NPASS Compound

Structure

NPC275837 OpenBabel07101719132D 37 38 0 0 1 0 0 0 0 0999 V2000 -1.5731 -0.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5696 7.5264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1225 5.7333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6378 8.0440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3282 8.3029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 4.9568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3108 8.4923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1566 5.4744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4836 5.9227 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 6.6298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0179 9.1994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 4.5085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5731 3.9392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2588 -0.9659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1895 6.3710 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3449 8.7511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0353 7.5958 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 -2.4495 6.1815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 4.6980 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 33 1 0 0 0 0 8 34 1 0 0 0 0 9 17 2 0 0 0 0 9 18 1 0 0 0 0 10 17 1 0 0 0 0 10 23 1 0 0 0 0 11 18 2 0 0 0 0 11 20 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 13 37 1 0 0 0 0 14 1 1 1 0 0 0 14 35 1 0 0 0 0 15 26 2 0 0 0 0 15 33 1 0 0 0 0 16 27 2 0 0 0 0 16 36 1 0 0 0 0 17 24 1 0 0 0 0 18 28 1 0 0 0 0 19 37 1 6 0 0 0 20 24 2 0 0 0 0 20 29 1 0 0 0 0 21 24 1 0 0 0 0 21 30 2 0 0 0 0 22 13 1 1 0 0 0 22 25 1 0 0 0 0 22 36 1 0 0 0 0 23 31 2 0 0 0 0 23 35 1 0 0 0 0 25 32 2 0 0 0 0 25 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.17
Volume:	517.953
LogP:	2.986
LogD:	2.388
LogS:	-3.947
# Rotatable Bonds:	11
TPSA:	162.73
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.282
Synthetic Accessibility Score:	4.635
Fsp3:	0.56
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.194
MDCK Permeability:	5.989932833472267e-05
Pgp-inhibitor:	0.052
Pgp-substrate:	0.058
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	56.56453323364258%
Volume Distribution (VD):	0.4
Pgp-substrate:	54.384368896484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.23
CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.457
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.477
CYP2C9-substrate:	0.832
CYP2D6-inhibitor:	0.523
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.704
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	9.604
Half-life (T1/2):	0.942

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.81
Skin Sensitization:	0.897
Carcinogencity:	0.258
Eye Corrosion:	0.295
Eye Irritation:	0.249
Respiratory Toxicity:	0.107

Download Data

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

Natural Product: NPC275837

Natural Product ID:	NPC275837
*Common Name:**	Sumalarin B
IUPAC Name:	2-acetyloxyethyl (2S)-2-acetyloxy-3-[[(5S,9S)-13,15-dihydroxy-5-methyl-3,11-dioxo-4-oxabicyclo[10.4.0]hexadeca-1(12),13,15-trien-9-yl]sulfanyl]propanoate
Synonyms:
Standard InCHIKey:	QDQXSVXGAZHQLE-OSGPJOMKSA-N
Standard InCHI:	InChI=1S/C25H32O11S/c1-14-5-4-6-19(37-13-22(36-16(3)27)25(32)34-8-7-33-15(2)26)12-21(30)24-17(10-23(31)35-14)9-18(28)11-20(24)29/h9,11,14,19,22,28-29H,4-8,10,12-13H2,1-3H3/t14-,19-,22+/m0/s1
SMILES:	CC(=O)O[C@@H](C(=O)OCCOC(=O)C)CS[C@H]1CCC[C@H](C)OC(=O)Cc2c(C(=O)C1)c(O)cc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3087768
PubChem CID:	72945490
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO33114	penicillium sumatrense ma-92	Species	Aspergillaceae	Eukaryota	rhizosphere of the mangrove Lumnitzera racemosa	n.a.	n.a.	PMID[24195466]

☑ 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	7

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1312	Cell Line	SW1990	Homo sapiens	IC50	=	11000.0	nM	PMID[557973]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	7000.0	nM	PMID[557973]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	8000.0	nM	PMID[557973]
NPT1229	Cell Line	Huh-7	Homo sapiens	IC50	=	5500.0	nM	PMID[557973]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4700.0	nM	PMID[557973]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	4600.0	nM	PMID[557973]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6800.0	nM	PMID[557973]

☑ 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 NPC275837 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	332
0.1-0.2	1486
0.2-0.3	3939
0.3-0.4	9595
0.4-0.5	10078
0.5-0.6	5595
0.6-0.7	8018
0.7-0.8	3500
0.8-0.85	138
0.85-0.9	13
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.973	High Similarity	NPC55092
0.9662	High Similarity	NPC213224
0.8926	High Similarity	NPC354984
0.8904	High Similarity	NPC474771
0.8904	High Similarity	NPC65837
0.8904	High Similarity	NPC149372
0.8904	High Similarity	NPC474849
0.8904	High Similarity	NPC178467
0.8844	High Similarity	NPC475974
0.8716	High Similarity	NPC472403
0.8716	High Similarity	NPC9121
0.8716	High Similarity	NPC177307
0.8667	High Similarity	NPC313123
0.8667	High Similarity	NPC478217
0.8658	High Similarity	NPC474655
0.8591	High Similarity	NPC191835
0.8553	High Similarity	NPC478202
0.8543	High Similarity	NPC472035
0.8543	High Similarity	NPC478201
0.8543	High Similarity	NPC244923
0.8523	High Similarity	NPC71256
0.8523	High Similarity	NPC70380
0.8467	Intermediate Similarity	NPC212693
0.8467	Intermediate Similarity	NPC33144
0.8467	Intermediate Similarity	NPC478200
0.8467	Intermediate Similarity	NPC94248
0.8411	Intermediate Similarity	NPC52358
0.8408	Intermediate Similarity	NPC56204
0.8377	Intermediate Similarity	NPC126882
0.8377	Intermediate Similarity	NPC478203
0.8377	Intermediate Similarity	NPC210966
0.8355	Intermediate Similarity	NPC158472
0.8344	Intermediate Similarity	NPC472602
0.8333	Intermediate Similarity	NPC210320
0.8323	Intermediate Similarity	NPC257558
0.8323	Intermediate Similarity	NPC472034
0.8313	Intermediate Similarity	NPC478221
0.8312	Intermediate Similarity	NPC472006
0.8302	Intermediate Similarity	NPC478224
0.8301	Intermediate Similarity	NPC53649
0.8301	Intermediate Similarity	NPC472603
0.8301	Intermediate Similarity	NPC67650
0.8301	Intermediate Similarity	NPC1704
0.8299	Intermediate Similarity	NPC17840
0.8299	Intermediate Similarity	NPC247477
0.8293	Intermediate Similarity	NPC34910
0.8293	Intermediate Similarity	NPC477677
0.8293	Intermediate Similarity	NPC264756
0.8291	Intermediate Similarity	NPC472891
0.8289	Intermediate Similarity	NPC139634
0.8289	Intermediate Similarity	NPC105456
0.8288	Intermediate Similarity	NPC41263
0.828	Intermediate Similarity	NPC73411
0.828	Intermediate Similarity	NPC215711
0.8278	Intermediate Similarity	NPC194579
0.8269	Intermediate Similarity	NPC472033
0.8269	Intermediate Similarity	NPC473023
0.8255	Intermediate Similarity	NPC153783
0.825	Intermediate Similarity	NPC137301
0.825	Intermediate Similarity	NPC478231
0.8235	Intermediate Similarity	NPC472600
0.8235	Intermediate Similarity	NPC472601
0.8217	Intermediate Similarity	NPC472036
0.8217	Intermediate Similarity	NPC14098
0.8212	Intermediate Similarity	NPC235115
0.821	Intermediate Similarity	NPC472889
0.8205	Intermediate Similarity	NPC83272
0.8199	Intermediate Similarity	NPC478230
0.8199	Intermediate Similarity	NPC317585
0.8199	Intermediate Similarity	NPC472890
0.8199	Intermediate Similarity	NPC69043
0.8199	Intermediate Similarity	NPC208173
0.8199	Intermediate Similarity	NPC170189
0.8199	Intermediate Similarity	NPC99381
0.8194	Intermediate Similarity	NPC159721
0.8194	Intermediate Similarity	NPC51106
0.8187	Intermediate Similarity	NPC115249
0.8187	Intermediate Similarity	NPC76041
0.8187	Intermediate Similarity	NPC184284
0.8182	Intermediate Similarity	NPC472604
0.8182	Intermediate Similarity	NPC158634
0.8182	Intermediate Similarity	NPC472605
0.8176	Intermediate Similarity	NPC164762
0.8176	Intermediate Similarity	NPC60413
0.817	Intermediate Similarity	NPC268052
0.817	Intermediate Similarity	NPC32360
0.817	Intermediate Similarity	NPC92655
0.8165	Intermediate Similarity	NPC240253
0.8165	Intermediate Similarity	NPC240622
0.8165	Intermediate Similarity	NPC471642
0.8165	Intermediate Similarity	NPC221352
0.8165	Intermediate Similarity	NPC471641
0.8153	Intermediate Similarity	NPC107625
0.8151	Intermediate Similarity	NPC473691
0.8141	Intermediate Similarity	NPC151607
0.8141	Intermediate Similarity	NPC42540
0.8141	Intermediate Similarity	NPC277426
0.8141	Intermediate Similarity	NPC210425
0.8141	Intermediate Similarity	NPC86373
0.8141	Intermediate Similarity	NPC280404
0.8137	Intermediate Similarity	NPC472211
0.8133	Intermediate Similarity	NPC48036
0.8133	Intermediate Similarity	NPC37299
0.8133	Intermediate Similarity	NPC180261
0.8129	Intermediate Similarity	NPC474385
0.8125	Intermediate Similarity	NPC215921
0.8125	Intermediate Similarity	NPC200773
0.8125	Intermediate Similarity	NPC240768
0.8125	Intermediate Similarity	NPC91809
0.8125	Intermediate Similarity	NPC70016
0.8121	Intermediate Similarity	NPC219892
0.8121	Intermediate Similarity	NPC189823
0.8113	Intermediate Similarity	NPC84142
0.8113	Intermediate Similarity	NPC6923
0.811	Intermediate Similarity	NPC284918
0.8098	Intermediate Similarity	NPC246466
0.8098	Intermediate Similarity	NPC478225
0.8098	Intermediate Similarity	NPC478226
0.8089	Intermediate Similarity	NPC312789
0.8082	Intermediate Similarity	NPC201728
0.8082	Intermediate Similarity	NPC262671
0.8082	Intermediate Similarity	NPC477454
0.8077	Intermediate Similarity	NPC472610
0.8077	Intermediate Similarity	NPC469542
0.8077	Intermediate Similarity	NPC471731
0.8065	Intermediate Similarity	NPC37530
0.8065	Intermediate Similarity	NPC475730
0.8063	Intermediate Similarity	NPC475407
0.8063	Intermediate Similarity	NPC469619
0.8063	Intermediate Similarity	NPC469670
0.8052	Intermediate Similarity	NPC88269
0.8052	Intermediate Similarity	NPC247409
0.8039	Intermediate Similarity	NPC135837
0.8026	Intermediate Similarity	NPC278375
0.8026	Intermediate Similarity	NPC27407
0.8013	Intermediate Similarity	NPC82913
0.8013	Intermediate Similarity	NPC43627
0.8013	Intermediate Similarity	NPC469579
0.8013	Intermediate Similarity	NPC471733
0.8012	Intermediate Similarity	NPC205918
0.8	Intermediate Similarity	NPC44378
0.8	Intermediate Similarity	NPC99441
0.8	Intermediate Similarity	NPC243701
0.8	Intermediate Similarity	NPC4423
0.8	Intermediate Similarity	NPC280753
0.8	Intermediate Similarity	NPC476684
0.8	Intermediate Similarity	NPC155205
0.8	Intermediate Similarity	NPC77325
0.8	Intermediate Similarity	NPC198249
0.8	Intermediate Similarity	NPC198927
0.8	Intermediate Similarity	NPC120171
0.7987	Intermediate Similarity	NPC166583
0.7987	Intermediate Similarity	NPC53362
0.7975	Intermediate Similarity	NPC79998
0.7975	Intermediate Similarity	NPC473692
0.7974	Intermediate Similarity	NPC158481
0.7962	Intermediate Similarity	NPC471643
0.7962	Intermediate Similarity	NPC471639
0.7961	Intermediate Similarity	NPC175943
0.7961	Intermediate Similarity	NPC474097
0.7961	Intermediate Similarity	NPC474519
0.7961	Intermediate Similarity	NPC474394
0.7952	Intermediate Similarity	NPC317544
0.7947	Intermediate Similarity	NPC478190
0.7947	Intermediate Similarity	NPC476389
0.7937	Intermediate Similarity	NPC94781
0.7937	Intermediate Similarity	NPC153417
0.7935	Intermediate Similarity	NPC162939
0.7935	Intermediate Similarity	NPC275356
0.7933	Intermediate Similarity	NPC259942
0.7927	Intermediate Similarity	NPC472050
0.7925	Intermediate Similarity	NPC237208
0.7925	Intermediate Similarity	NPC51513
0.7925	Intermediate Similarity	NPC202112
0.7914	Intermediate Similarity	NPC471695
0.7908	Intermediate Similarity	NPC290803
0.7908	Intermediate Similarity	NPC180905
0.7908	Intermediate Similarity	NPC182496
0.7908	Intermediate Similarity	NPC142027
0.7898	Intermediate Similarity	NPC471644
0.7898	Intermediate Similarity	NPC250755
0.7898	Intermediate Similarity	NPC471640
0.7892	Intermediate Similarity	NPC472055
0.7888	Intermediate Similarity	NPC270160
0.7888	Intermediate Similarity	NPC237440
0.7885	Intermediate Similarity	NPC64664
0.7879	Intermediate Similarity	NPC473395
0.7879	Intermediate Similarity	NPC257309
0.7875	Intermediate Similarity	NPC471734
0.7871	Intermediate Similarity	NPC221104
0.787	Intermediate Similarity	NPC20237
0.7867	Intermediate Similarity	NPC92624
0.7866	Intermediate Similarity	NPC82592
0.7866	Intermediate Similarity	NPC471456
0.7866	Intermediate Similarity	NPC16082
0.7862	Intermediate Similarity	NPC29577
0.7862	Intermediate Similarity	NPC134621
0.7857	Intermediate Similarity	NPC474726
0.7857	Intermediate Similarity	NPC50455
0.7857	Intermediate Similarity	NPC249181

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 NPC275837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	902
0.2-0.3	1977
0.3-0.4	2822
0.4-0.5	1919
0.5-0.6	933
0.6-0.7	263
0.7-0.8	49
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
0.7879	Intermediate Similarity	NPD7075	Discontinued
0.7821	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7819	Suspended
0.764	Intermediate Similarity	NPD2533	Approved
0.764	Intermediate Similarity	NPD2532	Approved
0.764	Intermediate Similarity	NPD2534	Approved
0.7586	Intermediate Similarity	NPD5953	Discontinued
0.7582	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6799	Approved
0.7545	Intermediate Similarity	NPD3817	Phase 2
0.753	Intermediate Similarity	NPD6801	Discontinued
0.7516	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.7471	Intermediate Similarity	NPD7286	Phase 2
0.7457	Intermediate Similarity	NPD7473	Discontinued
0.744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3882	Suspended
0.7384	Intermediate Similarity	NPD6232	Discontinued
0.7365	Intermediate Similarity	NPD7411	Suspended
0.7362	Intermediate Similarity	NPD7390	Discontinued
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7321	Intermediate Similarity	NPD1934	Approved
0.7317	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4380	Phase 2
0.7299	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6166	Phase 2
0.7299	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD943	Approved
0.7247	Intermediate Similarity	NPD7251	Discontinued
0.7235	Intermediate Similarity	NPD5402	Approved
0.7229	Intermediate Similarity	NPD5403	Approved
0.7225	Intermediate Similarity	NPD6959	Discontinued
0.7207	Intermediate Similarity	NPD7808	Phase 3
0.7207	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6797	Phase 2
0.7188	Intermediate Similarity	NPD1510	Phase 2
0.7184	Intermediate Similarity	NPD7229	Phase 3
0.7174	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1549	Phase 2
0.7152	Intermediate Similarity	NPD1240	Approved
0.7151	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7074	Phase 3
0.7108	Intermediate Similarity	NPD5401	Approved
0.7079	Intermediate Similarity	NPD7054	Approved
0.7076	Intermediate Similarity	NPD2801	Approved
0.7073	Intermediate Similarity	NPD3750	Approved
0.7066	Intermediate Similarity	NPD1512	Approved
0.7063	Intermediate Similarity	NPD1607	Approved
0.7049	Intermediate Similarity	NPD8150	Discontinued
0.7039	Intermediate Similarity	NPD7472	Approved
0.7037	Intermediate Similarity	NPD5404	Approved
0.7037	Intermediate Similarity	NPD5408	Approved
0.7037	Intermediate Similarity	NPD5405	Approved
0.7037	Intermediate Similarity	NPD5406	Approved
0.7037	Intermediate Similarity	NPD2796	Approved
0.703	Intermediate Similarity	NPD6190	Approved
0.7022	Intermediate Similarity	NPD3818	Discontinued
0.7012	Intermediate Similarity	NPD1652	Phase 2
0.7011	Intermediate Similarity	NPD919	Approved
0.7	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7768	Phase 2
0.6989	Remote Similarity	NPD5711	Approved
0.6989	Remote Similarity	NPD5710	Approved
0.6983	Remote Similarity	NPD5844	Phase 1
0.6981	Remote Similarity	NPD4248	Discontinued
0.697	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6651	Approved
0.6954	Remote Similarity	NPD3749	Approved
0.6954	Remote Similarity	NPD9545	Approved
0.6948	Remote Similarity	NPD9269	Phase 2
0.6946	Remote Similarity	NPD1511	Approved
0.6941	Remote Similarity	NPD3226	Approved
0.6933	Remote Similarity	NPD2935	Discontinued
0.6918	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD9268	Approved
0.6905	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1201	Approved
0.6879	Remote Similarity	NPD1465	Phase 2
0.6868	Remote Similarity	NPD6559	Discontinued
0.6867	Remote Similarity	NPD4628	Phase 3
0.6854	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD1247	Approved
0.6829	Remote Similarity	NPD1551	Phase 2
0.6821	Remote Similarity	NPD9493	Approved
0.6815	Remote Similarity	NPD1470	Approved
0.6807	Remote Similarity	NPD2800	Approved
0.6804	Remote Similarity	NPD7435	Discontinued
0.679	Remote Similarity	NPD4340	Discontinued
0.678	Remote Similarity	NPD5494	Approved
0.6769	Remote Similarity	NPD8319	Approved
0.6769	Remote Similarity	NPD8320	Phase 1
0.6768	Remote Similarity	NPD3748	Approved
0.6766	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5049	Phase 3
0.676	Remote Similarity	NPD3926	Phase 2
0.6727	Remote Similarity	NPD6100	Approved
0.6727	Remote Similarity	NPD6099	Approved
0.6725	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD37	Approved
0.6723	Remote Similarity	NPD6234	Discontinued
0.6711	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD1164	Approved
0.6708	Remote Similarity	NPD3764	Approved
0.6707	Remote Similarity	NPD1243	Approved
0.6706	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4965	Approved
0.6705	Remote Similarity	NPD4967	Phase 2
0.6705	Remote Similarity	NPD4966	Approved
0.6702	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6355	Discontinued
0.6685	Remote Similarity	NPD6764	Approved
0.6685	Remote Similarity	NPD6765	Approved
0.6684	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD6971	Discontinued
0.6649	Remote Similarity	NPD6534	Approved
0.6649	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6535	Approved
0.6648	Remote Similarity	NPD3751	Discontinued
0.6648	Remote Similarity	NPD7199	Phase 2
0.6633	Remote Similarity	NPD8151	Discontinued
0.6632	Remote Similarity	NPD7700	Phase 2
0.6632	Remote Similarity	NPD7699	Phase 2
0.6631	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2403	Approved
0.6628	Remote Similarity	NPD920	Approved
0.6626	Remote Similarity	NPD4060	Phase 1
0.6622	Remote Similarity	NPD74	Approved
0.6622	Remote Similarity	NPD9266	Approved
0.6613	Remote Similarity	NPD8312	Approved
0.6613	Remote Similarity	NPD8313	Approved
0.6611	Remote Similarity	NPD3787	Discontinued
0.6607	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7874	Approved
0.66	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3300	Phase 2
0.6588	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7440	Discontinued
0.6585	Remote Similarity	NPD447	Suspended
0.6584	Remote Similarity	NPD6832	Phase 2
0.6581	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2799	Discontinued
0.6564	Remote Similarity	NPD6781	Approved
0.6564	Remote Similarity	NPD6776	Approved
0.6564	Remote Similarity	NPD6777	Approved
0.6564	Remote Similarity	NPD6778	Approved
0.6564	Remote Similarity	NPD6779	Approved
0.6564	Remote Similarity	NPD6663	Approved
0.6564	Remote Similarity	NPD6780	Approved
0.6564	Remote Similarity	NPD6782	Approved
0.6562	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6085	Phase 2
0.6557	Remote Similarity	NPD7228	Approved
0.6554	Remote Similarity	NPD9263	Approved
0.6554	Remote Similarity	NPD9267	Approved
0.6554	Remote Similarity	NPD9264	Approved
0.6554	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7696	Phase 3
0.6548	Remote Similarity	NPD7680	Approved
0.6548	Remote Similarity	NPD7698	Approved
0.6548	Remote Similarity	NPD7697	Approved
0.6538	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD2531	Phase 2
0.6522	Remote Similarity	NPD5736	Approved
0.6519	Remote Similarity	NPD9717	Approved
0.6515	Remote Similarity	NPD7871	Phase 2
0.6515	Remote Similarity	NPD7870	Phase 2
0.6512	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2654	Approved
0.6503	Remote Similarity	NPD6798	Discontinued
0.6503	Remote Similarity	NPD3268	Approved
0.6488	Remote Similarity	NPD2346	Discontinued
0.6471	Remote Similarity	NPD8166	Discontinued
0.6467	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4062	Phase 3
0.6461	Remote Similarity	NPD5353	Approved
0.6457	Remote Similarity	NPD7458	Discontinued
0.6453	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD468	Phase 1
0.6424	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD7701	Phase 2
0.6416	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD411	Approved
0.6398	Remote Similarity	NPD1203	Approved
0.6391	Remote Similarity	NPD5763	Approved
0.6391	Remote Similarity	NPD1471	Phase 3
0.6391	Remote Similarity	NPD7266	Discontinued
0.6391	Remote Similarity	NPD5762	Approved
0.6391	Remote Similarity	NPD2344	Approved
0.6387	Remote Similarity	NPD6841	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