NPASS Compound

Structure

NPC475323 OpenBabel07101718242D 36 41 0 0 1 0 0 0 0 0999 V2000 -8.0472 -1.3191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6385 -1.3850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2653 -1.5210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5425 -2.2121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1960 -1.0658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9446 -3.4575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9501 -3.3530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0943 -2.4983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8806 -2.2758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6082 -0.8748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7422 -0.3748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3835 -1.9577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1695 1.1182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0943 -0.2513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3780 -2.0623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3295 -2.3361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3514 -2.5440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7422 -2.3748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8762 -1.8748 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9768 -2.8713 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3145 -1.3748 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6034 0.2172 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1786 0.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9986 -3.0792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5860 -3.0404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3054 -1.2406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6082 -1.8748 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8762 -0.8748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8806 -0.4739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5125 1.7067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6896 -4.0303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4995 -3.4472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3128 -1.7011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7199 -3.5404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4840 -0.2567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 13 23 1 0 0 0 0 14 28 1 0 0 0 0 15 25 1 0 0 0 0 16 2 1 1 0 0 0 16 17 1 0 0 0 0 16 24 1 0 0 0 0 17 27 1 6 0 0 0 18 19 1 0 0 0 0 18 27 1 0 0 0 0 19 28 1 1 0 0 0 20 24 1 1 0 0 0 20 34 1 0 0 0 0 21 26 1 0 0 0 0 21 29 1 6 0 0 0 22 29 1 1 0 0 0 22 35 1 0 0 0 0 23 30 2 0 0 0 0 23 36 1 0 0 0 0 24 31 1 6 0 0 0 25 32 2 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 5 1 6 0 0 0 28 33 1 1 0 0 0 29 14 1 6 0 0 0 29 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.28
Volume:	509.787
LogP:	4.192
LogD:	2.925
LogS:	-4.493
# Rotatable Bonds:	3
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	6.085
Fsp3:	0.759
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:	-5.092
MDCK Permeability:	1.52952634380199e-05
Pgp-inhibitor:	0.075
Pgp-substrate:	0.902
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.474
Plasma Protein Binding (PPB):	90.03028106689453%
Volume Distribution (VD):	1.533
Pgp-substrate:	7.450255870819092%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.276
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.422
CYP2C9-inhibitor:	0.102
CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.192
CYP3A4-inhibitor:	0.661
CYP3A4-substrate:	0.263

ADMET: Excretion

Clearance (CL):	9.662
Half-life (T1/2):	0.178

ADMET: Toxicity

hERG Blockers:	0.152
Human Hepatotoxicity (H-HT):	0.513
Drug-inuced Liver Injury (DILI):	0.082
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.886
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.177
Carcinogencity:	0.749
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC475323

Natural Product ID:	NPC475323
*Common Name:**	Kadcoccilactone E
IUPAC Name:	n.a.
Synonyms:	Kadcoccilactone E
Standard InCHIKey:	NBZDXWQJHKPYOE-HNBWECBUSA-N
Standard InCHI:	InChI=1S/C29H40O7/c1-15-12-20(34-25(15)32)24(31)16(2)17-6-7-18-19-8-9-21-26(3,4)35-22-13-23(30)36-29(21,22)14-28(19,33)11-10-27(17,18)5/h7,12,16-17,19-22,24,31,33H,6,8-11,13-14H2,1-5H3/t16-,17+,19-,20-,21-,22+,24-,27+,28-,29+/m0/s1
SMILES:	CC1=CC(OC1=O)C(C(C)C2CC=C3C2(CCC4(C3CCC5C(OC6C5(C4)OC(=O)C6)(C)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503463
PubChem CID:	24970759
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001816] Furofurans

*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
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18027905]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271558]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	roots	n.a.	n.a.	PMID[18491866]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590312]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24299567]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214125]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[27704807]
NPO912	Kadsura coccinea	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO912	Kadsura coccinea	Species	Schisandraceae	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	1

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[486021]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[486021]
NPT81	Cell Line	A549	Homo sapiens	IC	>	100.0	ug ml-1	PMID[486021]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[486021]

☑ 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 NPC475323 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	235
0.1-0.2	1302
0.2-0.3	4420
0.3-0.4	8209
0.4-0.5	13531
0.5-0.6	7105
0.6-0.7	6142
0.7-0.8	1714
0.8-0.85	31
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9298	High Similarity	NPC129992
0.9279	High Similarity	NPC473656
0.913	High Similarity	NPC469352
0.9027	High Similarity	NPC475372
0.9009	High Similarity	NPC473535
0.8947	High Similarity	NPC312536
0.8611	High Similarity	NPC86077
0.8595	High Similarity	NPC475371
0.8584	High Similarity	NPC470063
0.8455	Intermediate Similarity	NPC146731
0.8455	Intermediate Similarity	NPC296950
0.8435	Intermediate Similarity	NPC123117
0.8305	Intermediate Similarity	NPC469380
0.8304	Intermediate Similarity	NPC67321
0.8304	Intermediate Similarity	NPC187435
0.8291	Intermediate Similarity	NPC284068
0.8288	Intermediate Similarity	NPC203659
0.8261	Intermediate Similarity	NPC269530
0.8246	Intermediate Similarity	NPC475134
0.8246	Intermediate Similarity	NPC235014
0.8246	Intermediate Similarity	NPC475563
0.822	Intermediate Similarity	NPC146280
0.822	Intermediate Similarity	NPC124676
0.8214	Intermediate Similarity	NPC475217
0.8214	Intermediate Similarity	NPC472655
0.8205	Intermediate Similarity	NPC471127
0.8205	Intermediate Similarity	NPC154363
0.8205	Intermediate Similarity	NPC234858
0.8198	Intermediate Similarity	NPC69171
0.8198	Intermediate Similarity	NPC159533
0.8198	Intermediate Similarity	NPC474165
0.8198	Intermediate Similarity	NPC110989
0.8174	Intermediate Similarity	NPC473921
0.8174	Intermediate Similarity	NPC475668
0.8174	Intermediate Similarity	NPC475480
0.8167	Intermediate Similarity	NPC67569
0.816	Intermediate Similarity	NPC34963
0.8158	Intermediate Similarity	NPC42662
0.8158	Intermediate Similarity	NPC273433
0.8145	Intermediate Similarity	NPC35109
0.8142	Intermediate Similarity	NPC26617
0.8136	Intermediate Similarity	NPC10721
0.8136	Intermediate Similarity	NPC475238
0.8131	Intermediate Similarity	NPC477131
0.812	Intermediate Similarity	NPC471380
0.812	Intermediate Similarity	NPC472400
0.8115	Intermediate Similarity	NPC8369
0.8108	Intermediate Similarity	NPC225353
0.8108	Intermediate Similarity	NPC476081
0.8108	Intermediate Similarity	NPC183571
0.8108	Intermediate Similarity	NPC474709
0.8103	Intermediate Similarity	NPC23967
0.8099	Intermediate Similarity	NPC287236
0.8099	Intermediate Similarity	NPC23786
0.8099	Intermediate Similarity	NPC470265
0.8095	Intermediate Similarity	NPC58029
0.8095	Intermediate Similarity	NPC469673
0.8087	Intermediate Similarity	NPC179642
0.8087	Intermediate Similarity	NPC475463
0.8087	Intermediate Similarity	NPC257240
0.8087	Intermediate Similarity	NPC5103
0.8083	Intermediate Similarity	NPC475885
0.808	Intermediate Similarity	NPC196921
0.808	Intermediate Similarity	NPC220757
0.808	Intermediate Similarity	NPC241935
0.808	Intermediate Similarity	NPC279478
0.807	Intermediate Similarity	NPC255082
0.807	Intermediate Similarity	NPC94377
0.807	Intermediate Similarity	NPC306265
0.8067	Intermediate Similarity	NPC161060
0.8067	Intermediate Similarity	NPC288679
0.8065	Intermediate Similarity	NPC236999
0.8065	Intermediate Similarity	NPC470850
0.8053	Intermediate Similarity	NPC243998
0.8053	Intermediate Similarity	NPC173172
0.8053	Intermediate Similarity	NPC475414
0.8051	Intermediate Similarity	NPC138372
0.8051	Intermediate Similarity	NPC106228
0.8036	Intermediate Similarity	NPC474775
0.8034	Intermediate Similarity	NPC472757
0.8034	Intermediate Similarity	NPC477126
0.8034	Intermediate Similarity	NPC469454
0.8034	Intermediate Similarity	NPC469463
0.8034	Intermediate Similarity	NPC469496
0.8034	Intermediate Similarity	NPC470120
0.8033	Intermediate Similarity	NPC473802
0.8033	Intermediate Similarity	NPC472399
0.8033	Intermediate Similarity	NPC469382
0.8033	Intermediate Similarity	NPC469789
0.8031	Intermediate Similarity	NPC476823
0.8018	Intermediate Similarity	NPC308824
0.8	Intermediate Similarity	NPC236918
0.8	Intermediate Similarity	NPC231529
0.8	Intermediate Similarity	NPC473593
0.8	Intermediate Similarity	NPC477102
0.8	Intermediate Similarity	NPC156745
0.8	Intermediate Similarity	NPC222303
0.7984	Intermediate Similarity	NPC298841
0.7983	Intermediate Similarity	NPC36754
0.7983	Intermediate Similarity	NPC312824
0.7983	Intermediate Similarity	NPC470493
0.7983	Intermediate Similarity	NPC183580
0.7982	Intermediate Similarity	NPC475176
0.7967	Intermediate Similarity	NPC75856
0.7967	Intermediate Similarity	NPC469379
0.7967	Intermediate Similarity	NPC473919
0.7967	Intermediate Similarity	NPC473709
0.7967	Intermediate Similarity	NPC86346
0.7967	Intermediate Similarity	NPC144625
0.7966	Intermediate Similarity	NPC90472
0.7965	Intermediate Similarity	NPC294259
0.7965	Intermediate Similarity	NPC100487
0.7951	Intermediate Similarity	NPC257017
0.7951	Intermediate Similarity	NPC162009
0.7949	Intermediate Similarity	NPC473877
0.7949	Intermediate Similarity	NPC236217
0.7944	Intermediate Similarity	NPC131209
0.7944	Intermediate Similarity	NPC133698
0.7934	Intermediate Similarity	NPC145182
0.7934	Intermediate Similarity	NPC157252
0.7934	Intermediate Similarity	NPC4548
0.7934	Intermediate Similarity	NPC471126
0.7934	Intermediate Similarity	NPC472004
0.7934	Intermediate Similarity	NPC472759
0.7934	Intermediate Similarity	NPC329080
0.7934	Intermediate Similarity	NPC143755
0.7934	Intermediate Similarity	NPC471128
0.7931	Intermediate Similarity	NPC29133
0.7931	Intermediate Similarity	NPC48305
0.7931	Intermediate Similarity	NPC477103
0.7931	Intermediate Similarity	NPC474923
0.7928	Intermediate Similarity	NPC474718
0.7928	Intermediate Similarity	NPC47024
0.7917	Intermediate Similarity	NPC186525
0.7917	Intermediate Similarity	NPC106644
0.7917	Intermediate Similarity	NPC50774
0.7917	Intermediate Similarity	NPC709
0.7913	Intermediate Similarity	NPC151393
0.7909	Intermediate Similarity	NPC73911
0.7903	Intermediate Similarity	NPC293112
0.7903	Intermediate Similarity	NPC471939
0.7903	Intermediate Similarity	NPC15095
0.7899	Intermediate Similarity	NPC470075
0.7899	Intermediate Similarity	NPC470793
0.7899	Intermediate Similarity	NPC64318
0.7895	Intermediate Similarity	NPC223450
0.789	Intermediate Similarity	NPC304886
0.7886	Intermediate Similarity	NPC1538
0.7886	Intermediate Similarity	NPC11895
0.7881	Intermediate Similarity	NPC209058
0.7881	Intermediate Similarity	NPC46269
0.7881	Intermediate Similarity	NPC106395
0.7881	Intermediate Similarity	NPC71889
0.7876	Intermediate Similarity	NPC475871
0.7876	Intermediate Similarity	NPC36688
0.7876	Intermediate Similarity	NPC168575
0.7876	Intermediate Similarity	NPC156681
0.7876	Intermediate Similarity	NPC475945
0.7876	Intermediate Similarity	NPC120321
0.7876	Intermediate Similarity	NPC112009
0.7874	Intermediate Similarity	NPC180902
0.7874	Intermediate Similarity	NPC475139
0.7869	Intermediate Similarity	NPC52839
0.7869	Intermediate Similarity	NPC472401
0.7869	Intermediate Similarity	NPC46570
0.7863	Intermediate Similarity	NPC179798
0.7863	Intermediate Similarity	NPC304180
0.7863	Intermediate Similarity	NPC260786
0.7863	Intermediate Similarity	NPC96739
0.7863	Intermediate Similarity	NPC470076
0.7863	Intermediate Similarity	NPC474871
0.7863	Intermediate Similarity	NPC174471
0.7863	Intermediate Similarity	NPC324683
0.7863	Intermediate Similarity	NPC317107
0.7863	Intermediate Similarity	NPC470961
0.7857	Intermediate Similarity	NPC470851
0.7857	Intermediate Similarity	NPC471412
0.7857	Intermediate Similarity	NPC13071
0.7851	Intermediate Similarity	NPC19028
0.7851	Intermediate Similarity	NPC473839
0.7851	Intermediate Similarity	NPC77689
0.7851	Intermediate Similarity	NPC9674
0.7851	Intermediate Similarity	NPC472667
0.7851	Intermediate Similarity	NPC42673
0.7851	Intermediate Similarity	NPC230513
0.7851	Intermediate Similarity	NPC211093
0.7851	Intermediate Similarity	NPC473636
0.7845	Intermediate Similarity	NPC475922
0.7845	Intermediate Similarity	NPC218853
0.7845	Intermediate Similarity	NPC284828
0.7845	Intermediate Similarity	NPC173905
0.7845	Intermediate Similarity	NPC475065
0.7845	Intermediate Similarity	NPC472216
0.7845	Intermediate Similarity	NPC5475
0.784	Intermediate Similarity	NPC42399
0.784	Intermediate Similarity	NPC471940
0.784	Intermediate Similarity	NPC287423
0.7838	Intermediate Similarity	NPC278386
0.7838	Intermediate Similarity	NPC159763
0.7838	Intermediate Similarity	NPC124512

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 NPC475323 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	1716
0.2-0.3	3780
0.3-0.4	2322
0.4-0.5	681
0.5-0.6	286
0.6-0.7	146
0.7-0.8	11
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
0.8142	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8087	Intermediate Similarity	NPD6371	Approved
0.7838	Intermediate Similarity	NPD4225	Approved
0.7833	Intermediate Similarity	NPD7115	Discovery
0.7607	Intermediate Similarity	NPD6686	Approved
0.7578	Intermediate Similarity	NPD7319	Approved
0.7568	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD7507	Approved
0.7395	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7638	Approved
0.7304	Intermediate Similarity	NPD7640	Approved
0.7304	Intermediate Similarity	NPD7639	Approved
0.7287	Intermediate Similarity	NPD7078	Approved
0.7273	Intermediate Similarity	NPD1695	Approved
0.7266	Intermediate Similarity	NPD7492	Approved
0.7222	Intermediate Similarity	NPD6319	Approved
0.7222	Intermediate Similarity	NPD6054	Approved
0.7213	Intermediate Similarity	NPD6053	Discontinued
0.7209	Intermediate Similarity	NPD6616	Approved
0.7207	Intermediate Similarity	NPD46	Approved
0.7207	Intermediate Similarity	NPD6698	Approved
0.72	Intermediate Similarity	NPD7327	Approved
0.72	Intermediate Similarity	NPD7328	Approved
0.719	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD8033	Approved
0.7143	Intermediate Similarity	NPD7516	Approved
0.7109	Intermediate Similarity	NPD6370	Approved
0.7099	Intermediate Similarity	NPD7736	Approved
0.7094	Intermediate Similarity	NPD5344	Discontinued
0.7087	Intermediate Similarity	NPD8294	Approved
0.7087	Intermediate Similarity	NPD8377	Approved
0.7087	Intermediate Similarity	NPD6059	Approved
0.7031	Intermediate Similarity	NPD6016	Approved
0.7031	Intermediate Similarity	NPD8379	Approved
0.7031	Intermediate Similarity	NPD8296	Approved
0.7031	Intermediate Similarity	NPD8378	Approved
0.7031	Intermediate Similarity	NPD6015	Approved
0.7031	Intermediate Similarity	NPD8380	Approved
0.7031	Intermediate Similarity	NPD8335	Approved
0.7025	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD8293	Discontinued
0.7018	Intermediate Similarity	NPD5282	Discontinued
0.7016	Intermediate Similarity	NPD4632	Approved
0.7	Intermediate Similarity	NPD6008	Approved
0.6977	Remote Similarity	NPD5988	Approved
0.6942	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8297	Approved
0.693	Remote Similarity	NPD6399	Phase 3
0.6903	Remote Similarity	NPD5785	Approved
0.6885	Remote Similarity	NPD6899	Approved
0.6885	Remote Similarity	NPD7320	Approved
0.6885	Remote Similarity	NPD6881	Approved
0.686	Remote Similarity	NPD6675	Approved
0.686	Remote Similarity	NPD7128	Approved
0.686	Remote Similarity	NPD6402	Approved
0.686	Remote Similarity	NPD5739	Approved
0.6855	Remote Similarity	NPD6650	Approved
0.6855	Remote Similarity	NPD6649	Approved
0.6829	Remote Similarity	NPD6373	Approved
0.6829	Remote Similarity	NPD6372	Approved
0.6803	Remote Similarity	NPD6412	Phase 2
0.6803	Remote Similarity	NPD5697	Approved
0.6789	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7102	Approved
0.6774	Remote Similarity	NPD4634	Approved
0.6774	Remote Similarity	NPD6883	Approved
0.6774	Remote Similarity	NPD7290	Approved
0.6769	Remote Similarity	NPD8517	Approved
0.6769	Remote Similarity	NPD8515	Approved
0.6769	Remote Similarity	NPD8516	Approved
0.6769	Remote Similarity	NPD7503	Approved
0.6769	Remote Similarity	NPD8513	Phase 3
0.6754	Remote Similarity	NPD7838	Discovery
0.675	Remote Similarity	NPD7632	Discontinued
0.6723	Remote Similarity	NPD6648	Approved
0.672	Remote Similarity	NPD6847	Approved
0.672	Remote Similarity	NPD6617	Approved
0.672	Remote Similarity	NPD6869	Approved
0.672	Remote Similarity	NPD8130	Phase 1
0.6719	Remote Similarity	NPD6009	Approved
0.6696	Remote Similarity	NPD7637	Suspended
0.6696	Remote Similarity	NPD7983	Approved
0.6695	Remote Similarity	NPD6083	Phase 2
0.6695	Remote Similarity	NPD6084	Phase 2
0.6694	Remote Similarity	NPD6013	Approved
0.6694	Remote Similarity	NPD6014	Approved
0.6694	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.6641	Remote Similarity	NPD5983	Phase 2
0.6614	Remote Similarity	NPD8133	Approved
0.6613	Remote Similarity	NPD6011	Approved
0.6607	Remote Similarity	NPD1694	Approved
0.6593	Remote Similarity	NPD6033	Approved
0.6587	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6336	Discontinued
0.6555	Remote Similarity	NPD7902	Approved
0.6525	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5695	Phase 3
0.6519	Remote Similarity	NPD8074	Phase 3
0.65	Remote Similarity	NPD5696	Approved
0.65	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD5778	Approved
0.6496	Remote Similarity	NPD5779	Approved
0.6475	Remote Similarity	NPD5211	Phase 2
0.6462	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5363	Approved
0.6457	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7260	Phase 2
0.6446	Remote Similarity	NPD5286	Approved
0.6446	Remote Similarity	NPD4696	Approved
0.6446	Remote Similarity	NPD5285	Approved
0.6441	Remote Similarity	NPD7748	Approved
0.6429	Remote Similarity	NPD5362	Discontinued
0.6429	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4755	Approved
0.641	Remote Similarity	NPD8035	Phase 2
0.641	Remote Similarity	NPD7515	Phase 2
0.641	Remote Similarity	NPD6079	Approved
0.641	Remote Similarity	NPD8034	Phase 2
0.6404	Remote Similarity	NPD3618	Phase 1
0.6403	Remote Similarity	NPD6845	Suspended
0.6393	Remote Similarity	NPD1700	Approved
0.6391	Remote Similarity	NPD6921	Approved
0.6391	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6274	Approved
0.6379	Remote Similarity	NPD5328	Approved
0.6377	Remote Similarity	NPD5956	Approved
0.6372	Remote Similarity	NPD4786	Approved
0.6371	Remote Similarity	NPD5141	Approved
0.6364	Remote Similarity	NPD7101	Approved
0.6364	Remote Similarity	NPD7100	Approved
0.6356	Remote Similarity	NPD4202	Approved
0.6348	Remote Similarity	NPD7524	Approved
0.6348	Remote Similarity	NPD4250	Approved
0.6348	Remote Similarity	NPD4251	Approved
0.6341	Remote Similarity	NPD4633	Approved
0.6341	Remote Similarity	NPD5224	Approved
0.6341	Remote Similarity	NPD5225	Approved
0.6341	Remote Similarity	NPD5226	Approved
0.6316	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4700	Approved
0.6303	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7900	Approved
0.6296	Remote Similarity	NPD6067	Discontinued
0.6293	Remote Similarity	NPD6672	Approved
0.6293	Remote Similarity	NPD6903	Approved
0.6293	Remote Similarity	NPD5737	Approved
0.629	Remote Similarity	NPD5174	Approved
0.629	Remote Similarity	NPD5175	Approved
0.6288	Remote Similarity	NPD6335	Approved
0.6283	Remote Similarity	NPD7154	Phase 3
0.6271	Remote Similarity	NPD5281	Approved
0.6271	Remote Similarity	NPD5693	Phase 1
0.6271	Remote Similarity	NPD5284	Approved
0.6271	Remote Similarity	NPD6411	Approved
0.6261	Remote Similarity	NPD7146	Approved
0.6261	Remote Similarity	NPD7334	Approved
0.6261	Remote Similarity	NPD6684	Approved
0.6261	Remote Similarity	NPD5330	Approved
0.6261	Remote Similarity	NPD7521	Approved
0.6261	Remote Similarity	NPD6409	Approved
0.6261	Remote Similarity	NPD4249	Approved
0.6261	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5223	Approved
0.625	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD4629	Approved
0.625	Remote Similarity	NPD5210	Approved
0.6239	Remote Similarity	NPD4753	Phase 2
0.6228	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD6317	Approved
0.6198	Remote Similarity	NPD5221	Approved
0.6198	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD5222	Approved
0.6198	Remote Similarity	NPD4697	Phase 3
0.6195	Remote Similarity	NPD3667	Approved
0.6195	Remote Similarity	NPD4270	Approved
0.6195	Remote Similarity	NPD4269	Approved
0.6186	Remote Similarity	NPD5207	Approved
0.6174	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD6001	Approved
0.6165	Remote Similarity	NPD6313	Approved
0.6165	Remote Similarity	NPD6314	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5173	Approved
0.6148	Remote Similarity	NPD6908	Approved
0.6148	Remote Similarity	NPD6909	Approved
0.614	Remote Similarity	NPD6695	Phase 3
0.6136	Remote Similarity	NPD6868	Approved
0.6126	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5786	Approved
0.6119	Remote Similarity	NPD4522	Approved
0.6102	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6080	Approved
0.6102	Remote Similarity	NPD6051	Approved
0.6102	Remote Similarity	NPD6101	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data