NPASS Compound

Structure

NPC472397 OpenBabel07101718202D 34 37 0 0 1 0 0 0 0 0999 V2000 -0.0449 -2.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7767 -2.9738 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 2.5753 -1.5387 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 3.4921 0.7376 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 2.4412 3.1110 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 -0.9033 -2.4868 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 1.7019 -2.0257 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 0.8884 1.4869 0.0000 C 0 0 1 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 0.0150 0.9999 0.0000 C 0 0 2 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 0.8584 -0.5129 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 -0.8584 0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 2.2764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7468 0.9740 0.0000 C 0 0 1 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 1.6870 -3.0256 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 -1.7468 -0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2232 2.9158 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 23 1 0 0 0 0 7 23 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 10 24 1 0 0 0 0 11 16 1 0 0 0 0 11 27 1 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 14 25 1 6 0 0 0 15 28 2 0 0 0 0 15 33 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 6 0 0 0 18 24 1 1 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 26 1 6 0 0 0 20 24 1 0 0 0 0 20 29 2 0 0 0 0 21 26 1 1 0 0 0 21 33 1 0 0 0 0 22 30 2 0 0 0 0 22 34 1 0 0 0 0 23 26 1 0 0 0 0 24 31 1 1 0 0 0 25 32 1 6 0 0 0 26 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.24
Volume:	481.166
LogP:	2.781
LogD:	1.63
LogS:	-3.971
# Rotatable Bonds:	6
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.413
Synthetic Accessibility Score:	5.109
Fsp3:	0.731
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:	-5.071
MDCK Permeability:	6.909317016834393e-05
Pgp-inhibitor:	0.965
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.154
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.174

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.385
Plasma Protein Binding (PPB):	42.51016616821289%
Volume Distribution (VD):	1.192
Pgp-substrate:	59.47228240966797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.423
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.22
CYP3A4-substrate:	0.3

ADMET: Excretion

Clearance (CL):	2.186
Half-life (T1/2):	0.439

ADMET: Toxicity

hERG Blockers:	0.579
Human Hepatotoxicity (H-HT):	0.958
Drug-inuced Liver Injury (DILI):	0.398
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.904
Maximum Recommended Daily Dose:	0.426
Skin Sensitization:	0.445
Carcinogencity:	0.144
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC472397

Natural Product ID:	NPC472397
*Common Name:**	KJIOAJURTOBZDU-OXQILEDISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KJIOAJURTOBZDU-OXQILEDISA-N
Standard InCHI:	InChI=1S/C26H36O8/c1-12(2)22(30)34-26-19(23(26,6)7)17-9-16(11-27)10-24(31)18(8-13(3)20(24)29)25(17,32)14(4)21(26)33-15(5)28/h8-9,12,14,17-19,21,27,31-32H,10-11H2,1-7H3/t14-,17+,18-,19-,21-,24-,25-,26-/m1/s1
SMILES:	OCC1=C[C@H]2[C@@H]3C([C@]3(OC(=O)C(C)C)[C@@H]([C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C)OC(=O)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3400658
PubChem CID:	n.a.
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 [CHEMONTID:0002906] Phorbol esters

*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]
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	14

Activity Type	# Activity
Cell Line	8
Individual Protein	2
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	4000.0	nM	PMID[505665]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	2400.0	nM	PMID[505665]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	13000.0	nM	PMID[505665]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3900.0	nM	PMID[505665]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	7200.0	nM	PMID[505665]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5800.0	nM	PMID[505665]
NPT2341	Cell Line	NCI-H1975	Homo sapiens	IC50	=	10000.0	nM	PMID[505665]
NPT2615	Cell Line	HEK-293T	Homo sapiens	IC50	=	291600.0	nM	PMID[505665]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	50000.0	nM	PMID[505665]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	50000.0	nM	PMID[505665]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6800.0	nM	PMID[505665]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13000.0	nM	PMID[505665]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12000.0	nM	PMID[505665]
NPT27	Others	Unspecified		IC50	>	500000.0	nM	PMID[505665]

☑ 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 NPC472397 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	241
0.1-0.2	1453
0.2-0.3	4441
0.3-0.4	7380
0.4-0.5	13693
0.5-0.6	8023
0.6-0.7	5958
0.7-0.8	1340
0.8-0.85	45
0.85-0.9	35
0.9-0.95	51
0.95-1	37

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471125
1.0	High Similarity	NPC171905
1.0	High Similarity	NPC472758
0.9908	High Similarity	NPC22628
0.9908	High Similarity	NPC275696
0.9908	High Similarity	NPC255081
0.9908	High Similarity	NPC5989
0.9908	High Similarity	NPC471108
0.9908	High Similarity	NPC5991
0.9818	High Similarity	NPC471128
0.9818	High Similarity	NPC157252
0.9818	High Similarity	NPC471126
0.9818	High Similarity	NPC145182
0.973	High Similarity	NPC472401
0.973	High Similarity	NPC52839
0.9725	High Similarity	NPC156252
0.9643	High Similarity	NPC19464
0.963	High Similarity	NPC472757
0.9558	High Similarity	NPC472399
0.9541	High Similarity	NPC472400
0.9474	High Similarity	NPC145238
0.9469	High Similarity	NPC162009
0.9469	High Similarity	NPC257017
0.9455	High Similarity	NPC471127
0.9455	High Similarity	NPC234858
0.9455	High Similarity	NPC154363
0.9444	High Similarity	NPC158523
0.9444	High Similarity	NPC475937
0.9369	High Similarity	NPC10721
0.9364	High Similarity	NPC474872
0.9352	High Similarity	NPC153036
0.9273	High Similarity	NPC71889
0.9204	High Similarity	NPC156745
0.9204	High Similarity	NPC236918
0.9196	High Similarity	NPC153651
0.9182	High Similarity	NPC475391
0.9123	High Similarity	NPC472759
0.9123	High Similarity	NPC329080
0.9123	High Similarity	NPC185876
0.9123	High Similarity	NPC475885
0.9123	High Similarity	NPC19336
0.9115	High Similarity	NPC124676
0.9115	High Similarity	NPC146280
0.9099	High Similarity	NPC474937
0.9091	High Similarity	NPC96739
0.9091	High Similarity	NPC174471
0.9091	High Similarity	NPC260786
0.9091	High Similarity	NPC474871
0.9083	High Similarity	NPC163004
0.9068	High Similarity	NPC270109
0.9035	High Similarity	NPC180640
0.9009	High Similarity	NPC17138
0.9009	High Similarity	NPC215643
0.9009	High Similarity	NPC89227
0.9009	High Similarity	NPC170212
0.9009	High Similarity	NPC265499
0.9009	High Similarity	NPC101825
0.9009	High Similarity	NPC151216
0.9009	High Similarity	NPC221511
0.8947	High Similarity	NPC472760
0.8929	High Similarity	NPC477091
0.8898	High Similarity	NPC222307
0.8814	High Similarity	NPC473919
0.8814	High Similarity	NPC473709
0.8729	High Similarity	NPC473802
0.871	High Similarity	NPC243902
0.8667	High Similarity	NPC471940
0.8595	High Similarity	NPC236999
0.8583	High Similarity	NPC471939
0.8547	High Similarity	NPC472667
0.8487	Intermediate Similarity	NPC222688
0.8448	Intermediate Similarity	NPC179626
0.8407	Intermediate Similarity	NPC273433
0.8387	Intermediate Similarity	NPC90814
0.8387	Intermediate Similarity	NPC189393
0.832	Intermediate Similarity	NPC476111
0.8319	Intermediate Similarity	NPC143755
0.8305	Intermediate Similarity	NPC251310
0.825	Intermediate Similarity	NPC310511
0.824	Intermediate Similarity	NPC180902
0.824	Intermediate Similarity	NPC475139
0.8205	Intermediate Similarity	NPC473798
0.819	Intermediate Similarity	NPC472002
0.819	Intermediate Similarity	NPC474516
0.8145	Intermediate Similarity	NPC470850
0.8136	Intermediate Similarity	NPC40632
0.8136	Intermediate Similarity	NPC328374
0.8136	Intermediate Similarity	NPC251236
0.8136	Intermediate Similarity	NPC470793
0.8136	Intermediate Similarity	NPC96312
0.8136	Intermediate Similarity	NPC474734
0.813	Intermediate Similarity	NPC217901
0.812	Intermediate Similarity	NPC250109
0.812	Intermediate Similarity	NPC73300
0.812	Intermediate Similarity	NPC477126
0.812	Intermediate Similarity	NPC962
0.812	Intermediate Similarity	NPC108721
0.812	Intermediate Similarity	NPC49451
0.811	Intermediate Similarity	NPC182266
0.811	Intermediate Similarity	NPC475154
0.811	Intermediate Similarity	NPC476823
0.811	Intermediate Similarity	NPC100017
0.811	Intermediate Similarity	NPC475500
0.811	Intermediate Similarity	NPC471136
0.811	Intermediate Similarity	NPC471137
0.811	Intermediate Similarity	NPC223356
0.811	Intermediate Similarity	NPC473548
0.808	Intermediate Similarity	NPC470851
0.808	Intermediate Similarity	NPC162495
0.808	Intermediate Similarity	NPC104382
0.807	Intermediate Similarity	NPC143609
0.807	Intermediate Similarity	NPC67321
0.807	Intermediate Similarity	NPC187435
0.8067	Intermediate Similarity	NPC474654
0.8067	Intermediate Similarity	NPC470854
0.8067	Intermediate Similarity	NPC97908
0.8067	Intermediate Similarity	NPC287343
0.8067	Intermediate Similarity	NPC176513
0.8067	Intermediate Similarity	NPC122033
0.8067	Intermediate Similarity	NPC471854
0.8067	Intermediate Similarity	NPC470775
0.8065	Intermediate Similarity	NPC470882
0.8065	Intermediate Similarity	NPC168849
0.8065	Intermediate Similarity	NPC475273
0.8034	Intermediate Similarity	NPC317687
0.8031	Intermediate Similarity	NPC469673
0.8018	Intermediate Similarity	NPC470074
0.8017	Intermediate Similarity	NPC5103
0.8017	Intermediate Similarity	NPC257240
0.8017	Intermediate Similarity	NPC112038
0.8017	Intermediate Similarity	NPC4548
0.8017	Intermediate Similarity	NPC109973
0.8017	Intermediate Similarity	NPC472004
0.8017	Intermediate Similarity	NPC477103
0.8016	Intermediate Similarity	NPC220757
0.8016	Intermediate Similarity	NPC475314
0.8016	Intermediate Similarity	NPC196921
0.8016	Intermediate Similarity	NPC475606
0.8016	Intermediate Similarity	NPC477189
0.8016	Intermediate Similarity	NPC251564
0.8	Intermediate Similarity	NPC476479
0.8	Intermediate Similarity	NPC29827
0.7984	Intermediate Similarity	NPC293112
0.7984	Intermediate Similarity	NPC15095
0.7984	Intermediate Similarity	NPC68282
0.7984	Intermediate Similarity	NPC225049
0.7983	Intermediate Similarity	NPC266728
0.7983	Intermediate Similarity	NPC270958
0.7983	Intermediate Similarity	NPC49492
0.7982	Intermediate Similarity	NPC60315
0.7982	Intermediate Similarity	NPC111952
0.7967	Intermediate Similarity	NPC67251
0.7966	Intermediate Similarity	NPC469463
0.7966	Intermediate Similarity	NPC202889
0.7966	Intermediate Similarity	NPC474271
0.7966	Intermediate Similarity	NPC208998
0.7966	Intermediate Similarity	NPC317210
0.7966	Intermediate Similarity	NPC469454
0.7966	Intermediate Similarity	NPC469496
0.7966	Intermediate Similarity	NPC7921
0.7965	Intermediate Similarity	NPC475623
0.7965	Intermediate Similarity	NPC475334
0.7965	Intermediate Similarity	NPC473694
0.7953	Intermediate Similarity	NPC473485
0.7953	Intermediate Similarity	NPC34963
0.7953	Intermediate Similarity	NPC474508
0.7951	Intermediate Similarity	NPC477046
0.7951	Intermediate Similarity	NPC102822
0.7949	Intermediate Similarity	NPC475668
0.7949	Intermediate Similarity	NPC473921
0.7949	Intermediate Similarity	NPC469655
0.7949	Intermediate Similarity	NPC469656
0.7949	Intermediate Similarity	NPC317107
0.7949	Intermediate Similarity	NPC474846
0.7949	Intermediate Similarity	NPC475480
0.7937	Intermediate Similarity	NPC175186
0.7937	Intermediate Similarity	NPC35109
0.7937	Intermediate Similarity	NPC231529
0.7937	Intermediate Similarity	NPC470880
0.7934	Intermediate Similarity	NPC476529
0.7934	Intermediate Similarity	NPC472933
0.7934	Intermediate Similarity	NPC475041
0.7934	Intermediate Similarity	NPC475775
0.7934	Intermediate Similarity	NPC469380
0.7931	Intermediate Similarity	NPC471934
0.7931	Intermediate Similarity	NPC477102
0.7931	Intermediate Similarity	NPC141350
0.7931	Intermediate Similarity	NPC42662
0.792	Intermediate Similarity	NPC473253
0.792	Intermediate Similarity	NPC473265
0.7917	Intermediate Similarity	NPC469684
0.7917	Intermediate Similarity	NPC473590
0.7917	Intermediate Similarity	NPC296822
0.7913	Intermediate Similarity	NPC474716
0.7913	Intermediate Similarity	NPC3316
0.7913	Intermediate Similarity	NPC144854
0.7903	Intermediate Similarity	NPC81736
0.7903	Intermediate Similarity	NPC172154
0.7903	Intermediate Similarity	NPC476729
0.7903	Intermediate Similarity	NPC24651

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 NPC472397 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1922
0.2-0.3	3667
0.3-0.4	2150
0.4-0.5	782
0.5-0.6	244
0.6-0.7	159
0.7-0.8	16
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
0.8017	Intermediate Similarity	NPD6371	Approved
0.7731	Intermediate Similarity	NPD8297	Approved
0.7647	Intermediate Similarity	NPD6650	Approved
0.7647	Intermediate Similarity	NPD6649	Approved
0.7627	Intermediate Similarity	NPD6372	Approved
0.7627	Intermediate Similarity	NPD6373	Approved
0.7581	Intermediate Similarity	NPD6319	Approved
0.7563	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6899	Approved
0.7542	Intermediate Similarity	NPD6881	Approved
0.754	Intermediate Similarity	NPD7604	Phase 2
0.7521	Intermediate Similarity	NPD7128	Approved
0.7521	Intermediate Similarity	NPD6402	Approved
0.7521	Intermediate Similarity	NPD5739	Approved
0.7521	Intermediate Similarity	NPD4632	Approved
0.7521	Intermediate Similarity	NPD6675	Approved
0.748	Intermediate Similarity	NPD7115	Discovery
0.7479	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD5344	Discontinued
0.7458	Intermediate Similarity	NPD5697	Approved
0.7438	Intermediate Similarity	NPD6882	Approved
0.7417	Intermediate Similarity	NPD7102	Approved
0.7417	Intermediate Similarity	NPD6883	Approved
0.7417	Intermediate Similarity	NPD7290	Approved
0.7395	Intermediate Similarity	NPD7320	Approved
0.7395	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD8130	Phase 1
0.7355	Intermediate Similarity	NPD6617	Approved
0.7355	Intermediate Similarity	NPD6869	Approved
0.7355	Intermediate Similarity	NPD6847	Approved
0.7344	Intermediate Similarity	NPD7492	Approved
0.7339	Intermediate Similarity	NPD6009	Approved
0.7333	Intermediate Similarity	NPD6013	Approved
0.7333	Intermediate Similarity	NPD6014	Approved
0.7333	Intermediate Similarity	NPD6012	Approved
0.7311	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5701	Approved
0.7302	Intermediate Similarity	NPD6054	Approved
0.7287	Intermediate Similarity	NPD6616	Approved
0.7265	Intermediate Similarity	NPD5211	Phase 2
0.725	Intermediate Similarity	NPD6011	Approved
0.7244	Intermediate Similarity	NPD5983	Phase 2
0.7241	Intermediate Similarity	NPD7640	Approved
0.7241	Intermediate Similarity	NPD7639	Approved
0.7241	Intermediate Similarity	NPD6648	Approved
0.7231	Intermediate Similarity	NPD7078	Approved
0.7227	Intermediate Similarity	NPD6008	Approved
0.7188	Intermediate Similarity	NPD6370	Approved
0.7176	Intermediate Similarity	NPD7736	Approved
0.7165	Intermediate Similarity	NPD6059	Approved
0.7155	Intermediate Similarity	NPD4225	Approved
0.7155	Intermediate Similarity	NPD7638	Approved
0.7154	Intermediate Similarity	NPD7507	Approved
0.7154	Intermediate Similarity	NPD6336	Discontinued
0.7143	Intermediate Similarity	NPD5141	Approved
0.7121	Intermediate Similarity	NPD7319	Approved
0.7109	Intermediate Similarity	NPD6016	Approved
0.7109	Intermediate Similarity	NPD6015	Approved
0.7107	Intermediate Similarity	NPD6686	Approved
0.7099	Intermediate Similarity	NPD8293	Discontinued
0.7094	Intermediate Similarity	NPD5285	Approved
0.7094	Intermediate Similarity	NPD4696	Approved
0.7094	Intermediate Similarity	NPD5286	Approved
0.7087	Intermediate Similarity	NPD7516	Approved
0.7073	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6083	Phase 2
0.7069	Intermediate Similarity	NPD6084	Phase 2
0.7069	Intermediate Similarity	NPD4755	Approved
0.7054	Intermediate Similarity	NPD5988	Approved
0.7008	Intermediate Similarity	NPD7327	Approved
0.7008	Intermediate Similarity	NPD7328	Approved
0.7	Intermediate Similarity	NPD8328	Phase 3
0.6992	Remote Similarity	NPD4634	Approved
0.6991	Remote Similarity	NPD6698	Approved
0.6991	Remote Similarity	NPD46	Approved
0.6984	Remote Similarity	NPD6274	Approved
0.6975	Remote Similarity	NPD4633	Approved
0.6975	Remote Similarity	NPD5224	Approved
0.6975	Remote Similarity	NPD5225	Approved
0.6975	Remote Similarity	NPD5226	Approved
0.6953	Remote Similarity	NPD7100	Approved
0.6953	Remote Similarity	NPD7101	Approved
0.6949	Remote Similarity	NPD4700	Approved
0.6917	Remote Similarity	NPD5175	Approved
0.6917	Remote Similarity	NPD5174	Approved
0.6897	Remote Similarity	NPD5695	Phase 3
0.6891	Remote Similarity	NPD5223	Approved
0.688	Remote Similarity	NPD6053	Discontinued
0.6875	Remote Similarity	NPD6335	Approved
0.687	Remote Similarity	NPD6399	Phase 3
0.6864	Remote Similarity	NPD5696	Approved
0.6847	Remote Similarity	NPD1696	Phase 3
0.6846	Remote Similarity	NPD6921	Approved
0.6829	Remote Similarity	NPD4730	Approved
0.6829	Remote Similarity	NPD4729	Approved
0.681	Remote Similarity	NPD5282	Discontinued
0.6803	Remote Similarity	NPD4768	Approved
0.6803	Remote Similarity	NPD4767	Approved
0.6797	Remote Similarity	NPD6317	Approved
0.678	Remote Similarity	NPD7902	Approved
0.6774	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6412	Phase 2
0.6744	Remote Similarity	NPD6314	Approved
0.6744	Remote Similarity	NPD6313	Approved
0.672	Remote Similarity	NPD5247	Approved
0.672	Remote Similarity	NPD5248	Approved
0.672	Remote Similarity	NPD5251	Approved
0.672	Remote Similarity	NPD5249	Phase 3
0.672	Remote Similarity	NPD5250	Approved
0.6718	Remote Similarity	NPD8335	Approved
0.6718	Remote Similarity	NPD8380	Approved
0.6718	Remote Similarity	NPD6909	Approved
0.6718	Remote Similarity	NPD8378	Approved
0.6718	Remote Similarity	NPD8379	Approved
0.6718	Remote Similarity	NPD8296	Approved
0.6718	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6908	Approved
0.6718	Remote Similarity	NPD8033	Approved
0.6695	Remote Similarity	NPD4697	Phase 3
0.6695	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5222	Approved
0.6695	Remote Similarity	NPD5221	Approved
0.6694	Remote Similarity	NPD7632	Discontinued
0.6694	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD7260	Phase 2
0.6641	Remote Similarity	NPD8377	Approved
0.6641	Remote Similarity	NPD8294	Approved
0.6639	Remote Similarity	NPD5173	Approved
0.6639	Remote Similarity	NPD4754	Approved
0.6638	Remote Similarity	NPD7515	Phase 2
0.6638	Remote Similarity	NPD7983	Approved
0.6638	Remote Similarity	NPD6079	Approved
0.6612	Remote Similarity	NPD1700	Approved
0.661	Remote Similarity	NPD4629	Approved
0.661	Remote Similarity	NPD5210	Approved
0.6609	Remote Similarity	NPD1695	Approved
0.6609	Remote Similarity	NPD4753	Phase 2
0.6609	Remote Similarity	NPD5328	Approved
0.6591	Remote Similarity	NPD7503	Approved
0.6589	Remote Similarity	NPD6868	Approved
0.6581	Remote Similarity	NPD5779	Approved
0.6581	Remote Similarity	NPD4202	Approved
0.6581	Remote Similarity	NPD5778	Approved
0.6562	Remote Similarity	NPD8133	Approved
0.6552	Remote Similarity	NPD7838	Discovery
0.6552	Remote Similarity	NPD5785	Approved
0.6535	Remote Similarity	NPD5216	Approved
0.6535	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5215	Approved
0.6535	Remote Similarity	NPD5217	Approved
0.6525	Remote Similarity	NPD7900	Approved
0.6525	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5737	Approved
0.6522	Remote Similarity	NPD6672	Approved
0.6496	Remote Similarity	NPD7637	Suspended
0.6491	Remote Similarity	NPD3618	Phase 1
0.6466	Remote Similarity	NPD8517	Approved
0.6466	Remote Similarity	NPD6904	Approved
0.6466	Remote Similarity	NPD8516	Approved
0.6466	Remote Similarity	NPD6673	Approved
0.6466	Remote Similarity	NPD8515	Approved
0.6466	Remote Similarity	NPD8513	Phase 3
0.6466	Remote Similarity	NPD6080	Approved
0.6457	Remote Similarity	NPD5135	Approved
0.6457	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5169	Approved
0.6446	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7524	Approved
0.6406	Remote Similarity	NPD5127	Approved
0.6404	Remote Similarity	NPD1694	Approved
0.6404	Remote Similarity	NPD5363	Approved
0.6387	Remote Similarity	NPD6001	Approved
0.6372	Remote Similarity	NPD5362	Discontinued
0.6372	Remote Similarity	NPD7154	Phase 3
0.6372	Remote Similarity	NPD6110	Phase 1
0.6357	Remote Similarity	NPD6845	Suspended
0.6356	Remote Similarity	NPD5281	Approved
0.6356	Remote Similarity	NPD6050	Approved
0.6356	Remote Similarity	NPD8035	Phase 2
0.6356	Remote Similarity	NPD8034	Phase 2
0.6356	Remote Similarity	NPD5693	Phase 1
0.6356	Remote Similarity	NPD5284	Approved
0.6348	Remote Similarity	NPD7146	Approved
0.6348	Remote Similarity	NPD6684	Approved
0.6348	Remote Similarity	NPD7334	Approved
0.6348	Remote Similarity	NPD7521	Approved
0.6348	Remote Similarity	NPD5330	Approved
0.6348	Remote Similarity	NPD6409	Approved
0.6316	Remote Similarity	NPD4786	Approved
0.6316	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD3573	Approved
0.6283	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5692	Phase 3
0.6261	Remote Similarity	NPD5329	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