NPASS Compound

Structure

NPC154363 OpenBabel07101719132D 34 37 0 0 1 0 0 0 0 0999 V2000 -2.5305 4.5384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8136 3.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2521 -1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5903 0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9033 2.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7169 -1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5454 3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4921 -0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4412 -3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7541 -2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0938 -4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6870 3.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3011 -1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4452 -3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -2.2764 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 -1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8884 -1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9921 -2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7019 2.0257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 -0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1073 -4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7468 0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5799 -3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5753 1.5387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3265 -1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 1.5128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 25 1 0 0 0 0 7 25 1 0 0 0 0 8 13 2 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 17 1 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 28 1 0 0 0 0 13 24 1 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 15 26 1 6 0 0 0 16 29 2 0 0 0 0 16 34 1 0 0 0 0 18 10 1 1 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 26 1 1 0 0 0 20 22 1 0 0 0 0 20 26 1 6 0 0 0 21 30 2 0 0 0 0 22 25 1 0 0 0 0 22 27 1 6 0 0 0 23 27 1 1 0 0 0 23 33 1 0 0 0 0 24 31 2 0 0 0 0 24 33 1 0 0 0 0 25 27 1 0 0 0 0 26 32 1 6 0 0 0 27 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.25
Volume:	487.035
LogP:	2.98
LogD:	1.795
LogS:	-4.158
# Rotatable Bonds:	6
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	5.257
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.823
MDCK Permeability:	2.008117917284835e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.124
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.578

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.516
Plasma Protein Binding (PPB):	52.8074951171875%
Volume Distribution (VD):	1.241
Pgp-substrate:	27.440122604370117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.366
CYP2C19-substrate:	0.614
CYP2C9-inhibitor:	0.669
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.088
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.795
CYP3A4-substrate:	0.298

ADMET: Excretion

Clearance (CL):	3.748
Half-life (T1/2):	0.841

ADMET: Toxicity

hERG Blockers:	0.792
Human Hepatotoxicity (H-HT):	0.983
Drug-inuced Liver Injury (DILI):	0.84
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.697
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.466
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC154363

Natural Product ID:	NPC154363
*Common Name:**	KFNWMXLJLRPJCL-WYEIHJKRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KFNWMXLJLRPJCL-WYEIHJKRSA-N
Standard InCHI:	InChI=1S/C27H36O7/c1-8-13(2)24(31)33-23-15(4)26(32)19-9-14(3)21(30)18(19)10-17(12-28)11-20(26)22-25(6,7)27(22,23)34-16(5)29/h8-9,11,15,18-20,22-23,28,32H,10,12H2,1-7H3/b13-8+/t15-,18-,19-,20+,22-,23-,26+,27-/m1/s1
SMILES:	C/C=C(C)/C(=O)O[C@@H]1[C@@H](C)[C@@]2([C@@H]3C=C(C)C(=O)[C@@H]3CC(=C[C@H]2[C@@H]2C(C)(C)[C@]12OC(=O)C)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375780
PubChem CID:	73347289
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

*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
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049973]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701597]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25819096]
NPO40822	Croton damayeshu	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117522]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	5
Others	2

Activity Type	# Activity
Cell Line	6
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT890	Cell Line	SNU-387	Homo sapiens	IC50	>	10000.0	nM	PMID[490197]
NPT81	Cell Line	A549	Homo sapiens	Inhibition	<	50.0	%	PMID[490198]
NPT116	Cell Line	HL-60	Homo sapiens	Inhibition	<	50.0	%	PMID[490198]
NPT1229	Cell Line	Huh-7	Homo sapiens	IC50	=	3360.0	nM	PMID[490199]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8500.0	nM	PMID[490199]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	70.0	nM	PMID[490199]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	IC50	=	20500.0	nM	PMID[490199]

☑ 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 NPC154363 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	240
0.1-0.2	1426
0.2-0.3	4178
0.3-0.4	6663
0.4-0.5	13743
0.5-0.6	8315
0.6-0.7	6273
0.7-0.8	1639
0.8-0.85	95
0.85-0.9	30
0.9-0.95	57
0.95-1	38

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471127
1.0	High Similarity	NPC234858
0.9907	High Similarity	NPC10721
0.9811	High Similarity	NPC472757
0.9725	High Similarity	NPC236918
0.9725	High Similarity	NPC156745
0.972	High Similarity	NPC472400
0.9636	High Similarity	NPC145182
0.9636	High Similarity	NPC472759
0.9636	High Similarity	NPC157252
0.9636	High Similarity	NPC329080
0.9636	High Similarity	NPC475885
0.9636	High Similarity	NPC471128
0.9636	High Similarity	NPC471126
0.9633	High Similarity	NPC124676
0.9633	High Similarity	NPC146280
0.955	High Similarity	NPC52839
0.9455	High Similarity	NPC471125
0.9455	High Similarity	NPC472758
0.9455	High Similarity	NPC171905
0.9455	High Similarity	NPC472397
0.9381	High Similarity	NPC472399
0.9369	High Similarity	NPC22628
0.9369	High Similarity	NPC471108
0.9369	High Similarity	NPC5991
0.9369	High Similarity	NPC5989
0.9369	High Similarity	NPC275696
0.9369	High Similarity	NPC255081
0.9364	High Similarity	NPC156252
0.9298	High Similarity	NPC145238
0.9292	High Similarity	NPC257017
0.9292	High Similarity	NPC162009
0.9266	High Similarity	NPC71889
0.9204	High Similarity	NPC472401
0.9182	High Similarity	NPC474872
0.9123	High Similarity	NPC19464
0.9083	High Similarity	NPC174471
0.9083	High Similarity	NPC260786
0.9083	High Similarity	NPC474871
0.9083	High Similarity	NPC475937
0.9083	High Similarity	NPC96739
0.9083	High Similarity	NPC158523
0.9	High Similarity	NPC101825
0.9	High Similarity	NPC89227
0.9	High Similarity	NPC17138
0.9	High Similarity	NPC170212
0.9	High Similarity	NPC475391
0.9	High Similarity	NPC151216
0.9	High Similarity	NPC221511
0.9	High Similarity	NPC265499
0.9	High Similarity	NPC215643
0.8991	High Similarity	NPC153036
0.8947	High Similarity	NPC19336
0.8947	High Similarity	NPC185876
0.8938	High Similarity	NPC472760
0.8919	High Similarity	NPC474937
0.8898	High Similarity	NPC270109
0.886	High Similarity	NPC180640
0.876	High Similarity	NPC476111
0.8729	High Similarity	NPC222307
0.8727	High Similarity	NPC273433
0.8727	High Similarity	NPC163004
0.8696	High Similarity	NPC472667
0.8684	High Similarity	NPC153651
0.8644	High Similarity	NPC473919
0.8644	High Similarity	NPC473709
0.8584	High Similarity	NPC477091
0.8559	High Similarity	NPC473802
0.8545	High Similarity	NPC67321
0.8545	High Similarity	NPC187435
0.8525	High Similarity	NPC90814
0.8525	High Similarity	NPC189393
0.85	High Similarity	NPC471940
0.8462	Intermediate Similarity	NPC143755
0.843	Intermediate Similarity	NPC236999
0.8417	Intermediate Similarity	NPC293112
0.8417	Intermediate Similarity	NPC471939
0.8407	Intermediate Similarity	NPC469655
0.8407	Intermediate Similarity	NPC469656
0.8407	Intermediate Similarity	NPC474846
0.839	Intermediate Similarity	NPC310511
0.8378	Intermediate Similarity	NPC143609
0.8362	Intermediate Similarity	NPC469684
0.8349	Intermediate Similarity	NPC476081
0.8333	Intermediate Similarity	NPC472002
0.8319	Intermediate Similarity	NPC253906
0.8319	Intermediate Similarity	NPC257240
0.8304	Intermediate Similarity	NPC306265
0.8288	Intermediate Similarity	NPC111952
0.8279	Intermediate Similarity	NPC470850
0.8276	Intermediate Similarity	NPC470793
0.8276	Intermediate Similarity	NPC471816
0.8276	Intermediate Similarity	NPC179626
0.8254	Intermediate Similarity	NPC243902
0.825	Intermediate Similarity	NPC11895
0.825	Intermediate Similarity	NPC469789
0.8235	Intermediate Similarity	NPC67569
0.822	Intermediate Similarity	NPC475041
0.822	Intermediate Similarity	NPC469380
0.8211	Intermediate Similarity	NPC104382
0.8211	Intermediate Similarity	NPC470851
0.8205	Intermediate Similarity	NPC475323
0.8205	Intermediate Similarity	NPC473656
0.8182	Intermediate Similarity	NPC172154
0.8182	Intermediate Similarity	NPC162973
0.8182	Intermediate Similarity	NPC81736
0.8182	Intermediate Similarity	NPC137430
0.8174	Intermediate Similarity	NPC470063
0.8174	Intermediate Similarity	NPC269530
0.8167	Intermediate Similarity	NPC23786
0.8167	Intermediate Similarity	NPC470265
0.8167	Intermediate Similarity	NPC170538
0.8165	Intermediate Similarity	NPC470074
0.8165	Intermediate Similarity	NPC47024
0.8165	Intermediate Similarity	NPC474718
0.8158	Intermediate Similarity	NPC5103
0.8158	Intermediate Similarity	NPC477103
0.8151	Intermediate Similarity	NPC268530
0.8151	Intermediate Similarity	NPC4548
0.8151	Intermediate Similarity	NPC154491
0.8142	Intermediate Similarity	NPC469916
0.8142	Intermediate Similarity	NPC472439
0.812	Intermediate Similarity	NPC176840
0.8115	Intermediate Similarity	NPC473635
0.8108	Intermediate Similarity	NPC99266
0.8108	Intermediate Similarity	NPC120321
0.8108	Intermediate Similarity	NPC8196
0.8108	Intermediate Similarity	NPC61442
0.8103	Intermediate Similarity	NPC469463
0.8103	Intermediate Similarity	NPC469454
0.8103	Intermediate Similarity	NPC477126
0.8103	Intermediate Similarity	NPC469496
0.8103	Intermediate Similarity	NPC106395
0.8103	Intermediate Similarity	NPC471204
0.8103	Intermediate Similarity	NPC25909
0.8103	Intermediate Similarity	NPC46269
0.8099	Intermediate Similarity	NPC469352
0.8099	Intermediate Similarity	NPC473979
0.8091	Intermediate Similarity	NPC471412
0.8087	Intermediate Similarity	NPC470076
0.8087	Intermediate Similarity	NPC317107
0.8083	Intermediate Similarity	NPC159456
0.8083	Intermediate Similarity	NPC4021
0.808	Intermediate Similarity	NPC475139
0.808	Intermediate Similarity	NPC180902
0.8073	Intermediate Similarity	NPC216478
0.807	Intermediate Similarity	NPC475586
0.807	Intermediate Similarity	NPC469370
0.807	Intermediate Similarity	NPC477102
0.8067	Intermediate Similarity	NPC312536
0.8067	Intermediate Similarity	NPC470186
0.8065	Intermediate Similarity	NPC175186
0.8065	Intermediate Similarity	NPC231529
0.8056	Intermediate Similarity	NPC202833
0.8056	Intermediate Similarity	NPC472995
0.8056	Intermediate Similarity	NPC284518
0.8053	Intermediate Similarity	NPC180744
0.8051	Intermediate Similarity	NPC58662
0.8051	Intermediate Similarity	NPC284068
0.8051	Intermediate Similarity	NPC473968
0.8051	Intermediate Similarity	NPC183580
0.8051	Intermediate Similarity	NPC53396
0.8051	Intermediate Similarity	NPC98249
0.8051	Intermediate Similarity	NPC470493
0.8051	Intermediate Similarity	NPC312824
0.8051	Intermediate Similarity	NPC13713
0.8036	Intermediate Similarity	NPC118911
0.8036	Intermediate Similarity	NPC146731
0.8036	Intermediate Similarity	NPC296950
0.8034	Intermediate Similarity	NPC133677
0.8034	Intermediate Similarity	NPC238667
0.8034	Intermediate Similarity	NPC138303
0.8034	Intermediate Similarity	NPC67290
0.8033	Intermediate Similarity	NPC8369
0.8018	Intermediate Similarity	NPC472552
0.8018	Intermediate Similarity	NPC475038
0.8018	Intermediate Similarity	NPC109195
0.8018	Intermediate Similarity	NPC474709
0.8018	Intermediate Similarity	NPC295791
0.8017	Intermediate Similarity	NPC234042
0.8017	Intermediate Similarity	NPC269642
0.8017	Intermediate Similarity	NPC236217
0.8017	Intermediate Similarity	NPC76550
0.8017	Intermediate Similarity	NPC138757
0.8017	Intermediate Similarity	NPC152117
0.8017	Intermediate Similarity	NPC317687
0.8017	Intermediate Similarity	NPC123855
0.8017	Intermediate Similarity	NPC222688
0.8	Intermediate Similarity	NPC48692
0.8	Intermediate Similarity	NPC471170
0.8	Intermediate Similarity	NPC471413
0.8	Intermediate Similarity	NPC472214
0.8	Intermediate Similarity	NPC475003
0.8	Intermediate Similarity	NPC38855
0.8	Intermediate Similarity	NPC251226
0.8	Intermediate Similarity	NPC472215
0.7983	Intermediate Similarity	NPC709
0.7983	Intermediate Similarity	NPC186525
0.7983	Intermediate Similarity	NPC159928
0.7983	Intermediate Similarity	NPC50774

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 NPC154363 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1832
0.2-0.3	3592
0.3-0.4	2226
0.4-0.5	857
0.5-0.6	271
0.6-0.7	152
0.7-0.8	11
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8319	Intermediate Similarity	NPD6371	Approved
0.7928	Intermediate Similarity	NPD5344	Discontinued
0.7913	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD7115	Discovery
0.7845	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6648	Approved
0.7589	Intermediate Similarity	NPD4225	Approved
0.7586	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD7640	Approved
0.7522	Intermediate Similarity	NPD7639	Approved
0.7521	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7638	Approved
0.7373	Intermediate Similarity	NPD6686	Approved
0.7273	Intermediate Similarity	NPD46	Approved
0.7273	Intermediate Similarity	NPD6698	Approved
0.7273	Intermediate Similarity	NPD8297	Approved
0.7266	Intermediate Similarity	NPD7507	Approved
0.7244	Intermediate Similarity	NPD7604	Phase 2
0.7231	Intermediate Similarity	NPD7319	Approved
0.7227	Intermediate Similarity	NPD6899	Approved
0.7227	Intermediate Similarity	NPD6881	Approved
0.7213	Intermediate Similarity	NPD4632	Approved
0.7203	Intermediate Similarity	NPD7128	Approved
0.7203	Intermediate Similarity	NPD5739	Approved
0.7203	Intermediate Similarity	NPD6675	Approved
0.7203	Intermediate Similarity	NPD6008	Approved
0.7203	Intermediate Similarity	NPD6402	Approved
0.72	Intermediate Similarity	NPD7516	Approved
0.719	Intermediate Similarity	NPD6650	Approved
0.719	Intermediate Similarity	NPD6649	Approved
0.7168	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6373	Approved
0.7167	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD5697	Approved
0.7131	Intermediate Similarity	NPD6053	Discontinued
0.712	Intermediate Similarity	NPD7328	Approved
0.712	Intermediate Similarity	NPD7327	Approved
0.7107	Intermediate Similarity	NPD6883	Approved
0.7107	Intermediate Similarity	NPD7290	Approved
0.7107	Intermediate Similarity	NPD7102	Approved
0.7083	Intermediate Similarity	NPD7320	Approved
0.7054	Intermediate Similarity	NPD7492	Approved
0.7049	Intermediate Similarity	NPD6869	Approved
0.7049	Intermediate Similarity	NPD6847	Approved
0.7049	Intermediate Similarity	NPD8130	Phase 1
0.7049	Intermediate Similarity	NPD6617	Approved
0.704	Intermediate Similarity	NPD6009	Approved
0.7025	Intermediate Similarity	NPD6013	Approved
0.7025	Intermediate Similarity	NPD6012	Approved
0.7025	Intermediate Similarity	NPD6014	Approved
0.7008	Intermediate Similarity	NPD6054	Approved
0.7	Intermediate Similarity	NPD6616	Approved
0.7	Intermediate Similarity	NPD5701	Approved
0.6992	Remote Similarity	NPD6882	Approved
0.6991	Remote Similarity	NPD6399	Phase 3
0.6953	Remote Similarity	NPD5983	Phase 2
0.6949	Remote Similarity	NPD5211	Phase 2
0.6949	Remote Similarity	NPD7632	Discontinued
0.6947	Remote Similarity	NPD7078	Approved
0.6942	Remote Similarity	NPD6011	Approved
0.6899	Remote Similarity	NPD6370	Approved
0.6897	Remote Similarity	NPD7902	Approved
0.6894	Remote Similarity	NPD7736	Approved
0.6875	Remote Similarity	NPD6059	Approved
0.6875	Remote Similarity	NPD1695	Approved
0.687	Remote Similarity	NPD6336	Discontinued
0.6833	Remote Similarity	NPD5141	Approved
0.6822	Remote Similarity	NPD8335	Approved
0.6822	Remote Similarity	NPD8033	Approved
0.6822	Remote Similarity	NPD8380	Approved
0.6822	Remote Similarity	NPD8378	Approved
0.6822	Remote Similarity	NPD8379	Approved
0.6822	Remote Similarity	NPD6016	Approved
0.6822	Remote Similarity	NPD8296	Approved
0.6822	Remote Similarity	NPD6015	Approved
0.6822	Remote Similarity	NPD6921	Approved
0.6818	Remote Similarity	NPD8293	Discontinued
0.6818	Remote Similarity	NPD1694	Approved
0.6814	Remote Similarity	NPD7838	Discovery
0.6814	Remote Similarity	NPD5785	Approved
0.6783	Remote Similarity	NPD7748	Approved
0.678	Remote Similarity	NPD5285	Approved
0.678	Remote Similarity	NPD5286	Approved
0.678	Remote Similarity	NPD4696	Approved
0.6774	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5988	Approved
0.6754	Remote Similarity	NPD7515	Phase 2
0.6754	Remote Similarity	NPD6079	Approved
0.6752	Remote Similarity	NPD6084	Phase 2
0.6752	Remote Similarity	NPD4755	Approved
0.6752	Remote Similarity	NPD6083	Phase 2
0.6748	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD8377	Approved
0.6744	Remote Similarity	NPD8294	Approved
0.6726	Remote Similarity	NPD5328	Approved
0.6724	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6412	Phase 2
0.6718	Remote Similarity	NPD8328	Phase 3
0.6697	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5779	Approved
0.6696	Remote Similarity	NPD5778	Approved
0.6695	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD4634	Approved
0.6693	Remote Similarity	NPD6274	Approved
0.6692	Remote Similarity	NPD8515	Approved
0.6692	Remote Similarity	NPD8513	Phase 3
0.6692	Remote Similarity	NPD7503	Approved
0.6692	Remote Similarity	NPD8517	Approved
0.6692	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD1696	Phase 3
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4700	Approved
0.6638	Remote Similarity	NPD7900	Approved
0.6638	Remote Similarity	NPD5282	Discontinued
0.6638	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7260	Phase 2
0.6612	Remote Similarity	NPD5174	Approved
0.6612	Remote Similarity	NPD5175	Approved
0.6609	Remote Similarity	NPD7637	Suspended
0.6609	Remote Similarity	NPD7983	Approved
0.6607	Remote Similarity	NPD3618	Phase 1
0.6589	Remote Similarity	NPD6335	Approved
0.6583	Remote Similarity	NPD5223	Approved
0.6581	Remote Similarity	NPD5695	Phase 3
0.6555	Remote Similarity	NPD5696	Approved
0.6552	Remote Similarity	NPD4202	Approved
0.6549	Remote Similarity	NPD7524	Approved
0.6525	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4697	Phase 3
0.6525	Remote Similarity	NPD5221	Approved
0.6525	Remote Similarity	NPD5222	Approved
0.6512	Remote Similarity	NPD6317	Approved
0.6508	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5173	Approved
0.6466	Remote Similarity	NPD8034	Phase 2
0.6466	Remote Similarity	NPD8035	Phase 2
0.6462	Remote Similarity	NPD6313	Approved
0.6462	Remote Similarity	NPD6314	Approved
0.6444	Remote Similarity	NPD8074	Phase 3
0.6439	Remote Similarity	NPD6909	Approved
0.6439	Remote Similarity	NPD6908	Approved
0.6439	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6868	Approved
0.6429	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4786	Approved
0.6404	Remote Similarity	NPD3573	Approved
0.64	Remote Similarity	NPD4729	Approved
0.64	Remote Similarity	NPD4730	Approved
0.64	Remote Similarity	NPD5128	Approved
0.6397	Remote Similarity	NPD6033	Approved
0.6385	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5363	Approved
0.6371	Remote Similarity	NPD4768	Approved
0.6371	Remote Similarity	NPD4767	Approved
0.6356	Remote Similarity	NPD6001	Approved
0.6348	Remote Similarity	NPD5737	Approved
0.6348	Remote Similarity	NPD6672	Approved
0.6341	Remote Similarity	NPD4754	Approved
0.6339	Remote Similarity	NPD5362	Discontinued
0.6339	Remote Similarity	NPD7154	Phase 3
0.6339	Remote Similarity	NPD6695	Phase 3
0.6331	Remote Similarity	NPD6845	Suspended
0.633	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5284	Approved
0.6325	Remote Similarity	NPD5693	Phase 1
0.6325	Remote Similarity	NPD5281	Approved
0.6325	Remote Similarity	NPD6411	Approved
0.6316	Remote Similarity	NPD7334	Approved
0.6316	Remote Similarity	NPD7146	Approved
0.6316	Remote Similarity	NPD5330	Approved
0.6316	Remote Similarity	NPD6684	Approved
0.6316	Remote Similarity	NPD6409	Approved
0.6316	Remote Similarity	NPD7521	Approved
0.6311	Remote Similarity	NPD1700	Approved
0.6303	Remote Similarity	NPD4629	Approved
0.6303	Remote Similarity	NPD5210	Approved
0.6299	Remote Similarity	NPD5251	Approved
0.6299	Remote Similarity	NPD5248	Approved
0.6299	Remote Similarity	NPD5249	Phase 3
0.6299	Remote Similarity	NPD5247	Approved
0.6299	Remote Similarity	NPD5250	Approved
0.6293	Remote Similarity	NPD4753	Phase 2
0.625	Remote Similarity	NPD5216	Approved
0.625	Remote Similarity	NPD3667	Approved
0.625	Remote Similarity	NPD5217	Approved
0.625	Remote Similarity	NPD5209	Approved
0.625	Remote Similarity	NPD5215	Approved
0.6239	Remote Similarity	NPD3168	Discontinued
0.6228	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6067	Discontinued
0.6207	Remote Similarity	NPD7513	Clinical (unspecified phase)

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