NPASS Compound

Structure

NPC36754 OpenBabel07101719132D 43 49 0 0 1 0 0 0 0 0999 V2000 3.2270 1.2030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1915 0.4950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6903 4.8787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2869 3.8482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1523 4.6563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7721 5.2904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2007 4.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5980 0.7403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9204 1.8461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7869 3.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3046 2.5777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4160 4.0575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8869 1.0283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2672 1.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1915 1.4950 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0417 3.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5095 2.8733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4755 3.7100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4773 4.3348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5960 3.2673 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2825 2.6348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0242 1.6179 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2299 2.9570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1004 2.6348 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5998 0.8001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8364 3.1501 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1033 2.4700 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9164 2.3230 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8627 2.6462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8215 3.7273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9463 0.3232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4232 3.9381 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4626 1.8461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9314 1.3231 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4566 3.5167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5024 4.1123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6033 4.3508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7640 -0.2524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4676 4.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8175 2.9569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1575 3.6018 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8578 2.9191 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 8 14 2 0 0 0 0 9 15 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 11 23 1 0 0 0 0 12 26 1 0 0 0 0 12 32 1 0 0 0 0 15 33 1 1 0 0 0 16 20 1 0 0 0 0 16 30 1 0 0 0 0 17 21 2 0 0 0 0 17 28 1 0 0 0 0 18 35 2 0 0 0 0 18 40 1 0 0 0 0 19 36 2 0 0 0 0 19 41 1 0 0 0 0 20 10 1 1 0 0 0 20 24 1 0 0 0 0 21 33 1 0 0 0 0 22 25 1 0 0 0 0 22 34 1 1 0 0 0 23 27 1 0 0 0 0 23 32 1 1 0 0 0 24 9 1 6 0 0 0 24 42 1 0 0 0 0 25 8 1 6 0 0 0 25 43 1 0 0 0 0 26 27 1 0 0 0 0 26 40 1 6 0 0 0 27 14 1 6 0 0 0 28 29 1 0 0 0 0 28 34 1 6 0 0 0 29 33 1 1 0 0 0 29 41 1 0 0 0 0 30 37 2 0 0 0 0 30 42 1 0 0 0 0 31 34 1 0 0 0 0 31 38 2 0 0 0 0 31 43 1 0 0 0 0 32 7 1 1 0 0 0 32 39 1 0 0 0 0 33 13 1 6 0 0 0 34 13 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.28
Volume:	597.382
LogP:	3.722
LogD:	2.682
LogS:	-4.474
# Rotatable Bonds:	4
TPSA:	125.43
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.219
Synthetic Accessibility Score:	7.331
Fsp3:	0.706
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.395
MDCK Permeability:	9.868675988400355e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.922
Human Intestinal Absorption (HIA):	0.661
20% Bioavailability (F20%):	0.896
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	72.62226104736328%
Volume Distribution (VD):	2.178
Pgp-substrate:	9.565084457397461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.468
CYP2C9-inhibitor:	0.274
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.648
CYP3A4-substrate:	0.586

ADMET: Excretion

Clearance (CL):	3.01
Half-life (T1/2):	0.064

ADMET: Toxicity

hERG Blockers:	0.258
Human Hepatotoxicity (H-HT):	0.408
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.811
Maximum Recommended Daily Dose:	0.16
Skin Sensitization:	0.889
Carcinogencity:	0.145
Eye Corrosion:	0.011
Eye Irritation:	0.023
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC36754

Natural Product ID:	NPC36754
*Common Name:**	FKBQSBKDOZCOOM-VTVCHGPLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FKBQSBKDOZCOOM-VTVCHGPLSA-N
Standard InCHI:	InChI=1S/C34H42O9/c1-14-8-25-22(11-23-27(14)26(40-18(5)35)12-32(23,7)39)34(31(38)43-25)13-33-15(2)9-24-20(16(3)30(37)42-24)10-21(33)17(4)28(34)29(33)41-19(6)36/h8,15,20,22-29,39H,3,9-13H2,1-2,4-7H3/t15-,20+,22-,23+,24-,25-,26-,27+,28-,29-,32+,33-,34-/m0/s1
SMILES:	CC(=O)O[C@H]1[C@@H]2C(=C3[C@]1(C[C@]12C(=O)O[C@@H]2[C@@H]1C[C@@H]1[C@@H](C(=C2)C)[C@H](C[C@@]1(C)O)OC(=O)C)[C@@H](C)C[C@H]1[C@H](C3)C(=C)C(=O)O1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2426511
PubChem CID:	73352328
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO32526	lineariifolia turcz	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24044895]

☑ 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
NPT2257	Cell Line	MCF-10A	Homo sapiens	IC50	>	50000.0	nM	PMID[554340]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	10700.0	nM	PMID[554340]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3400.0	nM	PMID[554340]

☑ 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 NPC36754 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	295
0.1-0.2	1909
0.2-0.3	6638
0.3-0.4	15697
0.4-0.5	9454
0.5-0.6	6397
0.6-0.7	1994
0.7-0.8	275
0.8-0.85	22
0.85-0.9	12
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC161060
0.945	High Similarity	NPC471382
0.9099	High Similarity	NPC471380
0.8909	High Similarity	NPC471884
0.8839	High Similarity	NPC209058
0.8716	High Similarity	NPC475217
0.8716	High Similarity	NPC252234
0.8596	High Similarity	NPC123117
0.8584	High Similarity	NPC23967
0.8571	High Similarity	NPC48305
0.8571	High Similarity	NPC474923
0.8482	Intermediate Similarity	NPC475588
0.8318	Intermediate Similarity	NPC213078
0.8241	Intermediate Similarity	NPC161493
0.8224	Intermediate Similarity	NPC67584
0.8182	Intermediate Similarity	NPC129992
0.8136	Intermediate Similarity	NPC475238
0.8131	Intermediate Similarity	NPC127019
0.8067	Intermediate Similarity	NPC475372
0.8056	Intermediate Similarity	NPC213698
0.8056	Intermediate Similarity	NPC52044
0.8036	Intermediate Similarity	NPC474775
0.8	Intermediate Similarity	NPC312536
0.8	Intermediate Similarity	NPC221615
0.7983	Intermediate Similarity	NPC475323
0.7982	Intermediate Similarity	NPC24956
0.7982	Intermediate Similarity	NPC18019
0.7967	Intermediate Similarity	NPC144625
0.7963	Intermediate Similarity	NPC470010
0.7963	Intermediate Similarity	NPC262133
0.7963	Intermediate Similarity	NPC470013
0.7963	Intermediate Similarity	NPC198853
0.7963	Intermediate Similarity	NPC323008
0.7963	Intermediate Similarity	NPC477131
0.7944	Intermediate Similarity	NPC133698
0.7931	Intermediate Similarity	NPC477103
0.792	Intermediate Similarity	NPC172823
0.7917	Intermediate Similarity	NPC288679
0.7895	Intermediate Similarity	NPC223450
0.789	Intermediate Similarity	NPC170120
0.7886	Intermediate Similarity	NPC42747
0.7863	Intermediate Similarity	NPC287311
0.7857	Intermediate Similarity	NPC171759
0.7857	Intermediate Similarity	NPC13071
0.785	Intermediate Similarity	NPC301969
0.785	Intermediate Similarity	NPC37607
0.7845	Intermediate Similarity	NPC477102
0.7833	Intermediate Similarity	NPC473656
0.7826	Intermediate Similarity	NPC26617
0.7805	Intermediate Similarity	NPC192309
0.7798	Intermediate Similarity	NPC90453
0.7788	Intermediate Similarity	NPC86077
0.7787	Intermediate Similarity	NPC143755
0.7778	Intermediate Similarity	NPC29821
0.7778	Intermediate Similarity	NPC63193
0.7778	Intermediate Similarity	NPC293001
0.7778	Intermediate Similarity	NPC57304
0.7778	Intermediate Similarity	NPC290651
0.7778	Intermediate Similarity	NPC171360
0.7778	Intermediate Similarity	NPC131209
0.7778	Intermediate Similarity	NPC133888
0.7778	Intermediate Similarity	NPC35959
0.7768	Intermediate Similarity	NPC280963
0.7757	Intermediate Similarity	NPC283409
0.775	Intermediate Similarity	NPC277583
0.7748	Intermediate Similarity	NPC108475
0.7748	Intermediate Similarity	NPC170143
0.7748	Intermediate Similarity	NPC213947
0.7742	Intermediate Similarity	NPC469352
0.7742	Intermediate Similarity	NPC1538
0.7739	Intermediate Similarity	NPC243998
0.7739	Intermediate Similarity	NPC54737
0.7731	Intermediate Similarity	NPC9848
0.7731	Intermediate Similarity	NPC474937
0.7731	Intermediate Similarity	NPC312017
0.7727	Intermediate Similarity	NPC476053
0.7727	Intermediate Similarity	NPC37408
0.7727	Intermediate Similarity	NPC163228
0.7719	Intermediate Similarity	NPC124881
0.7717	Intermediate Similarity	NPC475371
0.7712	Intermediate Similarity	NPC474750
0.7706	Intermediate Similarity	NPC135776
0.7705	Intermediate Similarity	NPC469380
0.7705	Intermediate Similarity	NPC472667
0.7699	Intermediate Similarity	NPC150923
0.7699	Intermediate Similarity	NPC477950
0.7692	Intermediate Similarity	NPC59489
0.7692	Intermediate Similarity	NPC139838
0.7685	Intermediate Similarity	NPC216284
0.7685	Intermediate Similarity	NPC54065
0.7685	Intermediate Similarity	NPC297474
0.7685	Intermediate Similarity	NPC35809
0.7674	Intermediate Similarity	NPC224623
0.7664	Intermediate Similarity	NPC471149
0.7664	Intermediate Similarity	NPC91248
0.7664	Intermediate Similarity	NPC79549
0.7658	Intermediate Similarity	NPC142529
0.7658	Intermediate Similarity	NPC91771
0.7656	Intermediate Similarity	NPC469351
0.7647	Intermediate Similarity	NPC101825
0.7647	Intermediate Similarity	NPC89227
0.7647	Intermediate Similarity	NPC475391
0.7647	Intermediate Similarity	NPC265499
0.7647	Intermediate Similarity	NPC126691
0.7647	Intermediate Similarity	NPC151216
0.7647	Intermediate Similarity	NPC17138
0.7647	Intermediate Similarity	NPC221511
0.7647	Intermediate Similarity	NPC170212
0.7647	Intermediate Similarity	NPC215643
0.7642	Intermediate Similarity	NPC474585
0.7642	Intermediate Similarity	NPC4548
0.7632	Intermediate Similarity	NPC475320
0.7627	Intermediate Similarity	NPC257240
0.7615	Intermediate Similarity	NPC221282
0.7615	Intermediate Similarity	NPC155215
0.7611	Intermediate Similarity	NPC241221
0.7611	Intermediate Similarity	NPC186861
0.7607	Intermediate Similarity	NPC308191
0.7603	Intermediate Similarity	NPC148458
0.7593	Intermediate Similarity	NPC155935
0.7593	Intermediate Similarity	NPC215556
0.7589	Intermediate Similarity	NPC471150
0.7586	Intermediate Similarity	NPC190867
0.7586	Intermediate Similarity	NPC179891
0.7586	Intermediate Similarity	NPC291643
0.7583	Intermediate Similarity	NPC473535
0.757	Intermediate Similarity	NPC24728
0.7568	Intermediate Similarity	NPC472873
0.7568	Intermediate Similarity	NPC304886
0.7563	Intermediate Similarity	NPC174471
0.7563	Intermediate Similarity	NPC474871
0.7563	Intermediate Similarity	NPC260786
0.7563	Intermediate Similarity	NPC96739
0.7561	Intermediate Similarity	NPC5292
0.7559	Intermediate Similarity	NPC11732
0.7545	Intermediate Similarity	NPC153590
0.7545	Intermediate Similarity	NPC258216
0.7545	Intermediate Similarity	NPC473234
0.7545	Intermediate Similarity	NPC308656
0.7545	Intermediate Similarity	NPC60386
0.7545	Intermediate Similarity	NPC473263
0.7545	Intermediate Similarity	NPC476300
0.7545	Intermediate Similarity	NPC473273
0.7544	Intermediate Similarity	NPC475099
0.7541	Intermediate Similarity	NPC475305
0.7541	Intermediate Similarity	NPC239273
0.7521	Intermediate Similarity	NPC473911
0.7521	Intermediate Similarity	NPC90472
0.7521	Intermediate Similarity	NPC138303
0.7521	Intermediate Similarity	NPC133677
0.7521	Intermediate Similarity	NPC474872
0.7521	Intermediate Similarity	NPC67290
0.75	Intermediate Similarity	NPC221144
0.75	Intermediate Similarity	NPC19336
0.75	Intermediate Similarity	NPC100487
0.75	Intermediate Similarity	NPC189338
0.75	Intermediate Similarity	NPC95290
0.75	Intermediate Similarity	NPC178875
0.75	Intermediate Similarity	NPC473577
0.75	Intermediate Similarity	NPC203659
0.75	Intermediate Similarity	NPC100267
0.75	Intermediate Similarity	NPC76550
0.75	Intermediate Similarity	NPC475524
0.75	Intermediate Similarity	NPC123855
0.75	Intermediate Similarity	NPC474550
0.75	Intermediate Similarity	NPC126156
0.75	Intermediate Similarity	NPC185876
0.75	Intermediate Similarity	NPC475585
0.748	Intermediate Similarity	NPC153440
0.748	Intermediate Similarity	NPC475401
0.7479	Intermediate Similarity	NPC238850
0.7478	Intermediate Similarity	NPC78127
0.7478	Intermediate Similarity	NPC471757
0.7477	Intermediate Similarity	NPC67493
0.746	Intermediate Similarity	NPC469382
0.7456	Intermediate Similarity	NPC70865
0.7456	Intermediate Similarity	NPC471381
0.7455	Intermediate Similarity	NPC191339
0.7455	Intermediate Similarity	NPC475925
0.7455	Intermediate Similarity	NPC286341
0.7442	Intermediate Similarity	NPC470851
0.744	Intermediate Similarity	NPC52839
0.7438	Intermediate Similarity	NPC46269
0.7438	Intermediate Similarity	NPC71889
0.7438	Intermediate Similarity	NPC106395
0.7436	Intermediate Similarity	NPC475290
0.7434	Intermediate Similarity	NPC477949
0.7431	Intermediate Similarity	NPC4986
0.7431	Intermediate Similarity	NPC32922
0.7431	Intermediate Similarity	NPC472872
0.7419	Intermediate Similarity	NPC180640
0.7419	Intermediate Similarity	NPC477092
0.7414	Intermediate Similarity	NPC110989
0.7414	Intermediate Similarity	NPC475321
0.7411	Intermediate Similarity	NPC36954
0.7411	Intermediate Similarity	NPC224689
0.7407	Intermediate Similarity	NPC118601
0.7405	Intermediate Similarity	NPC469674
0.7402	Intermediate Similarity	NPC469379
0.7402	Intermediate Similarity	NPC75856

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 NPC36754 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	2542
0.2-0.3	4026
0.3-0.4	1631
0.4-0.5	380
0.5-0.6	240
0.6-0.7	27
0.7-0.8	3
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
0.7826	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD6053	Discontinued
0.7627	Intermediate Similarity	NPD6371	Approved
0.7431	Intermediate Similarity	NPD1695	Approved
0.7257	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6008	Approved
0.6947	Remote Similarity	NPD7507	Approved
0.6885	Remote Similarity	NPD7320	Approved
0.6855	Remote Similarity	NPD6649	Approved
0.6855	Remote Similarity	NPD6650	Approved
0.6829	Remote Similarity	NPD6373	Approved
0.6829	Remote Similarity	NPD6372	Approved
0.68	Remote Similarity	NPD8297	Approved
0.6791	Remote Similarity	NPD7319	Approved
0.6786	Remote Similarity	NPD4251	Approved
0.6786	Remote Similarity	NPD4250	Approved
0.678	Remote Similarity	NPD7638	Approved
0.6767	Remote Similarity	NPD7078	Approved
0.6757	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5785	Approved
0.6748	Remote Similarity	NPD6881	Approved
0.6748	Remote Similarity	NPD6899	Approved
0.6727	Remote Similarity	NPD5362	Discontinued
0.6723	Remote Similarity	NPD7639	Approved
0.6723	Remote Similarity	NPD7640	Approved
0.6721	Remote Similarity	NPD6402	Approved
0.6721	Remote Similarity	NPD7128	Approved
0.6721	Remote Similarity	NPD5739	Approved
0.6721	Remote Similarity	NPD6675	Approved
0.672	Remote Similarity	NPD8130	Phase 1
0.6696	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6641	Remote Similarity	NPD8033	Approved
0.664	Remote Similarity	NPD7102	Approved
0.664	Remote Similarity	NPD6883	Approved
0.664	Remote Similarity	NPD7290	Approved
0.6638	Remote Similarity	NPD6399	Phase 3
0.6636	Remote Similarity	NPD6435	Approved
0.6617	Remote Similarity	NPD7492	Approved
0.6613	Remote Similarity	NPD6686	Approved
0.6593	Remote Similarity	NPD7736	Approved
0.6587	Remote Similarity	NPD6847	Approved
0.6587	Remote Similarity	NPD6617	Approved
0.6587	Remote Similarity	NPD6869	Approved
0.6567	Remote Similarity	NPD6616	Approved
0.6565	Remote Similarity	NPD6054	Approved
0.6565	Remote Similarity	NPD6319	Approved
0.656	Remote Similarity	NPD6013	Approved
0.656	Remote Similarity	NPD6014	Approved
0.656	Remote Similarity	NPD6012	Approved
0.6555	Remote Similarity	NPD6084	Phase 2
0.6555	Remote Similarity	NPD6083	Phase 2
0.6532	Remote Similarity	NPD5701	Approved
0.6525	Remote Similarity	NPD5695	Phase 3
0.6519	Remote Similarity	NPD8293	Discontinued
0.65	Remote Similarity	NPD5696	Approved
0.6484	Remote Similarity	NPD4632	Approved
0.648	Remote Similarity	NPD6011	Approved
0.6466	Remote Similarity	NPD6698	Approved
0.6466	Remote Similarity	NPD6370	Approved
0.6466	Remote Similarity	NPD46	Approved
0.6462	Remote Similarity	NPD7115	Discovery
0.646	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4822	Approved
0.6455	Remote Similarity	NPD4821	Approved
0.6455	Remote Similarity	NPD4819	Approved
0.6455	Remote Similarity	NPD4820	Approved
0.6455	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5368	Approved
0.6441	Remote Similarity	NPD5282	Discontinued
0.6439	Remote Similarity	NPD8377	Approved
0.6439	Remote Similarity	NPD6059	Approved
0.6439	Remote Similarity	NPD8294	Approved
0.6435	Remote Similarity	NPD6903	Approved
0.6429	Remote Similarity	NPD7154	Phase 3
0.6412	Remote Similarity	NPD7328	Approved
0.6412	Remote Similarity	NPD7327	Approved
0.641	Remote Similarity	NPD7983	Approved
0.6404	Remote Similarity	NPD5786	Approved
0.6396	Remote Similarity	NPD4790	Discontinued
0.6391	Remote Similarity	NPD8380	Approved
0.6391	Remote Similarity	NPD6015	Approved
0.6391	Remote Similarity	NPD8379	Approved
0.6391	Remote Similarity	NPD8378	Approved
0.6391	Remote Similarity	NPD6016	Approved
0.6391	Remote Similarity	NPD8335	Approved
0.6391	Remote Similarity	NPD8296	Approved
0.6387	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7516	Approved
0.6343	Remote Similarity	NPD5988	Approved
0.6341	Remote Similarity	NPD5211	Phase 2
0.6336	Remote Similarity	NPD6009	Approved
0.6331	Remote Similarity	NPD7260	Phase 2
0.6328	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD7838	Discovery
0.6316	Remote Similarity	NPD5363	Approved
0.6311	Remote Similarity	NPD5285	Approved
0.6311	Remote Similarity	NPD4696	Approved
0.6311	Remote Similarity	NPD5286	Approved
0.6296	Remote Similarity	NPD7604	Phase 2
0.6286	Remote Similarity	NPD6845	Suspended
0.6283	Remote Similarity	NPD5331	Approved
0.6283	Remote Similarity	NPD5332	Approved
0.6281	Remote Similarity	NPD4755	Approved
0.6273	Remote Similarity	NPD4268	Approved
0.6273	Remote Similarity	NPD4271	Approved
0.6271	Remote Similarity	NPD5284	Approved
0.6271	Remote Similarity	NPD5281	Approved
0.6271	Remote Similarity	NPD5693	Phase 1
0.627	Remote Similarity	NPD6412	Phase 2
0.6269	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5983	Phase 2
0.6269	Remote Similarity	NPD7503	Approved
0.6261	Remote Similarity	NPD7146	Approved
0.6261	Remote Similarity	NPD7521	Approved
0.6261	Remote Similarity	NPD5330	Approved
0.6261	Remote Similarity	NPD7334	Approved
0.6261	Remote Similarity	NPD6684	Approved
0.6261	Remote Similarity	NPD6409	Approved
0.626	Remote Similarity	NPD6274	Approved
0.625	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5369	Approved
0.6241	Remote Similarity	NPD7101	Approved
0.6241	Remote Similarity	NPD7100	Approved
0.624	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.624	Remote Similarity	NPD5141	Approved
0.624	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6051	Approved
0.6231	Remote Similarity	NPD8133	Approved
0.623	Remote Similarity	NPD4225	Approved
0.6218	Remote Similarity	NPD5778	Approved
0.6218	Remote Similarity	NPD5779	Approved
0.621	Remote Similarity	NPD5225	Approved
0.621	Remote Similarity	NPD5224	Approved
0.621	Remote Similarity	NPD7632	Discontinued
0.621	Remote Similarity	NPD4633	Approved
0.621	Remote Similarity	NPD5226	Approved
0.6204	Remote Similarity	NPD6336	Discontinued
0.6202	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4269	Approved
0.6195	Remote Similarity	NPD4270	Approved
0.6186	Remote Similarity	NPD5207	Approved
0.6179	Remote Similarity	NPD4700	Approved
0.6165	Remote Similarity	NPD6335	Approved
0.616	Remote Similarity	NPD5175	Approved
0.616	Remote Similarity	NPD5174	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD8515	Approved
0.6148	Remote Similarity	NPD8513	Phase 3
0.6148	Remote Similarity	NPD8517	Approved
0.6148	Remote Similarity	NPD8516	Approved
0.6134	Remote Similarity	NPD8035	Phase 2
0.6134	Remote Similarity	NPD7637	Suspended
0.6134	Remote Similarity	NPD8034	Phase 2
0.6129	Remote Similarity	NPD5223	Approved
0.6129	Remote Similarity	NPD1700	Approved
0.6126	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD4634	Approved
0.6116	Remote Similarity	NPD5210	Approved
0.6116	Remote Similarity	NPD4629	Approved
0.6102	Remote Similarity	NPD6904	Approved
0.6102	Remote Similarity	NPD4753	Phase 2
0.6102	Remote Similarity	NPD6080	Approved
0.6102	Remote Similarity	NPD6673	Approved
0.6098	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD4729	Approved
0.6094	Remote Similarity	NPD4730	Approved
0.609	Remote Similarity	NPD6317	Approved
0.6063	Remote Similarity	NPD4767	Approved
0.6063	Remote Similarity	NPD4768	Approved
0.6047	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD6313	Approved
0.6045	Remote Similarity	NPD6314	Approved
0.6034	Remote Similarity	NPD1694	Approved
0.6033	Remote Similarity	NPD6001	Approved
0.6029	Remote Similarity	NPD6908	Approved
0.6029	Remote Similarity	NPD6909	Approved
0.6018	Remote Similarity	NPD4252	Approved
0.6017	Remote Similarity	NPD6672	Approved
0.6017	Remote Similarity	NPD5737	Approved
0.6016	Remote Similarity	NPD7902	Approved
0.6016	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD5251	Approved
0.6	Remote Similarity	NPD5250	Approved
0.6	Remote Similarity	NPD5249	Phase 3
0.6	Remote Similarity	NPD6033	Approved
0.6	Remote Similarity	NPD5248	Approved
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD5247	Approved
0.6	Remote Similarity	NPD6411	Approved
0.5983	Remote Similarity	NPD6098	Approved
0.5969	Remote Similarity	NPD5128	Approved
0.5969	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD5328	Approved
0.595	Remote Similarity	NPD4202	Approved
0.5948	Remote Similarity	NPD3666	Approved
0.5948	Remote Similarity	NPD3133	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