NPASS Compound

Structure

CID324001 OpenBabel06191716172D 38 42 0 0 1 0 0 0 0 0999 V2000 0.0281 2.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0131 3.8357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2822 -2.8706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1278 -2.3822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8042 4.6871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2943 3.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4614 0.5038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8709 -1.4507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6415 -1.8943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1015 -0.4725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2814 0.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8209 -1.4209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6418 2.8392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8201 1.4207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6398 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8217 2.3667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0122 2.8539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6407 0.9473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4610 2.3653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6401 0.9463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4619 -1.4204 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1017 -1.4199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8209 1.4203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6410 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3117 2.8554 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2820 -1.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3125 3.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4616 -0.4730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8206 -0.4735 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 -5.8620 2.3623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4865 1.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9478 -1.9079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4627 4.3289 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1615 2.3638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4602 1.4188 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 8 31 1 0 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 30 1 0 0 0 0 13 31 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 32 1 0 0 0 0 17 1 1 1 0 0 0 17 25 1 0 0 0 0 18 33 2 0 0 0 0 18 37 1 0 0 0 0 19 25 2 0 0 0 0 19 32 1 0 0 0 0 20 26 1 0 0 0 0 20 34 1 6 0 0 0 21 27 1 6 0 0 0 21 38 1 0 0 0 0 22 16 1 6 0 0 0 22 25 1 0 0 0 0 22 38 1 0 0 0 0 23 28 1 0 0 0 0 23 30 1 6 0 0 0 24 28 1 0 0 0 0 24 35 2 0 0 0 0 26 30 1 1 0 0 0 26 31 1 0 0 0 0 27 29 1 0 0 0 0 27 37 1 1 0 0 0 29 36 1 0 0 0 0 30 7 1 6 0 0 0 31 32 1 6 0 0 0 32 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.36
Volume:	564.078
LogP:	4.629
LogD:	3.475
LogS:	-4.519
# Rotatable Bonds:	4
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.376
Synthetic Accessibility Score:	5.405
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
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:	-5.192
MDCK Permeability:	1.8924951291410252e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.547
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.084
30% Bioavailability (F30%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.549
Plasma Protein Binding (PPB):	86.04938507080078%
Volume Distribution (VD):	1.247
Pgp-substrate:	8.5761079788208%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.451
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.892
CYP2C9-inhibitor:	0.183
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.848
CYP3A4-substrate:	0.768

ADMET: Excretion

Clearance (CL):	6.367
Half-life (T1/2):	0.154

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.193
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.895
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.219
Carcinogencity:	0.656
Eye Corrosion:	0.006
Eye Irritation:	0.013
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: NPC324001

Natural Product ID:	NPC324001
*Common Name:**	KFWYQAKZMXFEFB-XKFNBYHKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KFWYQAKZMXFEFB-XKFNBYHKSA-N
Standard InCHI:	InChI=1S/C32H50O6/c1-17-14-21(27(29(5,6)36)37-18(2)33)38-22-16-32(9)19(25(17)22)15-20(34)26-30(7)12-11-24(35)28(3,4)23(30)10-13-31(26,32)8/h17,20-23,26-27,34,36H,10-16H2,1-9H3/t17-,20+,21+,22+,23+,26+,27-,30+,31+,32+/m1/s1
SMILES:	CC1CC(OC2C1=C3CC(C4C5(CCC(=O)C(C5CCC4(C3(C2)C)C)(C)C)C)O)C(C(C)(C)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3121590
PubChem CID:	76310823
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO3061	Alisma orientalis	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3061	Alisma orientalis	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
EC50	1
IC50	2
Others	1

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	EC50	=	25290.0	nM	PMID[488485]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Selectivity Index	=	18.5	n.a.	PMID[488484]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	5100.0	nM	PMID[488484]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	600.0	nM	PMID[488484]

☑ 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 NPC324001 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	252
0.1-0.2	1522
0.2-0.3	4457
0.3-0.4	10069
0.4-0.5	11907
0.5-0.6	6241
0.6-0.7	5496
0.7-0.8	2532
0.8-0.85	198
0.85-0.9	13
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9579	High Similarity	NPC303777
0.9579	High Similarity	NPC471784
0.93	High Similarity	NPC469318
0.93	High Similarity	NPC473173
0.9263	High Similarity	NPC30677
0.9263	High Similarity	NPC180557
0.9263	High Similarity	NPC37787
0.9263	High Similarity	NPC469329
0.9263	High Similarity	NPC473415
0.9091	High Similarity	NPC469316
0.9082	High Similarity	NPC473176
0.8969	High Similarity	NPC471777
0.8947	High Similarity	NPC473166
0.8763	High Similarity	NPC240617
0.8738	High Similarity	NPC9457
0.8738	High Similarity	NPC471783
0.8725	High Similarity	NPC473175
0.866	High Similarity	NPC198074
0.866	High Similarity	NPC274046
0.8614	High Similarity	NPC469327
0.8586	High Similarity	NPC471822
0.8526	High Similarity	NPC241875
0.8526	High Similarity	NPC469314
0.8526	High Similarity	NPC469317
0.8505	High Similarity	NPC470063
0.8462	Intermediate Similarity	NPC173172
0.8462	Intermediate Similarity	NPC475414
0.8431	Intermediate Similarity	NPC473174
0.8396	Intermediate Similarity	NPC41405
0.8396	Intermediate Similarity	NPC5475
0.8396	Intermediate Similarity	NPC173905
0.8396	Intermediate Similarity	NPC284828
0.8396	Intermediate Similarity	NPC475065
0.8396	Intermediate Similarity	NPC472216
0.8381	Intermediate Similarity	NPC144459
0.8381	Intermediate Similarity	NPC255387
0.8381	Intermediate Similarity	NPC475176
0.8381	Intermediate Similarity	NPC131665
0.8351	Intermediate Similarity	NPC469323
0.8349	Intermediate Similarity	NPC284915
0.8317	Intermediate Similarity	NPC132753
0.8317	Intermediate Similarity	NPC224356
0.8317	Intermediate Similarity	NPC151681
0.8317	Intermediate Similarity	NPC121402
0.8317	Intermediate Similarity	NPC175351
0.8302	Intermediate Similarity	NPC475418
0.8302	Intermediate Similarity	NPC318363
0.8302	Intermediate Similarity	NPC473482
0.8286	Intermediate Similarity	NPC470587
0.8283	Intermediate Similarity	NPC469315
0.8265	Intermediate Similarity	NPC472307
0.8252	Intermediate Similarity	NPC476897
0.8235	Intermediate Similarity	NPC470068
0.8218	Intermediate Similarity	NPC154526
0.8218	Intermediate Similarity	NPC472362
0.8218	Intermediate Similarity	NPC472363
0.8208	Intermediate Similarity	NPC329048
0.8208	Intermediate Similarity	NPC330011
0.8208	Intermediate Similarity	NPC301666
0.8198	Intermediate Similarity	NPC470493
0.8198	Intermediate Similarity	NPC183580
0.8198	Intermediate Similarity	NPC312824
0.8173	Intermediate Similarity	NPC32577
0.8173	Intermediate Similarity	NPC114540
0.8173	Intermediate Similarity	NPC165250
0.8173	Intermediate Similarity	NPC185530
0.8173	Intermediate Similarity	NPC155332
0.8165	Intermediate Similarity	NPC476163
0.8163	Intermediate Similarity	NPC229871
0.8163	Intermediate Similarity	NPC469319
0.8155	Intermediate Similarity	NPC473510
0.8148	Intermediate Similarity	NPC475134
0.8148	Intermediate Similarity	NPC475563
0.8144	Intermediate Similarity	NPC469322
0.8113	Intermediate Similarity	NPC472655
0.8105	Intermediate Similarity	NPC86370
0.81	Intermediate Similarity	NPC27918
0.8095	Intermediate Similarity	NPC112009
0.8095	Intermediate Similarity	NPC180204
0.8095	Intermediate Similarity	NPC26478
0.8091	Intermediate Similarity	NPC255017
0.8077	Intermediate Similarity	NPC235142
0.8077	Intermediate Similarity	NPC54909
0.8077	Intermediate Similarity	NPC233012
0.8077	Intermediate Similarity	NPC470054
0.8073	Intermediate Similarity	NPC475480
0.8073	Intermediate Similarity	NPC475668
0.8073	Intermediate Similarity	NPC473921
0.8056	Intermediate Similarity	NPC218853
0.8053	Intermediate Similarity	NPC477071
0.8053	Intermediate Similarity	NPC42673
0.8053	Intermediate Similarity	NPC264954
0.8053	Intermediate Similarity	NPC230513
0.8039	Intermediate Similarity	NPC230151
0.8037	Intermediate Similarity	NPC187435
0.8037	Intermediate Similarity	NPC473165
0.8037	Intermediate Similarity	NPC67321
0.8037	Intermediate Similarity	NPC473284
0.8036	Intermediate Similarity	NPC55296
0.8036	Intermediate Similarity	NPC286528
0.8036	Intermediate Similarity	NPC167606
0.8036	Intermediate Similarity	NPC20302
0.8036	Intermediate Similarity	NPC140055
0.8036	Intermediate Similarity	NPC470492
0.802	Intermediate Similarity	NPC91010
0.8019	Intermediate Similarity	NPC75531
0.8019	Intermediate Similarity	NPC149124
0.8018	Intermediate Similarity	NPC67259
0.8018	Intermediate Similarity	NPC472274
0.8018	Intermediate Similarity	NPC147912
0.8	Intermediate Similarity	NPC470053
0.8	Intermediate Similarity	NPC473167
0.8	Intermediate Similarity	NPC235704
0.8	Intermediate Similarity	NPC476890
0.7982	Intermediate Similarity	NPC29133
0.7982	Intermediate Similarity	NPC251226
0.7982	Intermediate Similarity	NPC5284
0.7982	Intermediate Similarity	NPC474370
0.7982	Intermediate Similarity	NPC154491
0.7982	Intermediate Similarity	NPC250956
0.7982	Intermediate Similarity	NPC268530
0.7982	Intermediate Similarity	NPC472215
0.7982	Intermediate Similarity	NPC472214
0.7981	Intermediate Similarity	NPC230546
0.7965	Intermediate Similarity	NPC473828
0.7965	Intermediate Similarity	NPC311554
0.7965	Intermediate Similarity	NPC186525
0.7965	Intermediate Similarity	NPC257457
0.7965	Intermediate Similarity	NPC50774
0.7965	Intermediate Similarity	NPC473617
0.7965	Intermediate Similarity	NPC709
0.7963	Intermediate Similarity	NPC472218
0.7963	Intermediate Similarity	NPC472217
0.7963	Intermediate Similarity	NPC472219
0.7963	Intermediate Similarity	NPC306265
0.7961	Intermediate Similarity	NPC210337
0.7946	Intermediate Similarity	NPC64318
0.7944	Intermediate Similarity	NPC60681
0.7941	Intermediate Similarity	NPC279974
0.7925	Intermediate Similarity	NPC471208
0.7925	Intermediate Similarity	NPC264048
0.7925	Intermediate Similarity	NPC476889
0.7925	Intermediate Similarity	NPC222153
0.7921	Intermediate Similarity	NPC86368
0.7921	Intermediate Similarity	NPC169343
0.7913	Intermediate Similarity	NPC4021
0.7913	Intermediate Similarity	NPC159456
0.7909	Intermediate Similarity	NPC470961
0.7905	Intermediate Similarity	NPC303559
0.7905	Intermediate Similarity	NPC93744
0.7905	Intermediate Similarity	NPC476888
0.7905	Intermediate Similarity	NPC115899
0.79	Intermediate Similarity	NPC161638
0.7895	Intermediate Similarity	NPC475041
0.789	Intermediate Similarity	NPC477070
0.789	Intermediate Similarity	NPC477069
0.7885	Intermediate Similarity	NPC119036
0.7885	Intermediate Similarity	NPC470066
0.7885	Intermediate Similarity	NPC470067
0.7885	Intermediate Similarity	NPC234617
0.7885	Intermediate Similarity	NPC124703
0.7876	Intermediate Similarity	NPC473590
0.7876	Intermediate Similarity	NPC476965
0.7876	Intermediate Similarity	NPC470959
0.7864	Intermediate Similarity	NPC475304
0.7864	Intermediate Similarity	NPC88009
0.7864	Intermediate Similarity	NPC235053
0.7864	Intermediate Similarity	NPC327179
0.7863	Intermediate Similarity	NPC469790
0.7857	Intermediate Similarity	NPC56588
0.7857	Intermediate Similarity	NPC475163
0.7857	Intermediate Similarity	NPC110861
0.7845	Intermediate Similarity	NPC88326
0.7845	Intermediate Similarity	NPC153700
0.7843	Intermediate Similarity	NPC296164
0.7843	Intermediate Similarity	NPC159410
0.7843	Intermediate Similarity	NPC471720
0.7838	Intermediate Similarity	NPC152117
0.7838	Intermediate Similarity	NPC477253
0.7838	Intermediate Similarity	NPC191620
0.7838	Intermediate Similarity	NPC234042
0.783	Intermediate Similarity	NPC40918
0.783	Intermediate Similarity	NPC476081
0.783	Intermediate Similarity	NPC473928
0.783	Intermediate Similarity	NPC295791
0.783	Intermediate Similarity	NPC283343
0.783	Intermediate Similarity	NPC473163
0.783	Intermediate Similarity	NPC258547
0.783	Intermediate Similarity	NPC273668
0.7826	Intermediate Similarity	NPC470312
0.7822	Intermediate Similarity	NPC77099
0.7822	Intermediate Similarity	NPC60755
0.7822	Intermediate Similarity	NPC285184
0.7822	Intermediate Similarity	NPC470590
0.7818	Intermediate Similarity	NPC16270
0.781	Intermediate Similarity	NPC266955
0.781	Intermediate Similarity	NPC167974
0.781	Intermediate Similarity	NPC201406
0.781	Intermediate Similarity	NPC117685
0.781	Intermediate Similarity	NPC474190

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 NPC324001 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	1812
0.2-0.3	3671
0.3-0.4	2243
0.4-0.5	726
0.5-0.6	264
0.6-0.7	173
0.7-0.8	35
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8036	Intermediate Similarity	NPD7115	Discovery
0.7727	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7638	Approved
0.767	Intermediate Similarity	NPD7748	Approved
0.7647	Intermediate Similarity	NPD7507	Approved
0.7642	Intermediate Similarity	NPD7640	Approved
0.7642	Intermediate Similarity	NPD7639	Approved
0.7568	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4225	Approved
0.7522	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD7632	Discontinued
0.7476	Intermediate Similarity	NPD7515	Phase 2
0.7476	Intermediate Similarity	NPD8035	Phase 2
0.7476	Intermediate Similarity	NPD8034	Phase 2
0.7459	Intermediate Similarity	NPD7319	Approved
0.7458	Intermediate Similarity	NPD8033	Approved
0.7456	Intermediate Similarity	NPD8133	Approved
0.7455	Intermediate Similarity	NPD6675	Approved
0.7455	Intermediate Similarity	NPD7128	Approved
0.7455	Intermediate Similarity	NPD6402	Approved
0.7455	Intermediate Similarity	NPD5739	Approved
0.7453	Intermediate Similarity	NPD7902	Approved
0.7404	Intermediate Similarity	NPD6399	Phase 3
0.74	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD8294	Approved
0.7373	Intermediate Similarity	NPD8377	Approved
0.735	Intermediate Similarity	NPD7328	Approved
0.735	Intermediate Similarity	NPD7327	Approved
0.7345	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7320	Approved
0.7321	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6899	Approved
0.7321	Intermediate Similarity	NPD6881	Approved
0.7321	Intermediate Similarity	NPD6686	Approved
0.7311	Intermediate Similarity	NPD8379	Approved
0.7311	Intermediate Similarity	NPD8296	Approved
0.7311	Intermediate Similarity	NPD8380	Approved
0.7311	Intermediate Similarity	NPD8335	Approved
0.7311	Intermediate Similarity	NPD8378	Approved
0.729	Intermediate Similarity	NPD6084	Phase 2
0.729	Intermediate Similarity	NPD6083	Phase 2
0.7288	Intermediate Similarity	NPD7516	Approved
0.7281	Intermediate Similarity	NPD8130	Phase 1
0.7265	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6372	Approved
0.7257	Intermediate Similarity	NPD6373	Approved
0.7232	Intermediate Similarity	NPD5701	Approved
0.7232	Intermediate Similarity	NPD5697	Approved
0.7232	Intermediate Similarity	NPD6412	Phase 2
0.7193	Intermediate Similarity	NPD7290	Approved
0.7193	Intermediate Similarity	NPD7102	Approved
0.7193	Intermediate Similarity	NPD6883	Approved
0.7184	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7900	Approved
0.713	Intermediate Similarity	NPD6649	Approved
0.713	Intermediate Similarity	NPD6869	Approved
0.713	Intermediate Similarity	NPD6617	Approved
0.713	Intermediate Similarity	NPD6650	Approved
0.713	Intermediate Similarity	NPD6847	Approved
0.7129	Intermediate Similarity	NPD4786	Approved
0.7105	Intermediate Similarity	NPD6013	Approved
0.7105	Intermediate Similarity	NPD6014	Approved
0.7105	Intermediate Similarity	NPD6012	Approved
0.71	Intermediate Similarity	NPD3667	Approved
0.708	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6882	Approved
0.7018	Intermediate Similarity	NPD6011	Approved
0.701	Intermediate Similarity	NPD6117	Approved
0.7009	Intermediate Similarity	NPD4632	Approved
0.699	Remote Similarity	NPD5330	Approved
0.699	Remote Similarity	NPD7146	Approved
0.699	Remote Similarity	NPD7521	Approved
0.699	Remote Similarity	NPD6409	Approved
0.699	Remote Similarity	NPD3618	Phase 1
0.699	Remote Similarity	NPD6684	Approved
0.699	Remote Similarity	NPD7334	Approved
0.6983	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4755	Approved
0.696	Remote Similarity	NPD7736	Approved
0.6952	Remote Similarity	NPD5328	Approved
0.6944	Remote Similarity	NPD5695	Phase 3
0.6942	Remote Similarity	NPD6319	Approved
0.6939	Remote Similarity	NPD6116	Phase 1
0.6937	Remote Similarity	NPD4159	Approved
0.6916	Remote Similarity	NPD4202	Approved
0.6911	Remote Similarity	NPD8328	Phase 3
0.6909	Remote Similarity	NPD5696	Approved
0.6885	Remote Similarity	NPD7503	Approved
0.6875	Remote Similarity	NPD5211	Phase 2
0.6869	Remote Similarity	NPD6115	Approved
0.6869	Remote Similarity	NPD6697	Approved
0.6869	Remote Similarity	NPD6118	Approved
0.6869	Remote Similarity	NPD6114	Approved
0.6857	Remote Similarity	NPD6903	Approved
0.6847	Remote Similarity	NPD5286	Approved
0.6847	Remote Similarity	NPD4700	Approved
0.6847	Remote Similarity	NPD4696	Approved
0.6847	Remote Similarity	NPD5285	Approved
0.6822	Remote Similarity	NPD6079	Approved
0.6822	Remote Similarity	NPD6411	Approved
0.6822	Remote Similarity	NPD5693	Phase 1
0.6804	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3665	Phase 1
0.6796	Remote Similarity	NPD3666	Approved
0.6796	Remote Similarity	NPD3133	Approved
0.6792	Remote Similarity	NPD6051	Approved
0.6792	Remote Similarity	NPD4753	Phase 2
0.6789	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD3573	Approved
0.6754	Remote Similarity	NPD5141	Approved
0.6752	Remote Similarity	NPD6371	Approved
0.675	Remote Similarity	NPD6274	Approved
0.6748	Remote Similarity	NPD8513	Phase 3
0.6748	Remote Similarity	NPD8517	Approved
0.6748	Remote Similarity	NPD8516	Approved
0.6748	Remote Similarity	NPD8515	Approved
0.6746	Remote Similarity	NPD8293	Discontinued
0.6733	Remote Similarity	NPD7525	Registered
0.6731	Remote Similarity	NPD1694	Approved
0.6729	Remote Similarity	NPD46	Approved
0.6729	Remote Similarity	NPD6698	Approved
0.6726	Remote Similarity	NPD5226	Approved
0.6726	Remote Similarity	NPD5224	Approved
0.6726	Remote Similarity	NPD4633	Approved
0.6726	Remote Similarity	NPD5225	Approved
0.6721	Remote Similarity	NPD7100	Approved
0.6721	Remote Similarity	NPD7101	Approved
0.672	Remote Similarity	NPD7492	Approved
0.6699	Remote Similarity	NPD4788	Approved
0.6698	Remote Similarity	NPD5737	Approved
0.6698	Remote Similarity	NPD6672	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6695	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.664	Remote Similarity	NPD7604	Phase 2
0.6639	Remote Similarity	NPD6053	Discontinued
0.6639	Remote Similarity	NPD6335	Approved
0.6638	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5223	Approved
0.6636	Remote Similarity	NPD6080	Approved
0.6636	Remote Similarity	NPD6904	Approved
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD6673	Approved
0.6636	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD3668	Phase 3
0.6634	Remote Similarity	NPD7645	Phase 2
0.6614	Remote Similarity	NPD7078	Approved
0.6613	Remote Similarity	NPD6921	Approved
0.6613	Remote Similarity	NPD6909	Approved
0.6613	Remote Similarity	NPD6908	Approved
0.6613	Remote Similarity	NPD5983	Phase 2
0.661	Remote Similarity	NPD4634	Approved
0.6609	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5777	Approved
0.6598	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5222	Approved
0.6577	Remote Similarity	NPD4697	Phase 3
0.6577	Remote Similarity	NPD5221	Approved
0.6574	Remote Similarity	NPD5785	Approved
0.6566	Remote Similarity	NPD3702	Approved
0.6562	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6370	Approved
0.6557	Remote Similarity	NPD6317	Approved
0.6552	Remote Similarity	NPD4767	Approved
0.6552	Remote Similarity	NPD4768	Approved
0.6538	Remote Similarity	NPD7154	Phase 3
0.6538	Remote Similarity	NPD5362	Discontinued
0.6535	Remote Similarity	NPD6336	Discontinued
0.6522	Remote Similarity	NPD4754	Approved
0.6518	Remote Similarity	NPD5173	Approved
0.6514	Remote Similarity	NPD7637	Suspended
0.6504	Remote Similarity	NPD6313	Approved
0.6504	Remote Similarity	NPD6314	Approved
0.6495	Remote Similarity	NPD4244	Approved
0.6495	Remote Similarity	NPD4245	Approved
0.6491	Remote Similarity	NPD5344	Discontinued
0.6486	Remote Similarity	NPD4629	Approved
0.6486	Remote Similarity	NPD5210	Approved
0.648	Remote Similarity	NPD6015	Approved
0.648	Remote Similarity	NPD6016	Approved
0.6475	Remote Similarity	NPD6868	Approved
0.6455	Remote Similarity	NPD5778	Approved
0.6455	Remote Similarity	NPD5779	Approved
0.6449	Remote Similarity	NPD7524	Approved
0.6442	Remote Similarity	NPD4221	Approved
0.6442	Remote Similarity	NPD4223	Phase 3
0.6441	Remote Similarity	NPD4729	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