NPASS Compound

Structure

NPC261184 OpenBabel07101719252D 31 35 0 0 1 0 0 0 0 0999 V2000 -0.2007 -1.6451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6369 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9692 0.2463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3590 2.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0818 1.4749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3217 1.7730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7922 -1.7645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4784 1.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5978 2.1660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6569 0.7082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9990 -0.0449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1852 -2.6841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6426 3.1650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6479 0.5740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3920 -0.9644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 30 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 15 27 1 0 0 0 0 16 28 2 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 29 1 6 0 0 0 19 24 1 0 0 0 0 19 25 1 6 0 0 0 20 26 1 6 0 0 0 20 27 1 0 0 0 0 21 25 1 6 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 0 0 0 0 23 27 1 1 0 0 0 23 31 1 0 0 0 0 25 4 1 6 0 0 0 26 5 1 6 0 0 0 27 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.29
Volume:	460.017
LogP:	5.682
LogD:	4.523
LogS:	-5.294
# Rotatable Bonds:	2
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	4.914
Fsp3:	0.815
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.854
MDCK Permeability:	2.207906982221175e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.133
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.931
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.345
Plasma Protein Binding (PPB):	90.45194244384766%
Volume Distribution (VD):	1.827
Pgp-substrate:	7.040512561798096%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.114
CYP2C19-substrate:	0.804
CYP2C9-inhibitor:	0.387
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.196
CYP3A4-inhibitor:	0.673
CYP3A4-substrate:	0.591

ADMET: Excretion

Clearance (CL):	8.629
Half-life (T1/2):	0.076

ADMET: Toxicity

hERG Blockers:	0.388
Human Hepatotoxicity (H-HT):	0.255
Drug-inuced Liver Injury (DILI):	0.269
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.131
Carcinogencity:	0.443
Eye Corrosion:	0.413
Eye Irritation:	0.412
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC261184

Natural Product ID:	NPC261184
*Common Name:**	Salmahyrtisol A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HTVZLAVMRJYGFM-XOLBZSSLSA-N
Standard InCHI:	InChI=1S/C27H40O4/c1-16(28)31-23-22-17(9-13-30-22)18(29)14-20-26(5)12-8-19-24(2,3)10-7-11-25(19,4)21(26)15-27(20,23)6/h9,13,18-21,23,29H,7-8,10-12,14-15H2,1-6H3/t18-,19-,20-,21+,23+,25-,26-,27-/m0/s1
SMILES:	CC(=O)O[C@@H]1c2c(cco2)[C@H](C[C@H]2[C@]3(C)CC[C@H]4C(C)(C)CCC[C@]4(C)[C@H]3C[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458031
PubChem CID:	637424
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002936] Cycloheptafurans

*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
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[11809054]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[16124771]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[16378375]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584401]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Maldives	n.a.	PMID[9873492]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>=	1.0	ug.mL-1	PMID[544881]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>=	1.0	ug.mL-1	PMID[544881]
NPT81	Cell Line	A549	Homo sapiens	IC50	>=	1.0	ug.mL-1	PMID[544881]

☑ 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 NPC261184 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	344
0.1-0.2	1266
0.2-0.3	2668
0.3-0.4	5412
0.4-0.5	11422
0.5-0.6	8990
0.6-0.7	8921
0.7-0.8	3261
0.8-0.85	345
0.85-0.9	64
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9739	High Similarity	NPC116639
0.8805	High Similarity	NPC75310
0.8758	High Similarity	NPC474611
0.8726	High Similarity	NPC472654
0.872	High Similarity	NPC475779
0.8712	High Similarity	NPC88841
0.8712	High Similarity	NPC288602
0.8704	High Similarity	NPC470789
0.8693	High Similarity	NPC205765
0.8679	High Similarity	NPC246164
0.8679	High Similarity	NPC475777
0.8659	High Similarity	NPC123088
0.865	High Similarity	NPC193798
0.865	High Similarity	NPC5079
0.865	High Similarity	NPC188649
0.8642	High Similarity	NPC84349
0.8642	High Similarity	NPC477403
0.8631	High Similarity	NPC471437
0.8625	High Similarity	NPC114880
0.8614	High Similarity	NPC296558
0.8608	High Similarity	NPC211625
0.8599	High Similarity	NPC250228
0.8598	High Similarity	NPC234660
0.8598	High Similarity	NPC51568
0.8598	High Similarity	NPC663
0.8598	High Similarity	NPC224394
0.8589	High Similarity	NPC477402
0.8589	High Similarity	NPC25255
0.8589	High Similarity	NPC335761
0.858	High Similarity	NPC45101
0.858	High Similarity	NPC194499
0.8571	High Similarity	NPC472785
0.8563	High Similarity	NPC470995
0.8562	High Similarity	NPC121615
0.8562	High Similarity	NPC294511
0.8554	High Similarity	NPC472784
0.8554	High Similarity	NPC478179
0.8554	High Similarity	NPC476850
0.8554	High Similarity	NPC472651
0.8554	High Similarity	NPC476853
0.8554	High Similarity	NPC473753
0.8554	High Similarity	NPC473766
0.8554	High Similarity	NPC476861
0.8545	High Similarity	NPC476857
0.8545	High Similarity	NPC476858
0.8545	High Similarity	NPC476856
0.8537	High Similarity	NPC69028
0.8537	High Similarity	NPC82851
0.8537	High Similarity	NPC18986
0.8537	High Similarity	NPC329938
0.8528	High Similarity	NPC475967
0.8519	High Similarity	NPC469485
0.8512	High Similarity	NPC159232
0.8512	High Similarity	NPC475641
0.8512	High Similarity	NPC285227
0.8512	High Similarity	NPC475237
0.8503	High Similarity	NPC472652
0.8494	Intermediate Similarity	NPC478178
0.8494	Intermediate Similarity	NPC121995
0.8494	Intermediate Similarity	NPC214600
0.8494	Intermediate Similarity	NPC149945
0.8494	Intermediate Similarity	NPC23387
0.8491	Intermediate Similarity	NPC195325
0.8485	Intermediate Similarity	NPC472783
0.8485	Intermediate Similarity	NPC134254
0.8485	Intermediate Similarity	NPC472780
0.8485	Intermediate Similarity	NPC39986
0.8485	Intermediate Similarity	NPC283209
0.8485	Intermediate Similarity	NPC302369
0.8485	Intermediate Similarity	NPC477405
0.8476	Intermediate Similarity	NPC472653
0.8476	Intermediate Similarity	NPC287559
0.8466	Intermediate Similarity	NPC304692
0.8466	Intermediate Similarity	NPC261597
0.8466	Intermediate Similarity	NPC88007
0.8466	Intermediate Similarity	NPC195954
0.8466	Intermediate Similarity	NPC173544
0.8466	Intermediate Similarity	NPC249021
0.8457	Intermediate Similarity	NPC44675
0.8457	Intermediate Similarity	NPC214541
0.8457	Intermediate Similarity	NPC281258
0.8457	Intermediate Similarity	NPC35000
0.8452	Intermediate Similarity	NPC302392
0.8447	Intermediate Similarity	NPC44577
0.8447	Intermediate Similarity	NPC33938
0.8447	Intermediate Similarity	NPC75906
0.8443	Intermediate Similarity	NPC472774
0.8443	Intermediate Similarity	NPC472775
0.8443	Intermediate Similarity	NPC472764
0.8438	Intermediate Similarity	NPC212257
0.8438	Intermediate Similarity	NPC156189
0.8434	Intermediate Similarity	NPC476860
0.8434	Intermediate Similarity	NPC276551
0.8434	Intermediate Similarity	NPC470940
0.8424	Intermediate Similarity	NPC263432
0.8424	Intermediate Similarity	NPC472767
0.8424	Intermediate Similarity	NPC472771
0.8424	Intermediate Similarity	NPC472781
0.8424	Intermediate Similarity	NPC68848
0.8424	Intermediate Similarity	NPC117986
0.8424	Intermediate Similarity	NPC472782
0.8421	Intermediate Similarity	NPC478177
0.8418	Intermediate Similarity	NPC62799
0.8415	Intermediate Similarity	NPC237155
0.8415	Intermediate Similarity	NPC473368
0.8415	Intermediate Similarity	NPC472779
0.8415	Intermediate Similarity	NPC475226
0.8412	Intermediate Similarity	NPC471632
0.8412	Intermediate Similarity	NPC236004
0.8408	Intermediate Similarity	NPC137295
0.8408	Intermediate Similarity	NPC476944
0.8405	Intermediate Similarity	NPC104736
0.8405	Intermediate Similarity	NPC107646
0.8405	Intermediate Similarity	NPC126723
0.8405	Intermediate Similarity	NPC41880
0.8405	Intermediate Similarity	NPC263265
0.8405	Intermediate Similarity	NPC209364
0.8395	Intermediate Similarity	NPC178932
0.8395	Intermediate Similarity	NPC30222
0.8393	Intermediate Similarity	NPC472765
0.8393	Intermediate Similarity	NPC271235
0.8393	Intermediate Similarity	NPC472766
0.8385	Intermediate Similarity	NPC472787
0.8383	Intermediate Similarity	NPC470875
0.8373	Intermediate Similarity	NPC285567
0.8373	Intermediate Similarity	NPC469338
0.8373	Intermediate Similarity	NPC472773
0.8373	Intermediate Similarity	NPC292389
0.8365	Intermediate Similarity	NPC216755
0.8365	Intermediate Similarity	NPC471174
0.8365	Intermediate Similarity	NPC71821
0.8364	Intermediate Similarity	NPC191828
0.8363	Intermediate Similarity	NPC167340
0.8354	Intermediate Similarity	NPC472778
0.8354	Intermediate Similarity	NPC472772
0.8354	Intermediate Similarity	NPC472777
0.8354	Intermediate Similarity	NPC472776
0.8354	Intermediate Similarity	NPC286722
0.8354	Intermediate Similarity	NPC36655
0.8354	Intermediate Similarity	NPC472283
0.8344	Intermediate Similarity	NPC64568
0.8344	Intermediate Similarity	NPC296807
0.8344	Intermediate Similarity	NPC155939
0.8344	Intermediate Similarity	NPC469336
0.8344	Intermediate Similarity	NPC267632
0.8344	Intermediate Similarity	NPC141538
0.8344	Intermediate Similarity	NPC92979
0.8343	Intermediate Similarity	NPC472659
0.8343	Intermediate Similarity	NPC118086
0.8333	Intermediate Similarity	NPC474219
0.8333	Intermediate Similarity	NPC469503
0.8333	Intermediate Similarity	NPC270312
0.8333	Intermediate Similarity	NPC476224
0.8333	Intermediate Similarity	NPC472282
0.8333	Intermediate Similarity	NPC474378
0.8323	Intermediate Similarity	NPC107571
0.8323	Intermediate Similarity	NPC56358
0.8323	Intermediate Similarity	NPC46551
0.8323	Intermediate Similarity	NPC90953
0.8323	Intermediate Similarity	NPC228842
0.8323	Intermediate Similarity	NPC470997
0.8323	Intermediate Similarity	NPC469849
0.8314	Intermediate Similarity	NPC472665
0.8313	Intermediate Similarity	NPC200782
0.8313	Intermediate Similarity	NPC207978
0.8313	Intermediate Similarity	NPC96443
0.8313	Intermediate Similarity	NPC93666
0.8313	Intermediate Similarity	NPC6326
0.8313	Intermediate Similarity	NPC290400
0.8313	Intermediate Similarity	NPC197596
0.8313	Intermediate Similarity	NPC470792
0.8313	Intermediate Similarity	NPC472668
0.8313	Intermediate Similarity	NPC19747
0.8313	Intermediate Similarity	NPC79571
0.8304	Intermediate Similarity	NPC94763
0.8304	Intermediate Similarity	NPC469576
0.8303	Intermediate Similarity	NPC262872
0.8303	Intermediate Similarity	NPC473473
0.8303	Intermediate Similarity	NPC307383
0.8303	Intermediate Similarity	NPC140952
0.8303	Intermediate Similarity	NPC475295
0.8303	Intermediate Similarity	NPC472823
0.8293	Intermediate Similarity	NPC60973
0.8291	Intermediate Similarity	NPC84479
0.8284	Intermediate Similarity	NPC471397
0.8282	Intermediate Similarity	NPC282445
0.8272	Intermediate Similarity	NPC272590
0.8272	Intermediate Similarity	NPC18135
0.8269	Intermediate Similarity	NPC282973
0.8269	Intermediate Similarity	NPC148374
0.8263	Intermediate Similarity	NPC476035
0.8263	Intermediate Similarity	NPC475039
0.8263	Intermediate Similarity	NPC165218
0.8263	Intermediate Similarity	NPC14499
0.8263	Intermediate Similarity	NPC472669
0.8261	Intermediate Similarity	NPC125182
0.8261	Intermediate Similarity	NPC234494
0.8261	Intermediate Similarity	NPC470791
0.8261	Intermediate Similarity	NPC69647
0.8261	Intermediate Similarity	NPC470790

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 NPC261184 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	798
0.2-0.3	1708
0.3-0.4	2599
0.4-0.5	2263
0.5-0.6	1068
0.6-0.7	349
0.7-0.8	49
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8457	Intermediate Similarity	NPD5760	Phase 2
0.8457	Intermediate Similarity	NPD5761	Phase 2
0.8333	Intermediate Similarity	NPD8434	Phase 2
0.8256	Intermediate Similarity	NPD6764	Approved
0.8256	Intermediate Similarity	NPD6765	Approved
0.8253	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD6784	Approved
0.8068	Intermediate Similarity	NPD6785	Approved
0.7937	Intermediate Similarity	NPD4628	Phase 3
0.7831	Intermediate Similarity	NPD6599	Discontinued
0.7798	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7075	Discontinued
0.7633	Intermediate Similarity	NPD6801	Discontinued
0.7576	Intermediate Similarity	NPD6799	Approved
0.7531	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6559	Discontinued
0.7442	Intermediate Similarity	NPD5402	Approved
0.744	Intermediate Similarity	NPD5403	Approved
0.744	Intermediate Similarity	NPD920	Approved
0.7425	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5762	Approved
0.7423	Intermediate Similarity	NPD5763	Approved
0.7416	Intermediate Similarity	NPD7799	Discontinued
0.7414	Intermediate Similarity	NPD919	Approved
0.741	Intermediate Similarity	NPD7236	Approved
0.7399	Intermediate Similarity	NPD3882	Suspended
0.7384	Intermediate Similarity	NPD7819	Suspended
0.7381	Intermediate Similarity	NPD6273	Approved
0.7377	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8127	Discontinued
0.7329	Intermediate Similarity	NPD6355	Discontinued
0.7321	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5401	Approved
0.7317	Intermediate Similarity	NPD6002	Phase 3
0.7317	Intermediate Similarity	NPD6004	Phase 3
0.7317	Intermediate Similarity	NPD1471	Phase 3
0.7317	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6005	Phase 3
0.7317	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2799	Discontinued
0.7278	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD3749	Approved
0.7256	Intermediate Similarity	NPD1551	Phase 2
0.7251	Intermediate Similarity	NPD3226	Approved
0.725	Intermediate Similarity	NPD8404	Phase 2
0.7241	Intermediate Similarity	NPD3817	Phase 2
0.7232	Intermediate Similarity	NPD1247	Approved
0.7229	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2533	Approved
0.7219	Intermediate Similarity	NPD2532	Approved
0.7219	Intermediate Similarity	NPD2534	Approved
0.7215	Intermediate Similarity	NPD5647	Approved
0.7215	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4380	Phase 2
0.7202	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7033	Discontinued
0.7193	Intermediate Similarity	NPD7239	Suspended
0.7182	Intermediate Similarity	NPD5844	Phase 1
0.7175	Intermediate Similarity	NPD5494	Approved
0.7174	Intermediate Similarity	NPD8313	Approved
0.7174	Intermediate Similarity	NPD8312	Approved
0.7168	Intermediate Similarity	NPD7411	Suspended
0.7167	Intermediate Similarity	NPD7473	Discontinued
0.7159	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7458	Discontinued
0.7151	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD3818	Discontinued
0.7126	Intermediate Similarity	NPD2800	Approved
0.7108	Intermediate Similarity	NPD2346	Discontinued
0.7108	Intermediate Similarity	NPD2344	Approved
0.7086	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1549	Phase 2
0.7059	Intermediate Similarity	NPD8150	Discontinued
0.7052	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2796	Approved
0.7039	Intermediate Similarity	NPD7199	Phase 2
0.7037	Intermediate Similarity	NPD2313	Discontinued
0.7033	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1934	Approved
0.7027	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1243	Approved
0.7019	Intermediate Similarity	NPD6832	Phase 2
0.7017	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6166	Phase 2
0.7011	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4967	Phase 2
0.7006	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7768	Phase 2
0.7006	Intermediate Similarity	NPD4965	Approved
0.7006	Intermediate Similarity	NPD4966	Approved
0.7	Intermediate Similarity	NPD6232	Discontinued
0.6982	Remote Similarity	NPD3750	Approved
0.6973	Remote Similarity	NPD7685	Pre-registration
0.6973	Remote Similarity	NPD7251	Discontinued
0.697	Remote Similarity	NPD6653	Approved
0.6964	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1608	Approved
0.6961	Remote Similarity	NPD3926	Phase 2
0.6951	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2935	Discontinued
0.6946	Remote Similarity	NPD6099	Approved
0.6946	Remote Similarity	NPD6100	Approved
0.6941	Remote Similarity	NPD3887	Approved
0.6941	Remote Similarity	NPD2309	Approved
0.694	Remote Similarity	NPD3751	Discontinued
0.6937	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7808	Phase 3
0.6933	Remote Similarity	NPD3268	Approved
0.6933	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD37	Approved
0.6923	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6797	Phase 2
0.6909	Remote Similarity	NPD447	Suspended
0.6906	Remote Similarity	NPD7315	Approved
0.6904	Remote Similarity	NPD7435	Discontinued
0.6893	Remote Similarity	NPD2801	Approved
0.689	Remote Similarity	NPD8032	Phase 2
0.689	Remote Similarity	NPD6233	Phase 2
0.6886	Remote Similarity	NPD1510	Phase 2
0.6882	Remote Similarity	NPD4110	Phase 3
0.6882	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1607	Approved
0.6865	Remote Similarity	NPD7074	Phase 3
0.6862	Remote Similarity	NPD8407	Phase 2
0.686	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD9717	Approved
0.6851	Remote Similarity	NPD6959	Discontinued
0.6848	Remote Similarity	NPD1240	Approved
0.6848	Remote Similarity	NPD4140	Approved
0.6842	Remote Similarity	NPD2354	Approved
0.6833	Remote Similarity	NPD6234	Discontinued
0.6832	Remote Similarity	NPD1203	Approved
0.6832	Remote Similarity	NPD2797	Approved
0.6829	Remote Similarity	NPD6798	Discontinued
0.6829	Remote Similarity	NPD3764	Approved
0.6821	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7058	Phase 2
0.6816	Remote Similarity	NPD7057	Phase 3
0.6813	Remote Similarity	NPD3787	Discontinued
0.6811	Remote Similarity	NPD7286	Phase 2
0.6811	Remote Similarity	NPD7054	Approved
0.6795	Remote Similarity	NPD9092	Discovery
0.6791	Remote Similarity	NPD8368	Discontinued
0.6786	Remote Similarity	NPD4308	Phase 3
0.6786	Remote Similarity	NPD3748	Approved
0.6784	Remote Similarity	NPD7003	Approved
0.6782	Remote Similarity	NPD1512	Approved
0.6774	Remote Similarity	NPD7472	Approved
0.6772	Remote Similarity	NPD17	Approved
0.677	Remote Similarity	NPD1876	Approved
0.6769	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7095	Approved
0.6765	Remote Similarity	NPD4534	Discontinued
0.6765	Remote Similarity	NPD5958	Discontinued
0.6757	Remote Similarity	NPD7228	Approved
0.675	Remote Similarity	NPD3972	Approved
0.6747	Remote Similarity	NPD4060	Phase 1
0.6744	Remote Similarity	NPD6190	Approved
0.6743	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5953	Discontinued
0.6734	Remote Similarity	NPD7497	Discontinued
0.6728	Remote Similarity	NPD6362	Approved
0.6727	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7028	Phase 2
0.6721	Remote Similarity	NPD5711	Approved
0.6721	Remote Similarity	NPD6808	Phase 2
0.6721	Remote Similarity	NPD7229	Phase 3
0.6721	Remote Similarity	NPD5710	Approved
0.6719	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5735	Approved
0.6707	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD2353	Approved
0.6706	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7874	Approved
0.67	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4062	Phase 3
0.6687	Remote Similarity	NPD6663	Approved
0.6687	Remote Similarity	NPD2798	Approved
0.6683	Remote Similarity	NPD3057	Approved
0.6667	Remote Similarity	NPD6777	Approved
0.6667	Remote Similarity	NPD6781	Approved
0.6667	Remote Similarity	NPD6780	Approved
0.6667	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4107	Approved
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD6651	Approved
0.6667	Remote Similarity	NPD6776	Approved
0.6667	Remote Similarity	NPD6782	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