481
0.4-0.5	14995
0.5-0.6	6733
0.6-0.7	2552
0.7-0.8	366
0.8-0.85	8
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC45409
0.8462	Intermediate Similarity	NPC475995
0.8462	Intermediate Similarity	NPC474098
0.8242	Intermediate Similarity	NPC475739
0.8202	Intermediate Similarity	NPC475706
0.8022	Intermediate Similarity	NPC261721
0.8021	Intermediate Similarity	NPC473291
0.7912	Intermediate Similarity	NPC474424
0.7895	Intermediate Similarity	NPC469692
0.7895	Intermediate Similarity	NPC469645
0.7889	Intermediate Similarity	NPC475714
0.7889	Intermediate Similarity	NPC16488
0.7872	Intermediate Similarity	NPC316228
0.7857	Intermediate Similarity	NPC161855
0.7826	Intermediate Similarity	NPC316426
0.7826	Intermediate Similarity	NPC315395
0.7812	Intermediate Similarity	NPC121825
0.7791	Intermediate Similarity	NPC260396
0.7778	Intermediate Similarity	NPC471296
0.7745	Intermediate Similarity	NPC469852
0.7732	Intermediate Similarity	NPC476488
0.7732	Intermediate Similarity	NPC476487
0.7674	Intermediate Similarity	NPC315843
0.767	Intermediate Similarity	NPC469853
0.7667	Intermediate Similarity	NPC112868
0.764	Intermediate Similarity	NPC99651
0.7634	Intermediate Similarity	NPC469910
0.76	Intermediate Similarity	NPC469864
0.76	Intermediate Similarity	NPC469872
0.7582	Intermediate Similarity	NPC474439
0.7582	Intermediate Similarity	NPC474028
0.7556	Intermediate Similarity	NPC47653
0.7528	Intermediate Similarity	NPC108816
0.7528	Intermediate Similarity	NPC93763
0.7527	Intermediate Similarity	NPC471300
0.7527	Intermediate Similarity	NPC261380
0.7527	Intermediate Similarity	NPC470755
0.7527	Intermediate Similarity	NPC11804
0.7527	Intermediate Similarity	NPC474860
0.7526	Intermediate Similarity	NPC282644
0.7526	Intermediate Similarity	NPC29798
0.7525	Intermediate Similarity	NPC469851
0.7525	Intermediate Similarity	NPC472753
0.75	Intermediate Similarity	NPC473311
0.75	Intermediate Similarity	NPC229799
0.75	Intermediate Similarity	NPC473448
0.75	Intermediate Similarity	NPC161045
0.75	Intermediate Similarity	NPC284472
0.75	Intermediate Similarity	NPC286770
0.7474	Intermediate Similarity	NPC476803
0.7473	Intermediate Similarity	NPC325031
0.7471	Intermediate Similarity	NPC227396
0.7471	Intermediate Similarity	NPC107654
0.7451	Intermediate Similarity	NPC472754
0.7449	Intermediate Similarity	NPC469632
0.7447	Intermediate Similarity	NPC469483
0.7447	Intermediate Similarity	NPC472009
0.7444	Intermediate Similarity	NPC321728
0.7442	Intermediate Similarity	NPC316185
0.7426	Intermediate Similarity	NPC477720
0.7419	Intermediate Similarity	NPC158756
0.7419	Intermediate Similarity	NPC161670
0.7416	Intermediate Similarity	NPC7563
0.7416	Intermediate Similarity	NPC320630
0.7416	Intermediate Similarity	NPC116177
0.7412	Intermediate Similarity	NPC475004
0.7404	Intermediate Similarity	NPC472749
0.7404	Intermediate Similarity	NPC472751
0.74	Intermediate Similarity	NPC208094
0.74	Intermediate Similarity	NPC475709
0.7396	Intermediate Similarity	NPC139418
0.7396	Intermediate Similarity	NPC14901
0.7396	Intermediate Similarity	NPC130359
0.7391	Intermediate Similarity	NPC475046
0.7391	Intermediate Similarity	NPC474959
0.7391	Intermediate Similarity	NPC85772
0.7391	Intermediate Similarity	NPC324170
0.7391	Intermediate Similarity	NPC310450
0.7391	Intermediate Similarity	NPC11383
0.7391	Intermediate Similarity	NPC471298
0.7379	Intermediate Similarity	NPC472755
0.7379	Intermediate Similarity	NPC472750
0.7379	Intermediate Similarity	NPC472747
0.7374	Intermediate Similarity	NPC209355
0.7368	Intermediate Similarity	NPC472007
0.7368	Intermediate Similarity	NPC475678
0.7368	Intermediate Similarity	NPC471738
0.7356	Intermediate Similarity	NPC144419
0.7353	Intermediate Similarity	NPC133907
0.7353	Intermediate Similarity	NPC128733
0.7353	Intermediate Similarity	NPC46998
0.7353	Intermediate Similarity	NPC110443
0.7353	Intermediate Similarity	NPC185141
0.7347	Intermediate Similarity	NPC242069
0.7347	Intermediate Similarity	NPC59646
0.7347	Intermediate Similarity	NPC11456
0.734	Intermediate Similarity	NPC475034
0.734	Intermediate Similarity	NPC67081
0.734	Intermediate Similarity	NPC21469
0.734	Intermediate Similarity	NPC471494
0.734	Intermediate Similarity	NPC471223
0.7333	Intermediate Similarity	NPC267231
0.7333	Intermediate Similarity	NPC182292
0.7333	Intermediate Similarity	NPC279532
0.7333	Intermediate Similarity	NPC127526
0.7326	Intermediate Similarity	NPC473361
0.7326	Intermediate Similarity	NPC329904
0.732	Intermediate Similarity	NPC473904
0.732	Intermediate Similarity	NPC3436
0.732	Intermediate Similarity	NPC232426
0.732	Intermediate Similarity	NPC474232
0.732	Intermediate Similarity	NPC313670
0.732	Intermediate Similarity	NPC281942
0.7315	Intermediate Similarity	NPC66108
0.7312	Intermediate Similarity	NPC169575
0.7312	Intermediate Similarity	NPC40746
0.7312	Intermediate Similarity	NPC253801
0.7312	Intermediate Similarity	NPC144415
0.7312	Intermediate Similarity	NPC471297
0.7308	Intermediate Similarity	NPC472748
0.7308	Intermediate Similarity	NPC472756
0.7303	Intermediate Similarity	NPC16279
0.7303	Intermediate Similarity	NPC256640
0.7303	Intermediate Similarity	NPC205615
0.7294	Intermediate Similarity	NPC474823
0.7292	Intermediate Similarity	NPC476805
0.7292	Intermediate Similarity	NPC472008
0.7292	Intermediate Similarity	NPC475819
0.7283	Intermediate Similarity	NPC42470
0.7282	Intermediate Similarity	NPC473596
0.7273	Intermediate Similarity	NPC470686
0.7273	Intermediate Similarity	NPC470521
0.7273	Intermediate Similarity	NPC477241
0.7273	Intermediate Similarity	NPC475832
0.7273	Intermediate Similarity	NPC470255
0.7273	Intermediate Similarity	NPC475927
0.7273	Intermediate Similarity	NPC65829
0.7264	Intermediate Similarity	NPC327106
0.7263	Intermediate Similarity	NPC308412
0.7263	Intermediate Similarity	NPC279267
0.7263	Intermediate Similarity	NPC311163
0.7263	Intermediate Similarity	NPC211892
0.7263	Intermediate Similarity	NPC210218
0.7263	Intermediate Similarity	NPC204686
0.7263	Intermediate Similarity	NPC219498
0.7263	Intermediate Similarity	NPC473687
0.7263	Intermediate Similarity	NPC69082
0.7263	Intermediate Similarity	NPC134807
0.7263	Intermediate Similarity	NPC164393
0.7263	Intermediate Similarity	NPC134885
0.7255	Intermediate Similarity	NPC324667
0.7245	Intermediate Similarity	NPC32552
0.7245	Intermediate Similarity	NPC141831
0.7245	Intermediate Similarity	NPC472199
0.7245	Intermediate Similarity	NPC470520
0.7234	Intermediate Similarity	NPC471301
0.7234	Intermediate Similarity	NPC31086
0.7228	Intermediate Similarity	NPC53844
0.7228	Intermediate Similarity	NPC471462
0.7216	Intermediate Similarity	NPC225283
0.7216	Intermediate Similarity	NPC212598
0.7212	Intermediate Similarity	NPC475871
0.7212	Intermediate Similarity	NPC475945
0.7209	Intermediate Similarity	NPC236208
0.7204	Intermediate Similarity	NPC473712
0.7204	Intermediate Similarity	NPC94875
0.7204	Intermediate Similarity	NPC180363
0.7204	Intermediate Similarity	NPC329829
0.7204	Intermediate Similarity	NPC473529
0.7204	Intermediate Similarity	NPC145914
0.7204	Intermediate Similarity	NPC65930
0.7204	Intermediate Similarity	NPC11332
0.7204	Intermediate Similarity	NPC26624
0.7204	Intermediate Similarity	NPC323251
0.7204	Intermediate Similarity	NPC73310
0.7204	Intermediate Similarity	NPC473780
0.7204	Intermediate Similarity	NPC475159
0.7204	Intermediate Similarity	NPC131002
0.72	Intermediate Similarity	NPC295347
0.72	Intermediate Similarity	NPC300710
0.72	Intermediate Similarity	NPC272050
0.7196	Intermediate Similarity	NPC38154
0.7196	Intermediate Similarity	NPC47951
0.7191	Intermediate Similarity	NPC478193
0.7191	Intermediate Similarity	NPC315552
0.7191	Intermediate Similarity	NPC478195
0.7191	Intermediate Similarity	NPC161038
0.7191	Intermediate Similarity	NPC478196
0.7191	Intermediate Similarity	NPC478194
0.7191	Intermediate Similarity	NPC478192
0.7191	Intermediate Similarity	NPC478191
0.7191	Intermediate Similarity	NPC329826
0.7191	Intermediate Similarity	NPC469414
0.7188	Intermediate Similarity	NPC477959
0.7188	Intermediate Similarity	NPC475037
0.7188	Intermediate Similarity	NPC72513
0.7188	Intermediate Similarity	NPC179659
0.7188	Intermediate Similarity	NPC160138
0.7188	Intermediate Similarity	NPC316138
0.7188	Intermediate Similarity	NPC86005

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 NPC475879 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1705
0.2-0.3	3734
0.3-0.4	2409
0.4-0.5	835
0.5-0.6	243
0.6-0.7	46
0.7-0.8	4
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
0.732	Intermediate Similarity	NPD5785	Approved
0.7245	Intermediate Similarity	NPD7983	Approved
0.7158	Intermediate Similarity	NPD5363	Approved
0.7053	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4270	Approved
0.7021	Intermediate Similarity	NPD5209	Approved
0.7021	Intermediate Similarity	NPD4269	Approved
0.699	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4252	Approved
0.697	Remote Similarity	NPD6698	Approved
0.697	Remote Similarity	NPD46	Approved
0.697	Remote Similarity	NPD7838	Discovery
0.6961	Remote Similarity	NPD7839	Suspended
0.6947	Remote Similarity	NPD7154	Phase 3
0.6907	Remote Similarity	NPD5786	Approved
0.6848	Remote Similarity	NPD4756	Discovery
0.6832	Remote Similarity	NPD5779	Approved
0.6832	Remote Similarity	NPD5778	Approved
0.6809	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6686	Approved
0.6771	Remote Similarity	NPD5362	Discontinued
0.6737	Remote Similarity	NPD5369	Approved
0.67	Remote Similarity	NPD5370	Suspended
0.6699	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6628	Remote Similarity	NPD3197	Phase 1
0.6607	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4268	Approved
0.6596	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4271	Approved
0.6591	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7637	Suspended
0.6569	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6101	Approved
0.6466	Remote Similarity	NPD7115	Discovery
0.646	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4822	Approved
0.6458	Remote Similarity	NPD4821	Approved
0.6458	Remote Similarity	NPD4819	Approved
0.6458	Remote Similarity	NPD4820	Approved
0.6429	Remote Similarity	NPD5332	Approved
0.6429	Remote Similarity	NPD6110	Phase 1
0.6429	Remote Similarity	NPD5331	Approved
0.6417	Remote Similarity	NPD7830	Approved
0.6417	Remote Similarity	NPD7829	Approved
0.6408	Remote Similarity	NPD6411	Approved
0.6392	Remote Similarity	NPD4790	Discontinued
0.6387	Remote Similarity	NPD8444	Approved
0.6337	Remote Similarity	NPD4250	Approved
0.6337	Remote Similarity	NPD4251	Approved
0.6327	Remote Similarity	NPD6435	Approved
0.6321	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD8039	Approved
0.6273	Remote Similarity	NPD6647	Phase 2
0.6238	Remote Similarity	NPD4249	Approved
0.6186	Remote Similarity	NPD7500	Approved
0.6167	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7642	Approved
0.6147	Remote Similarity	NPD7639	Approved
0.6147	Remote Similarity	NPD7640	Approved
0.6134	Remote Similarity	NPD7641	Discontinued
0.6132	Remote Similarity	NPD5282	Discontinued
0.6129	Remote Similarity	NPD8074	Phase 3
0.6122	Remote Similarity	NPD5368	Approved
0.6091	Remote Similarity	NPD5344	Discontinued
0.6055	Remote Similarity	NPD7638	Approved
0.6048	Remote Similarity	NPD8451	Approved
0.6047	Remote Similarity	NPD6109	Phase 1
0.6032	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD969	Suspended
0.598	Remote Similarity	NPD1694	Approved
0.5968	Remote Similarity	NPD8341	Approved
0.5968	Remote Similarity	NPD8342	Approved
0.5968	Remote Similarity	NPD8299	Approved
0.5968	Remote Similarity	NPD8340	Approved
0.5965	Remote Similarity	NPD6412	Phase 2
0.5963	Remote Similarity	NPD6083	Phase 2
0.5963	Remote Similarity	NPD6084	Phase 2
0.5954	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD2067	Discontinued
0.5935	Remote Similarity	NPD7623	Phase 3
0.5935	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD8080	Discontinued
0.5934	Remote Similarity	NPD3704	Approved
0.5922	Remote Similarity	NPD5279	Phase 3
0.592	Remote Similarity	NPD7507	Approved
0.5917	Remote Similarity	NPD7505	Discontinued
0.5897	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD8328	Phase 3
0.5859	Remote Similarity	NPD8390	Approved
0.5859	Remote Similarity	NPD8392	Approved
0.5859	Remote Similarity	NPD8391	Approved
0.5854	Remote Similarity	NPD7503	Approved
0.5847	Remote Similarity	NPD6882	Approved
0.5827	Remote Similarity	NPD7736	Approved
0.5825	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD1696	Phase 3
0.581	Remote Similarity	NPD5737	Approved
0.581	Remote Similarity	NPD6672	Approved
0.5806	Remote Similarity	NPD6370	Approved
0.5794	Remote Similarity	NPD8273	Phase 1
0.578	Remote Similarity	NPD5695	Phase 3
0.5778	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6881	Approved
0.5776	Remote Similarity	NPD6899	Approved
0.5763	Remote Similarity	NPD2204	Approved
0.5761	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD689	Discontinued
0.5755	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD7747	Phase 1
0.5748	Remote Similarity	NPD7746	Phase 1
0.5748	Remote Similarity	NPD8293	Discontinued
0.5741	Remote Similarity	NPD6399	Phase 3
0.5739	Remote Similarity	NPD6675	Approved
0.5739	Remote Similarity	NPD5739	Approved
0.5739	Remote Similarity	NPD7128	Approved
0.5739	Remote Similarity	NPD6402	Approved
0.5738	Remote Similarity	NPD7327	Approved
0.5738	Remote Similarity	NPD7328	Approved
0.5727	Remote Similarity	NPD4228	Discovery
0.5726	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8033	Approved
0.5714	Remote Similarity	NPD8297	Approved
0.5714	Remote Similarity	NPD7492	Approved
0.5714	Remote Similarity	NPD6053	Discontinued
0.5702	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD2629	Approved
0.5692	Remote Similarity	NPD7260	Phase 2
0.5691	Remote Similarity	NPD7516	Approved
0.569	Remote Similarity	NPD5697	Approved
0.5688	Remote Similarity	NPD7748	Approved
0.5682	Remote Similarity	NPD9119	Approved
0.5682	Remote Similarity	NPD69	Approved
0.5678	Remote Similarity	NPD7102	Approved
0.5678	Remote Similarity	NPD6883	Approved
0.5678	Remote Similarity	NPD7290	Approved
0.5669	Remote Similarity	NPD6616	Approved
0.5648	Remote Similarity	NPD5694	Approved
0.5648	Remote Similarity	NPD5693	Phase 1
0.5648	Remote Similarity	NPD6050	Approved
0.5648	Remote Similarity	NPD7515	Phase 2
0.5645	Remote Similarity	NPD6319	Approved
0.5645	Remote Similarity	NPD8377	Approved
0.5645	Remote Similarity	NPD8294	Approved
0.5645	Remote Similarity	NPD6054	Approved
0.5641	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6011	Approved
0.5641	Remote Similarity	NPD7320	Approved
0.563	Remote Similarity	NPD8130	Phase 1
0.563	Remote Similarity	NPD6869	Approved
0.563	Remote Similarity	NPD6649	Approved
0.563	Remote Similarity	NPD6847	Approved
0.563	Remote Similarity	NPD6617	Approved
0.563	Remote Similarity	NPD6650	Approved
0.5625	Remote Similarity	NPD5696	Approved
0.5625	Remote Similarity	NPD7078	Approved
0.5625	Remote Similarity	NPD9495	Approved
0.5619	Remote Similarity	NPD5330	Approved
0.5619	Remote Similarity	NPD6684	Approved
0.5619	Remote Similarity	NPD7334	Approved
0.5619	Remote Similarity	NPD6422	Discontinued
0.5619	Remote Similarity	NPD7521	Approved
0.5619	Remote Similarity	NPD7146	Approved
0.5619	Remote Similarity	NPD6409	Approved
0.5614	Remote Similarity	NPD7632	Discontinued
0.5603	Remote Similarity	NPD4211	Phase 1
0.56	Remote Similarity	NPD8380	Approved
0.56	Remote Similarity	NPD3732	Approved
0.56	Remote Similarity	NPD8379	Approved
0.56	Remote Similarity	NPD8378	Approved
0.56	Remote Similarity	NPD8296	Approved
0.56	Remote Similarity	NPD8335	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