NPASS Compound

Structure

NPC472759 OpenBabel07101719252D 40 43 0 0 1 0 0 0 0 0999 V2000 -7.7410 -3.6162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6352 -2.4609 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 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 -6.8825 -3.1033 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 -6.0091 -3.5903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1507 -3.0774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2773 -3.5644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4188 -3.0515 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 0.9033 -2.4868 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 -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 -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 -1.4452 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 -1.7019 -2.0257 0.0000 C 0 0 0 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 -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 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 -2.5753 -1.5387 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 -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 7 1 0 0 0 0 2 8 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 31 1 0 0 0 0 6 31 1 0 0 0 0 7 9 1 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 13 15 2 0 0 0 0 14 27 1 0 0 0 0 15 26 1 0 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 17 22 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 22 1 0 0 0 0 19 34 1 0 0 0 0 20 28 1 0 0 0 0 21 30 1 0 0 0 0 21 32 1 1 0 0 0 23 17 1 6 0 0 0 23 24 1 0 0 0 0 23 28 1 0 0 0 0 24 32 1 6 0 0 0 25 29 1 0 0 0 0 25 32 1 1 0 0 0 26 35 2 0 0 0 0 26 39 1 0 0 0 0 27 36 2 0 0 0 0 27 40 1 0 0 0 0 28 37 2 0 0 0 0 29 31 1 0 0 0 0 29 33 1 6 0 0 0 30 33 1 6 0 0 0 30 39 1 0 0 0 0 31 33 1 0 0 0 0 32 38 1 1 0 0 0 33 40 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	552.31
Volume:	585.538
LogP:	4.33
LogD:	3.418
LogS:	-4.803
# Rotatable Bonds:	11
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.183
Synthetic Accessibility Score:	5.416
Fsp3:	0.606
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.668
MDCK Permeability:	1.541812889627181e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.28

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.642
Plasma Protein Binding (PPB):	84.9442367553711%
Volume Distribution (VD):	0.611
Pgp-substrate:	7.625399589538574%

ADMET: Metabolism

CYP1A2-inhibitor:	0.142
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.744
CYP2C19-substrate:	0.618
CYP2C9-inhibitor:	0.905
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.708
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.938
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	5.692
Half-life (T1/2):	0.381

ADMET: Toxicity

hERG Blockers:	0.763
Human Hepatotoxicity (H-HT):	0.986
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.826
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.657
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC472759

Natural Product ID:	NPC472759
*Common Name:**	NOBRZUCGXCJOPI-CZBHJNBTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NOBRZUCGXCJOPI-CZBHJNBTSA-N
Standard InCHI:	InChI=1S/C33H44O7/c1-7-9-10-11-12-13-15-26(35)39-30-21(4)32(38)24-16-20(3)28(37)23(24)17-22(19-34)18-25(32)29-31(5,6)33(29,30)40-27(36)14-8-2/h9-13,15-16,18,21,23-25,29-30,34,38H,7-8,14,17,19H2,1-6H3/b10-9+,12-11+,15-13-/t21-,23-,24-,25+,29-,30-,32+,33-/m1/s1
SMILES:	CC/C=C/C=C/C=CC(=O)O[C@@H]1[C@@H](C)[C@]2(O)[C@@H]3C=C(C(=O)[C@@H]3CC(=C[C@H]2[C@H]2[C@]1(OC(=O)CCC)C2(C)C)CO)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582006
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

*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
NPO33329	stillingia lineata	Species	Euphorbiaceae	Eukaryota	Leaves	Langevin, La Reunion, France	2009-Nov	PMID[25946116]

☑ 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	5
Others	9

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Organism	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Inhibition	<	40.0	%	PMID[530011]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	<	40.0	%	PMID[530011]
NPT306	Cell Line	PC-3	Homo sapiens	Inhibition	<	40.0	%	PMID[530011]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	7100.0	nM	PMID[530011]
NPT25	Cell Line	MT4	Homo sapiens	CC50	=	8400.0	nM	PMID[530011]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	233.0	nM	PMID[530011]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	174.0	nM	PMID[530011]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	36.0	n.a.	PMID[530011]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	33.0	n.a.	PMID[530011]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	1400.0	nM	PMID[530011]
NPT338	Organism	Sindbis virus	Sindbis virus	EC50	=	5000.0	nM	PMID[530011]
NPT856	Organism	Semliki forest virus	Semliki forest virus	EC50	>	177000.0	nM	PMID[530011]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	5.1	n.a.	PMID[530011]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	1.4	n.a.	PMID[530011]

☑ 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 NPC472759 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	244
0.1-0.2	1290
0.2-0.3	3861
0.3-0.4	6351
0.4-0.5	13434
0.5-0.6	9805
0.6-0.7	6169
0.7-0.8	1342
0.8-0.85	82
0.85-0.9	46
0.9-0.95	48
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC329080
0.9909	High Similarity	NPC156745
0.9909	High Similarity	NPC236918
0.982	High Similarity	NPC475885
0.9727	High Similarity	NPC10721
0.9649	High Similarity	NPC145238
0.964	High Similarity	NPC146280
0.964	High Similarity	NPC124676
0.9636	High Similarity	NPC154363
0.9636	High Similarity	NPC471127
0.9636	High Similarity	NPC234858
0.9455	High Similarity	NPC472757
0.9386	High Similarity	NPC52839
0.9369	High Similarity	NPC472400
0.9304	High Similarity	NPC257017
0.9304	High Similarity	NPC162009
0.9298	High Similarity	NPC157252
0.9298	High Similarity	NPC471128
0.9298	High Similarity	NPC145182
0.9298	High Similarity	NPC471126
0.9298	High Similarity	NPC185876
0.9298	High Similarity	NPC19336
0.9292	High Similarity	NPC472760
0.9211	High Similarity	NPC275696
0.9211	High Similarity	NPC471108
0.9211	High Similarity	NPC22628
0.9211	High Similarity	NPC255081
0.9211	High Similarity	NPC5991
0.9211	High Similarity	NPC180640
0.9211	High Similarity	NPC5989
0.9123	High Similarity	NPC171905
0.9123	High Similarity	NPC471125
0.9123	High Similarity	NPC472397
0.9123	High Similarity	NPC472758
0.906	High Similarity	NPC472399
0.9035	High Similarity	NPC153651
0.9035	High Similarity	NPC156252
0.8974	High Similarity	NPC19464
0.8938	High Similarity	NPC71889
0.8889	High Similarity	NPC472401
0.886	High Similarity	NPC474872
0.885	High Similarity	NPC221511
0.885	High Similarity	NPC89227
0.885	High Similarity	NPC151216
0.885	High Similarity	NPC101825
0.885	High Similarity	NPC215643
0.885	High Similarity	NPC17138
0.885	High Similarity	NPC265499
0.885	High Similarity	NPC170212
0.8833	High Similarity	NPC471940
0.8772	High Similarity	NPC474937
0.8761	High Similarity	NPC174471
0.8761	High Similarity	NPC474871
0.8761	High Similarity	NPC475937
0.8761	High Similarity	NPC96739
0.8761	High Similarity	NPC260786
0.8761	High Similarity	NPC158523
0.876	High Similarity	NPC236999
0.875	High Similarity	NPC471939
0.8684	High Similarity	NPC475391
0.8673	High Similarity	NPC153036
0.8667	High Similarity	NPC473919
0.8667	High Similarity	NPC473709
0.8607	High Similarity	NPC270109
0.8583	High Similarity	NPC473802
0.8559	High Similarity	NPC472667
0.848	Intermediate Similarity	NPC476111
0.8448	Intermediate Similarity	NPC477091
0.8443	Intermediate Similarity	NPC222307
0.8421	Intermediate Similarity	NPC273433
0.8421	Intermediate Similarity	NPC163004
0.8403	Intermediate Similarity	NPC470186
0.8376	Intermediate Similarity	NPC133677
0.8376	Intermediate Similarity	NPC138303
0.8376	Intermediate Similarity	NPC67290
0.8333	Intermediate Similarity	NPC143755
0.8293	Intermediate Similarity	NPC293112
0.8291	Intermediate Similarity	NPC469463
0.8291	Intermediate Similarity	NPC469454
0.8291	Intermediate Similarity	NPC46269
0.8291	Intermediate Similarity	NPC106395
0.8291	Intermediate Similarity	NPC469496
0.8271	Intermediate Similarity	NPC140021
0.8268	Intermediate Similarity	NPC471137
0.8268	Intermediate Similarity	NPC182266
0.8268	Intermediate Similarity	NPC100017
0.8268	Intermediate Similarity	NPC475500
0.8268	Intermediate Similarity	NPC475154
0.8268	Intermediate Similarity	NPC473548
0.8268	Intermediate Similarity	NPC471136
0.8268	Intermediate Similarity	NPC223356
0.8264	Intermediate Similarity	NPC310511
0.8254	Intermediate Similarity	NPC90814
0.8254	Intermediate Similarity	NPC189393
0.8246	Intermediate Similarity	NPC187435
0.8246	Intermediate Similarity	NPC67321
0.8235	Intermediate Similarity	NPC469684
0.822	Intermediate Similarity	NPC73314
0.8205	Intermediate Similarity	NPC138757
0.8205	Intermediate Similarity	NPC76550
0.8205	Intermediate Similarity	NPC123855
0.8182	Intermediate Similarity	NPC475003
0.8174	Intermediate Similarity	NPC102843
0.8167	Intermediate Similarity	NPC284707
0.816	Intermediate Similarity	NPC470850
0.8151	Intermediate Similarity	NPC179626
0.8151	Intermediate Similarity	NPC470793
0.8145	Intermediate Similarity	NPC473635
0.814	Intermediate Similarity	NPC68282
0.8136	Intermediate Similarity	NPC471204
0.813	Intermediate Similarity	NPC469789
0.813	Intermediate Similarity	NPC11895
0.812	Intermediate Similarity	NPC474846
0.812	Intermediate Similarity	NPC469655
0.812	Intermediate Similarity	NPC304180
0.812	Intermediate Similarity	NPC469656
0.812	Intermediate Similarity	NPC179798
0.8115	Intermediate Similarity	NPC67569
0.811	Intermediate Similarity	NPC475139
0.811	Intermediate Similarity	NPC180902
0.811	Intermediate Similarity	NPC473485
0.811	Intermediate Similarity	NPC474508
0.8099	Intermediate Similarity	NPC469380
0.8095	Intermediate Similarity	NPC470851
0.8095	Intermediate Similarity	NPC104382
0.8087	Intermediate Similarity	NPC143609
0.8083	Intermediate Similarity	NPC53396
0.8083	Intermediate Similarity	NPC474518
0.8083	Intermediate Similarity	NPC98249
0.807	Intermediate Similarity	NPC118911
0.8065	Intermediate Similarity	NPC81736
0.8065	Intermediate Similarity	NPC172154
0.8053	Intermediate Similarity	NPC478156
0.8053	Intermediate Similarity	NPC476081
0.8051	Intermediate Similarity	NPC472002
0.8051	Intermediate Similarity	NPC234042
0.8051	Intermediate Similarity	NPC470063
0.8051	Intermediate Similarity	NPC152117
0.8049	Intermediate Similarity	NPC23786
0.8049	Intermediate Similarity	NPC170538
0.8049	Intermediate Similarity	NPC470265
0.8034	Intermediate Similarity	NPC257240
0.8034	Intermediate Similarity	NPC5103
0.8034	Intermediate Similarity	NPC472214
0.8034	Intermediate Similarity	NPC253906
0.8034	Intermediate Similarity	NPC472215
0.8033	Intermediate Similarity	NPC48692
0.8033	Intermediate Similarity	NPC4548
0.8031	Intermediate Similarity	NPC251564
0.8031	Intermediate Similarity	NPC475606
0.8031	Intermediate Similarity	NPC471170
0.8031	Intermediate Similarity	NPC475314
0.8031	Intermediate Similarity	NPC477189
0.8017	Intermediate Similarity	NPC306265
0.8	Intermediate Similarity	NPC111952
0.8	Intermediate Similarity	NPC34768
0.8	Intermediate Similarity	NPC243902
0.8	Intermediate Similarity	NPC471816
0.8	Intermediate Similarity	NPC176840
0.7984	Intermediate Similarity	NPC473979
0.7983	Intermediate Similarity	NPC474271
0.7983	Intermediate Similarity	NPC56448
0.7983	Intermediate Similarity	NPC25909
0.7982	Intermediate Similarity	NPC23584
0.7966	Intermediate Similarity	NPC470076
0.7966	Intermediate Similarity	NPC188738
0.7953	Intermediate Similarity	NPC175186
0.7953	Intermediate Similarity	NPC162495
0.7953	Intermediate Similarity	NPC231529
0.7951	Intermediate Similarity	NPC77689
0.7951	Intermediate Similarity	NPC473636
0.7951	Intermediate Similarity	NPC475041
0.7951	Intermediate Similarity	NPC473839
0.7951	Intermediate Similarity	NPC211093
0.7949	Intermediate Similarity	NPC475586
0.7949	Intermediate Similarity	NPC469370
0.7949	Intermediate Similarity	NPC47951
0.7949	Intermediate Similarity	NPC472216
0.7949	Intermediate Similarity	NPC5475
0.7949	Intermediate Similarity	NPC475065
0.7949	Intermediate Similarity	NPC137911
0.7949	Intermediate Similarity	NPC284828
0.7949	Intermediate Similarity	NPC173905
0.7949	Intermediate Similarity	NPC228477
0.7934	Intermediate Similarity	NPC470493
0.7934	Intermediate Similarity	NPC183580
0.7934	Intermediate Similarity	NPC312824
0.7934	Intermediate Similarity	NPC475323
0.7934	Intermediate Similarity	NPC284068
0.7934	Intermediate Similarity	NPC473656
0.7934	Intermediate Similarity	NPC23046
0.7928	Intermediate Similarity	NPC284518
0.792	Intermediate Similarity	NPC8369
0.7917	Intermediate Similarity	NPC238667
0.7913	Intermediate Similarity	NPC239162
0.7899	Intermediate Similarity	NPC269530
0.7899	Intermediate Similarity	NPC476801
0.7899	Intermediate Similarity	NPC236217
0.7895	Intermediate Similarity	NPC137430
0.7895	Intermediate Similarity	NPC162973

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 NPC472759 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	1545
0.2-0.3	3504
0.3-0.4	2438
0.4-0.5	945
0.5-0.6	354
0.6-0.7	142
0.7-0.8	11
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
0.8034	Intermediate Similarity	NPD6371	Approved
0.7876	Intermediate Similarity	NPD6648	Approved
0.7807	Intermediate Similarity	NPD5344	Discontinued
0.7787	Intermediate Similarity	NPD7115	Discovery
0.7647	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD4225	Approved
0.7317	Intermediate Similarity	NPD8297	Approved
0.7265	Intermediate Similarity	NPD7639	Approved
0.7265	Intermediate Similarity	NPD7640	Approved
0.7179	Intermediate Similarity	NPD7638	Approved
0.7168	Intermediate Similarity	NPD7838	Discovery
0.7154	Intermediate Similarity	NPD7604	Phase 2
0.7131	Intermediate Similarity	NPD6686	Approved
0.7131	Intermediate Similarity	NPD6899	Approved
0.7131	Intermediate Similarity	NPD6881	Approved
0.712	Intermediate Similarity	NPD4632	Approved
0.7097	Intermediate Similarity	NPD6650	Approved
0.7097	Intermediate Similarity	NPD8130	Phase 1
0.7097	Intermediate Similarity	NPD6649	Approved
0.7069	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6319	Approved
0.7049	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5697	Approved
0.7045	Intermediate Similarity	NPD7507	Approved
0.7034	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD46	Approved
0.7018	Intermediate Similarity	NPD6698	Approved
0.7016	Intermediate Similarity	NPD7290	Approved
0.7016	Intermediate Similarity	NPD7102	Approved
0.7016	Intermediate Similarity	NPD6883	Approved
0.7015	Intermediate Similarity	NPD7319	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD8513	Phase 3
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD8517	Approved
0.6977	Remote Similarity	NPD7516	Approved
0.697	Remote Similarity	NPD7492	Approved
0.6967	Remote Similarity	NPD5739	Approved
0.6967	Remote Similarity	NPD6008	Approved
0.6967	Remote Similarity	NPD7128	Approved
0.6967	Remote Similarity	NPD6675	Approved
0.6967	Remote Similarity	NPD6402	Approved
0.696	Remote Similarity	NPD6869	Approved
0.696	Remote Similarity	NPD6847	Approved
0.696	Remote Similarity	NPD6617	Approved
0.6957	Remote Similarity	NPD7983	Approved
0.6953	Remote Similarity	NPD6009	Approved
0.694	Remote Similarity	NPD7736	Approved
0.6935	Remote Similarity	NPD6013	Approved
0.6935	Remote Similarity	NPD6012	Approved
0.6935	Remote Similarity	NPD6373	Approved
0.6935	Remote Similarity	NPD6372	Approved
0.6935	Remote Similarity	NPD6014	Approved
0.6923	Remote Similarity	NPD6054	Approved
0.6917	Remote Similarity	NPD6616	Approved
0.6905	Remote Similarity	NPD6053	Discontinued
0.6905	Remote Similarity	NPD6882	Approved
0.6899	Remote Similarity	NPD7327	Approved
0.6899	Remote Similarity	NPD7328	Approved
0.6897	Remote Similarity	NPD5779	Approved
0.6897	Remote Similarity	NPD5778	Approved
0.687	Remote Similarity	NPD7503	Approved
0.687	Remote Similarity	NPD5983	Phase 2
0.6866	Remote Similarity	NPD7078	Approved
0.686	Remote Similarity	NPD5211	Phase 2
0.6855	Remote Similarity	NPD7320	Approved
0.6855	Remote Similarity	NPD6011	Approved
0.6818	Remote Similarity	NPD6370	Approved
0.681	Remote Similarity	NPD7637	Suspended
0.6807	Remote Similarity	NPD7902	Approved
0.6791	Remote Similarity	NPD6336	Discontinued
0.6788	Remote Similarity	NPD7260	Phase 2
0.6774	Remote Similarity	NPD5701	Approved
0.6752	Remote Similarity	NPD6399	Phase 3
0.6748	Remote Similarity	NPD5141	Approved
0.6742	Remote Similarity	NPD8380	Approved
0.6742	Remote Similarity	NPD8335	Approved
0.6742	Remote Similarity	NPD6016	Approved
0.6742	Remote Similarity	NPD8379	Approved
0.6742	Remote Similarity	NPD8296	Approved
0.6742	Remote Similarity	NPD8033	Approved
0.6742	Remote Similarity	NPD6015	Approved
0.6742	Remote Similarity	NPD6921	Approved
0.6742	Remote Similarity	NPD8378	Approved
0.6741	Remote Similarity	NPD8293	Discontinued
0.6741	Remote Similarity	NPD8074	Phase 3
0.6726	Remote Similarity	NPD1694	Approved
0.6726	Remote Similarity	NPD1696	Phase 3
0.6724	Remote Similarity	NPD5785	Approved
0.6721	Remote Similarity	NPD7632	Discontinued
0.6695	Remote Similarity	NPD7748	Approved
0.6694	Remote Similarity	NPD5286	Approved
0.6694	Remote Similarity	NPD5285	Approved
0.6694	Remote Similarity	NPD4696	Approved
0.6692	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6079	Approved
0.6642	Remote Similarity	NPD8328	Phase 3
0.6638	Remote Similarity	NPD1695	Approved
0.6614	Remote Similarity	NPD4634	Approved
0.6609	Remote Similarity	NPD7524	Approved
0.6591	Remote Similarity	NPD7100	Approved
0.6591	Remote Similarity	NPD7101	Approved
0.6589	Remote Similarity	NPD8133	Approved
0.6585	Remote Similarity	NPD5224	Approved
0.6585	Remote Similarity	NPD5226	Approved
0.6585	Remote Similarity	NPD4633	Approved
0.6585	Remote Similarity	NPD5225	Approved
0.6562	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7900	Approved
0.6555	Remote Similarity	NPD5282	Discontinued
0.6532	Remote Similarity	NPD5174	Approved
0.6532	Remote Similarity	NPD5175	Approved
0.6529	Remote Similarity	NPD6084	Phase 2
0.6529	Remote Similarity	NPD6083	Phase 2
0.6529	Remote Similarity	NPD4755	Approved
0.6525	Remote Similarity	NPD6411	Approved
0.6525	Remote Similarity	NPD7515	Phase 2
0.6525	Remote Similarity	NPD5284	Approved
0.6525	Remote Similarity	NPD5281	Approved
0.6515	Remote Similarity	NPD6335	Approved
0.6508	Remote Similarity	NPD6412	Phase 2
0.6504	Remote Similarity	NPD5223	Approved
0.65	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD5328	Approved
0.6491	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6274	Approved
0.646	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5209	Approved
0.6446	Remote Similarity	NPD5222	Approved
0.6446	Remote Similarity	NPD5221	Approved
0.6446	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6317	Approved
0.6435	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD4700	Approved
0.6404	Remote Similarity	NPD6695	Phase 3
0.6393	Remote Similarity	NPD5173	Approved
0.6391	Remote Similarity	NPD6313	Approved
0.6391	Remote Similarity	NPD6314	Approved
0.6387	Remote Similarity	NPD8035	Phase 2
0.6387	Remote Similarity	NPD8034	Phase 2
0.6383	Remote Similarity	NPD6845	Suspended
0.6379	Remote Similarity	NPD3618	Phase 1
0.637	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6868	Approved
0.6364	Remote Similarity	NPD5695	Phase 3
0.6356	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6101	Approved
0.6341	Remote Similarity	NPD5696	Approved
0.6333	Remote Similarity	NPD4202	Approved
0.6328	Remote Similarity	NPD4730	Approved
0.6328	Remote Similarity	NPD4729	Approved
0.6325	Remote Similarity	NPD3573	Approved
0.6325	Remote Similarity	NPD7750	Discontinued
0.6316	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7839	Suspended
0.6311	Remote Similarity	NPD4697	Phase 3
0.6293	Remote Similarity	NPD5363	Approved
0.6283	Remote Similarity	NPD7332	Phase 2
0.6261	Remote Similarity	NPD7154	Phase 3
0.6261	Remote Similarity	NPD5362	Discontinued
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD6908	Approved
0.6231	Remote Similarity	NPD5250	Approved
0.6231	Remote Similarity	NPD5247	Approved
0.6231	Remote Similarity	NPD5251	Approved
0.6231	Remote Similarity	NPD5249	Phase 3
0.6231	Remote Similarity	NPD5248	Approved
0.623	Remote Similarity	NPD4629	Approved
0.623	Remote Similarity	NPD5210	Approved
0.6228	Remote Similarity	NPD6902	Approved
0.6214	Remote Similarity	NPD6033	Approved
0.6207	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4786	Approved
0.6202	Remote Similarity	NPD5128	Approved
0.6187	Remote Similarity	NPD8273	Phase 1
0.6184	Remote Similarity	NPD7236	Approved
0.6183	Remote Similarity	NPD5215	Approved
0.6183	Remote Similarity	NPD5217	Approved
0.6183	Remote Similarity	NPD5216	Approved
0.6176	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD4767	Approved
0.6172	Remote Similarity	NPD4768	Approved
0.6167	Remote Similarity	NPD5207	Approved
0.6159	Remote Similarity	NPD7830	Approved
0.6159	Remote Similarity	NPD7829	Approved
0.6148	Remote Similarity	NPD6001	Approved
0.6142	Remote Similarity	NPD4754	Approved
0.614	Remote Similarity	NPD6930	Phase 2
0.614	Remote Similarity	NPD7514	Phase 3
0.614	Remote Similarity	NPD6931	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