NPASS Compound

Structure

NPC471382 OpenBabel07101719252D 40 46 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 0.4540 2.3261 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 2.4160 4.0575 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 -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 2 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 -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 -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 1.4232 3.9381 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 1.2299 2.9570 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 0.7430 4.6712 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 -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 3.8175 2.9569 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 2 14 1 0 0 0 0 3 15 2 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 19 1 0 0 0 0 10 23 1 0 0 0 0 10 24 1 0 0 0 0 11 20 1 0 0 0 0 11 30 1 0 0 0 0 13 1 1 6 0 0 0 13 25 1 0 0 0 0 14 31 1 1 0 0 0 15 18 1 0 0 0 0 15 28 1 0 0 0 0 16 19 2 0 0 0 0 16 26 1 0 0 0 0 17 33 2 0 0 0 0 17 38 1 0 0 0 0 18 9 1 1 0 0 0 18 21 1 0 0 0 0 19 31 1 0 0 0 0 20 22 1 0 0 0 0 20 32 1 1 0 0 0 21 8 1 6 0 0 0 21 39 1 0 0 0 0 22 7 1 6 0 0 0 22 40 1 0 0 0 0 23 25 1 0 0 0 0 23 38 1 6 0 0 0 24 30 1 1 0 0 0 24 34 1 0 0 0 0 25 30 1 1 0 0 0 26 27 1 0 0 0 0 26 32 1 6 0 0 0 27 31 1 1 0 0 0 27 35 1 0 0 0 0 28 36 2 0 0 0 0 28 39 1 0 0 0 0 29 32 1 0 0 0 0 29 37 2 0 0 0 0 29 40 1 0 0 0 0 30 6 1 1 0 0 0 31 12 1 6 0 0 0 32 12 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	554.29
Volume:	559.272
LogP:	3.679
LogD:	3.215
LogS:	-4.586
# Rotatable Bonds:	2
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.219
Synthetic Accessibility Score:	7.348
Fsp3:	0.781
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:	-5.47
MDCK Permeability:	8.283253555418923e-05
Pgp-inhibitor:	0.893
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.208
20% Bioavailability (F20%):	0.369
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.228
Plasma Protein Binding (PPB):	77.2863998413086%
Volume Distribution (VD):	1.368
Pgp-substrate:	13.265562057495117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.604
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.718
CYP3A4-substrate:	0.558

ADMET: Excretion

Clearance (CL):	13.735
Half-life (T1/2):	0.127

ADMET: Toxicity

hERG Blockers:	0.916
Human Hepatotoxicity (H-HT):	0.296
Drug-inuced Liver Injury (DILI):	0.876
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.928
Carcinogencity:	0.624
Eye Corrosion:	0.012
Eye Irritation:	0.016
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC471382

Natural Product ID:	NPC471382
*Common Name:**	OJVIJEPDCXTKTE-HPSPMMRGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OJVIJEPDCXTKTE-HPSPMMRGSA-N
Standard InCHI:	InChI=1S/C32H42O8/c1-13-7-22-20(11-30(6)24(34)10-23(25(13)30)38-17(5)33)32(29(37)40-22)12-31-14(2)8-21-18(15(3)28(36)39-21)9-19(31)16(4)26(32)27(31)35/h13-14,18,20-27,34-35H,3,7-12H2,1-2,4-6H3/t13-,14+,18-,20+,21+,22+,23+,24+,25-,26+,27+,30-,31+,32+/m1/s1
SMILES:	CC1CC2C(CC3(C1C(CC3O)OC(=O)C)C)C4(CC56C(CC7C(CC5=C(C4C6O)C)C(=C)C(=O)O7)C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2426512
PubChem CID:	73349261
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
Others	2

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2257	Cell Line	MCF-10A	Homo sapiens	IC50	=	27900.0	nM	PMID[564520]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	FC	=	14.2	n.a.	PMID[564520]
NPT83	Cell Line	MCF7	Homo sapiens	FC	=	7.6	n.a.	PMID[564520]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	2800.0	nM	PMID[564520]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1600.0	nM	PMID[564520]

☑ 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 NPC471382 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	306
0.1-0.2	2108
0.2-0.3	7411
0.3-0.4	16239
0.4-0.5	8813
0.5-0.6	6212
0.6-0.7	1384
0.7-0.8	185
0.8-0.85	22
0.85-0.9	11
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9541	High Similarity	NPC161060
0.945	High Similarity	NPC36754
0.9091	High Similarity	NPC471380
0.8899	High Similarity	NPC471884
0.875	High Similarity	NPC123117
0.8739	High Similarity	NPC23967
0.8704	High Similarity	NPC252234
0.8661	High Similarity	NPC209058
0.8559	High Similarity	NPC48305
0.8559	High Similarity	NPC474923
0.8532	High Similarity	NPC475217
0.8304	Intermediate Similarity	NPC475588
0.8276	Intermediate Similarity	NPC475238
0.8095	Intermediate Similarity	NPC29821
0.8095	Intermediate Similarity	NPC133888
0.8095	Intermediate Similarity	NPC57304
0.8095	Intermediate Similarity	NPC63193
0.8095	Intermediate Similarity	NPC293001
0.8095	Intermediate Similarity	NPC35959
0.8095	Intermediate Similarity	NPC171360
0.8017	Intermediate Similarity	NPC129992
0.8	Intermediate Similarity	NPC35809
0.8	Intermediate Similarity	NPC297474
0.8	Intermediate Similarity	NPC54065
0.7963	Intermediate Similarity	NPC142529
0.7963	Intermediate Similarity	NPC91771
0.7963	Intermediate Similarity	NPC18019
0.7963	Intermediate Similarity	NPC24956
0.7905	Intermediate Similarity	NPC283409
0.7905	Intermediate Similarity	NPC155935
0.789	Intermediate Similarity	NPC161493
0.787	Intermediate Similarity	NPC213698
0.7857	Intermediate Similarity	NPC474775
0.7838	Intermediate Similarity	NPC171759
0.783	Intermediate Similarity	NPC216284
0.7815	Intermediate Similarity	NPC475323
0.781	Intermediate Similarity	NPC471149
0.7805	Intermediate Similarity	NPC144625
0.7798	Intermediate Similarity	NPC213078
0.7778	Intermediate Similarity	NPC127019
0.7778	Intermediate Similarity	NPC198853
0.7757	Intermediate Similarity	NPC131209
0.7757	Intermediate Similarity	NPC133698
0.775	Intermediate Similarity	NPC475372
0.7736	Intermediate Similarity	NPC215556
0.7727	Intermediate Similarity	NPC471150
0.7714	Intermediate Similarity	NPC24728
0.7706	Intermediate Similarity	NPC476053
0.7706	Intermediate Similarity	NPC472873
0.7706	Intermediate Similarity	NPC170120
0.7706	Intermediate Similarity	NPC52044
0.7706	Intermediate Similarity	NPC67584
0.7706	Intermediate Similarity	NPC163228
0.7698	Intermediate Similarity	NPC13071
0.7686	Intermediate Similarity	NPC469380
0.7686	Intermediate Similarity	NPC312536
0.7685	Intermediate Similarity	NPC200237
0.7667	Intermediate Similarity	NPC473656
0.7642	Intermediate Similarity	NPC207114
0.7642	Intermediate Similarity	NPC217983
0.7642	Intermediate Similarity	NPC79549
0.7619	Intermediate Similarity	NPC56593
0.7615	Intermediate Similarity	NPC90453
0.7615	Intermediate Similarity	NPC262133
0.7615	Intermediate Similarity	NPC470010
0.7615	Intermediate Similarity	NPC477131
0.7615	Intermediate Similarity	NPC470013
0.7615	Intermediate Similarity	NPC323008
0.7611	Intermediate Similarity	NPC86077
0.7603	Intermediate Similarity	NPC288679
0.7593	Intermediate Similarity	NPC290651
0.7593	Intermediate Similarity	NPC286341
0.7593	Intermediate Similarity	NPC191339
0.7593	Intermediate Similarity	NPC155215
0.7589	Intermediate Similarity	NPC471381
0.7589	Intermediate Similarity	NPC186861
0.7583	Intermediate Similarity	NPC277583
0.7581	Intermediate Similarity	NPC1538
0.7581	Intermediate Similarity	NPC469352
0.7565	Intermediate Similarity	NPC243998
0.7565	Intermediate Similarity	NPC54737
0.7565	Intermediate Similarity	NPC223450
0.7563	Intermediate Similarity	NPC9848
0.7563	Intermediate Similarity	NPC312017
0.7559	Intermediate Similarity	NPC475371
0.7545	Intermediate Similarity	NPC37408
0.7544	Intermediate Similarity	NPC221421
0.7542	Intermediate Similarity	NPC474750
0.7542	Intermediate Similarity	NPC287311
0.7523	Intermediate Similarity	NPC258216
0.7523	Intermediate Similarity	NPC308656
0.7523	Intermediate Similarity	NPC473234
0.7523	Intermediate Similarity	NPC135776
0.7523	Intermediate Similarity	NPC60386
0.7523	Intermediate Similarity	NPC473263
0.7523	Intermediate Similarity	NPC473273
0.7523	Intermediate Similarity	NPC153590
0.7522	Intermediate Similarity	NPC477950
0.7521	Intermediate Similarity	NPC59489
0.7521	Intermediate Similarity	NPC139838
0.7519	Intermediate Similarity	NPC224623
0.75	Intermediate Similarity	NPC221615
0.75	Intermediate Similarity	NPC26617
0.75	Intermediate Similarity	NPC192309
0.75	Intermediate Similarity	NPC19087
0.748	Intermediate Similarity	NPC143755
0.748	Intermediate Similarity	NPC172823
0.7479	Intermediate Similarity	NPC126691
0.7478	Intermediate Similarity	NPC203659
0.7477	Intermediate Similarity	NPC126156
0.7477	Intermediate Similarity	NPC178875
0.7477	Intermediate Similarity	NPC91248
0.7458	Intermediate Similarity	NPC477103
0.7458	Intermediate Similarity	NPC475463
0.7456	Intermediate Similarity	NPC225353
0.7455	Intermediate Similarity	NPC473331
0.7453	Intermediate Similarity	NPC236692
0.7453	Intermediate Similarity	NPC187661
0.7453	Intermediate Similarity	NPC309757
0.744	Intermediate Similarity	NPC42747
0.744	Intermediate Similarity	NPC469382
0.7438	Intermediate Similarity	NPC148458
0.7431	Intermediate Similarity	NPC221282
0.7431	Intermediate Similarity	NPC184063
0.7431	Intermediate Similarity	NPC475925
0.7417	Intermediate Similarity	NPC52634
0.7414	Intermediate Similarity	NPC291643
0.7414	Intermediate Similarity	NPC190867
0.7411	Intermediate Similarity	NPC311904
0.7411	Intermediate Similarity	NPC213947
0.7411	Intermediate Similarity	NPC170143
0.7411	Intermediate Similarity	NPC169205
0.7411	Intermediate Similarity	NPC108475
0.7407	Intermediate Similarity	NPC168679
0.7407	Intermediate Similarity	NPC38392
0.7407	Intermediate Similarity	NPC12872
0.7407	Intermediate Similarity	NPC472872
0.7398	Intermediate Similarity	NPC472667
0.7391	Intermediate Similarity	NPC140723
0.7391	Intermediate Similarity	NPC110989
0.7387	Intermediate Similarity	NPC275960
0.7387	Intermediate Similarity	NPC304886
0.7387	Intermediate Similarity	NPC193645
0.7387	Intermediate Similarity	NPC90121
0.7387	Intermediate Similarity	NPC48803
0.7383	Intermediate Similarity	NPC118601
0.7381	Intermediate Similarity	NPC86346
0.7381	Intermediate Similarity	NPC75856
0.7381	Intermediate Similarity	NPC469379
0.7377	Intermediate Similarity	NPC239273
0.7377	Intermediate Similarity	NPC475305
0.7373	Intermediate Similarity	NPC477102
0.7373	Intermediate Similarity	NPC273433
0.7373	Intermediate Similarity	NPC304495
0.7368	Intermediate Similarity	NPC150923
0.7358	Intermediate Similarity	NPC284534
0.7358	Intermediate Similarity	NPC300082
0.7358	Intermediate Similarity	NPC204105
0.7355	Intermediate Similarity	NPC90472
0.7345	Intermediate Similarity	NPC141191
0.7339	Intermediate Similarity	NPC474585
0.7339	Intermediate Similarity	NPC301969
0.7339	Intermediate Similarity	NPC37607
0.7339	Intermediate Similarity	NPC4548
0.7333	Intermediate Similarity	NPC475524
0.7333	Intermediate Similarity	NPC111409
0.7333	Intermediate Similarity	NPC221144
0.7333	Intermediate Similarity	NPC100267
0.7333	Intermediate Similarity	NPC170487
0.7328	Intermediate Similarity	NPC475585
0.7328	Intermediate Similarity	NPC473577
0.7328	Intermediate Similarity	NPC474550
0.7321	Intermediate Similarity	NPC42042
0.7321	Intermediate Similarity	NPC185553
0.7317	Intermediate Similarity	NPC475401
0.7311	Intermediate Similarity	NPC179642
0.7311	Intermediate Similarity	NPC206595
0.7311	Intermediate Similarity	NPC257240
0.7304	Intermediate Similarity	NPC78127
0.7304	Intermediate Similarity	NPC471757
0.7304	Intermediate Similarity	NPC475320
0.7302	Intermediate Similarity	NPC186339
0.7295	Intermediate Similarity	NPC138372
0.7295	Intermediate Similarity	NPC106228
0.729	Intermediate Similarity	NPC304558
0.729	Intermediate Similarity	NPC67493
0.7288	Intermediate Similarity	NPC308191
0.7288	Intermediate Similarity	NPC255082
0.7287	Intermediate Similarity	NPC470851
0.7281	Intermediate Similarity	NPC218383
0.7281	Intermediate Similarity	NPC70865
0.7281	Intermediate Similarity	NPC241221
0.7281	Intermediate Similarity	NPC280963
0.7273	Intermediate Similarity	NPC184463
0.7273	Intermediate Similarity	NPC202889
0.7273	Intermediate Similarity	NPC473535
0.7273	Intermediate Similarity	NPC474937
0.7273	Intermediate Similarity	NPC208886
0.7273	Intermediate Similarity	NPC12172
0.7265	Intermediate Similarity	NPC475290

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 NPC471382 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	2786
0.2-0.3	4023
0.3-0.4	1426
0.4-0.5	352
0.5-0.6	213
0.6-0.7	20
0.7-0.8	2
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
0.7627	Intermediate Similarity	NPD6053	Discontinued
0.75	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6371	Approved
0.7248	Intermediate Similarity	NPD1695	Approved
0.686	Remote Similarity	NPD7320	Approved
0.6833	Remote Similarity	NPD6008	Approved
0.6829	Remote Similarity	NPD6650	Approved
0.6829	Remote Similarity	NPD6649	Approved
0.6803	Remote Similarity	NPD6372	Approved
0.6803	Remote Similarity	NPD6373	Approved
0.6794	Remote Similarity	NPD7507	Approved
0.6774	Remote Similarity	NPD8297	Approved
0.6759	Remote Similarity	NPD6435	Approved
0.6757	Remote Similarity	NPD4251	Approved
0.6757	Remote Similarity	NPD4250	Approved
0.6752	Remote Similarity	NPD7638	Approved
0.6742	Remote Similarity	NPD7078	Approved
0.6727	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5785	Approved
0.6721	Remote Similarity	NPD6899	Approved
0.6721	Remote Similarity	NPD6881	Approved
0.6697	Remote Similarity	NPD5362	Discontinued
0.6695	Remote Similarity	NPD7640	Approved
0.6695	Remote Similarity	NPD7639	Approved
0.6694	Remote Similarity	NPD6675	Approved
0.6694	Remote Similarity	NPD6402	Approved
0.6694	Remote Similarity	NPD7128	Approved
0.6694	Remote Similarity	NPD8130	Phase 1
0.6694	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD4249	Approved
0.6642	Remote Similarity	NPD7319	Approved
0.664	Remote Similarity	NPD6882	Approved
0.6639	Remote Similarity	NPD5697	Approved
0.6613	Remote Similarity	NPD6883	Approved
0.6613	Remote Similarity	NPD7290	Approved
0.6613	Remote Similarity	NPD7102	Approved
0.6609	Remote Similarity	NPD6399	Phase 3
0.6591	Remote Similarity	NPD7492	Approved
0.6585	Remote Similarity	NPD6686	Approved
0.6574	Remote Similarity	NPD5368	Approved
0.6567	Remote Similarity	NPD7736	Approved
0.656	Remote Similarity	NPD6617	Approved
0.656	Remote Similarity	NPD6869	Approved
0.656	Remote Similarity	NPD6847	Approved
0.6541	Remote Similarity	NPD6616	Approved
0.6538	Remote Similarity	NPD6319	Approved
0.6538	Remote Similarity	NPD6054	Approved
0.6532	Remote Similarity	NPD6012	Approved
0.6532	Remote Similarity	NPD6014	Approved
0.6532	Remote Similarity	NPD6013	Approved
0.6525	Remote Similarity	NPD6084	Phase 2
0.6525	Remote Similarity	NPD6083	Phase 2
0.6504	Remote Similarity	NPD5701	Approved
0.6493	Remote Similarity	NPD8293	Discontinued
0.6489	Remote Similarity	NPD8033	Approved
0.6457	Remote Similarity	NPD4632	Approved
0.6452	Remote Similarity	NPD6011	Approved
0.6439	Remote Similarity	NPD6370	Approved
0.6435	Remote Similarity	NPD6698	Approved
0.6435	Remote Similarity	NPD46	Approved
0.6422	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6059	Approved
0.6404	Remote Similarity	NPD6903	Approved
0.6396	Remote Similarity	NPD7154	Phase 3
0.6379	Remote Similarity	NPD7983	Approved
0.6372	Remote Similarity	NPD5786	Approved
0.6371	Remote Similarity	NPD6412	Phase 2
0.6364	Remote Similarity	NPD6015	Approved
0.6364	Remote Similarity	NPD6016	Approved
0.6364	Remote Similarity	NPD4790	Discontinued
0.6356	Remote Similarity	NPD5695	Phase 3
0.6341	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5696	Approved
0.6328	Remote Similarity	NPD8133	Approved
0.6316	Remote Similarity	NPD5988	Approved
0.6311	Remote Similarity	NPD7632	Discontinued
0.6311	Remote Similarity	NPD5211	Phase 2
0.6308	Remote Similarity	NPD6009	Approved
0.6308	Remote Similarity	NPD7115	Discovery
0.6299	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7838	Discovery
0.6288	Remote Similarity	NPD8377	Approved
0.6288	Remote Similarity	NPD8294	Approved
0.6283	Remote Similarity	NPD5363	Approved
0.6283	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5285	Approved
0.6281	Remote Similarity	NPD4696	Approved
0.6281	Remote Similarity	NPD5286	Approved
0.6273	Remote Similarity	NPD4819	Approved
0.6273	Remote Similarity	NPD4821	Approved
0.6273	Remote Similarity	NPD4822	Approved
0.6273	Remote Similarity	NPD4820	Approved
0.6271	Remote Similarity	NPD5282	Discontinued
0.6269	Remote Similarity	NPD7604	Phase 2
0.626	Remote Similarity	NPD7328	Approved
0.626	Remote Similarity	NPD7327	Approved
0.6259	Remote Similarity	NPD6845	Suspended
0.625	Remote Similarity	NPD5332	Approved
0.625	Remote Similarity	NPD5331	Approved
0.625	Remote Similarity	NPD4755	Approved
0.6241	Remote Similarity	NPD8335	Approved
0.6241	Remote Similarity	NPD8379	Approved
0.6241	Remote Similarity	NPD8378	Approved
0.6241	Remote Similarity	NPD8296	Approved
0.6241	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD8380	Approved
0.6241	Remote Similarity	NPD5983	Phase 2
0.6239	Remote Similarity	NPD8035	Phase 2
0.6239	Remote Similarity	NPD4271	Approved
0.6239	Remote Similarity	NPD8034	Phase 2
0.6239	Remote Similarity	NPD4268	Approved
0.6231	Remote Similarity	NPD6274	Approved
0.6228	Remote Similarity	NPD7521	Approved
0.6228	Remote Similarity	NPD7334	Approved
0.6228	Remote Similarity	NPD6684	Approved
0.6228	Remote Similarity	NPD6409	Approved
0.6228	Remote Similarity	NPD7146	Approved
0.6228	Remote Similarity	NPD5330	Approved
0.6218	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5369	Approved
0.6212	Remote Similarity	NPD7101	Approved
0.6212	Remote Similarity	NPD7516	Approved
0.6212	Remote Similarity	NPD7100	Approved
0.621	Remote Similarity	NPD5141	Approved
0.6198	Remote Similarity	NPD4225	Approved
0.6187	Remote Similarity	NPD7260	Phase 2
0.6186	Remote Similarity	NPD5779	Approved
0.6186	Remote Similarity	NPD5778	Approved
0.6179	Remote Similarity	NPD4633	Approved
0.6179	Remote Similarity	NPD5225	Approved
0.6179	Remote Similarity	NPD5226	Approved
0.6179	Remote Similarity	NPD5224	Approved
0.6176	Remote Similarity	NPD6336	Discontinued
0.6161	Remote Similarity	NPD4270	Approved
0.6161	Remote Similarity	NPD4269	Approved
0.6148	Remote Similarity	NPD4700	Approved
0.6136	Remote Similarity	NPD6335	Approved
0.6129	Remote Similarity	NPD5174	Approved
0.6129	Remote Similarity	NPD5175	Approved
0.6121	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD7503	Approved
0.6102	Remote Similarity	NPD6079	Approved
0.6102	Remote Similarity	NPD5284	Approved
0.6102	Remote Similarity	NPD5281	Approved
0.6102	Remote Similarity	NPD5693	Phase 1
0.6102	Remote Similarity	NPD7637	Suspended
0.6102	Remote Similarity	NPD6411	Approved
0.6098	Remote Similarity	NPD1700	Approved
0.6098	Remote Similarity	NPD5223	Approved
0.6094	Remote Similarity	NPD4634	Approved
0.6094	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD5210	Approved
0.6083	Remote Similarity	NPD4629	Approved
0.6068	Remote Similarity	NPD5328	Approved
0.6068	Remote Similarity	NPD4753	Phase 2
0.6063	Remote Similarity	NPD4730	Approved
0.6063	Remote Similarity	NPD4729	Approved
0.6061	Remote Similarity	NPD6317	Approved
0.6053	Remote Similarity	NPD4786	Approved
0.6053	Remote Similarity	NPD3133	Approved
0.6053	Remote Similarity	NPD3665	Phase 1
0.6053	Remote Similarity	NPD3666	Approved
0.6047	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD4768	Approved
0.6032	Remote Similarity	NPD4767	Approved
0.6018	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5207	Approved
0.6016	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD6313	Approved
0.6015	Remote Similarity	NPD6314	Approved
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD6908	Approved
0.6	Remote Similarity	NPD6909	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8513	Phase 3
0.6	Remote Similarity	NPD8517	Approved
0.5984	Remote Similarity	NPD7902	Approved
0.5983	Remote Similarity	NPD6672	Approved
0.5983	Remote Similarity	NPD5737	Approved
0.5982	Remote Similarity	NPD4252	Approved
0.5971	Remote Similarity	NPD6033	Approved
0.5969	Remote Similarity	NPD5250	Approved
0.5969	Remote Similarity	NPD5251	Approved
0.5969	Remote Similarity	NPD5248	Approved
0.5969	Remote Similarity	NPD5247	Approved
0.5969	Remote Similarity	NPD5249	Phase 3
0.5965	Remote Similarity	NPD4788	Approved
0.594	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5128	Approved
0.5938	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6080	Approved
0.5932	Remote Similarity	NPD6904	Approved
0.5932	Remote Similarity	NPD6673	Approved
0.5932	Remote Similarity	NPD6051	Approved
0.5932	Remote Similarity	NPD6101	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