NPASS Compound

Structure

NPC473656 OpenBabel07101718182D 37 42 0 0 1 0 0 0 0 0999 V2000 5.5656 1.4682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9986 -3.0792 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 5.9257 -0.2260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6167 -1.1771 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 0.0943 -2.4983 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 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 -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 0.7477 -2.4794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2566 0.5171 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 1 0 0 0 0 0 0 0 0 0 4.6385 -1.3850 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 0.8762 -1.8748 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 4.2784 0.3092 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 1.7422 -2.3748 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 0.3409 -3.3929 0.0000 O 0 0 0 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 3.6093 1.0523 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 3.9694 -0.6419 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 17 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 7 1 0 0 0 0 6 17 2 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 28 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 23 1 0 0 0 0 14 24 1 0 0 0 0 15 29 1 0 0 0 0 16 31 1 0 0 0 0 17 25 1 0 0 0 0 18 2 1 1 0 0 0 18 19 1 0 0 0 0 19 27 1 6 0 0 0 20 18 1 1 0 0 0 20 35 1 0 0 0 0 21 26 1 0 0 0 0 21 30 1 1 0 0 0 22 28 1 6 0 0 0 22 29 1 0 0 0 0 23 30 1 6 0 0 0 23 36 1 0 0 0 0 24 32 2 0 0 0 0 24 37 1 0 0 0 0 25 33 2 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 28 1 1 0 0 0 28 16 1 6 0 0 0 29 34 1 6 0 0 0 30 15 1 1 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.31
Volume:	529.719
LogP:	3.998
LogD:	3.395
LogS:	-4.566
# Rotatable Bonds:	3
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.545
Synthetic Accessibility Score:	6.08
Fsp3:	0.867
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:	-4.948
MDCK Permeability:	2.8571817892952822e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.364
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.341
Plasma Protein Binding (PPB):	79.24869537353516%
Volume Distribution (VD):	1.316
Pgp-substrate:	8.899935722351074%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.139
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.429
CYP2C9-inhibitor:	0.102
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.489

ADMET: Excretion

Clearance (CL):	8.749
Half-life (T1/2):	0.231

ADMET: Toxicity

hERG Blockers:	0.747
Human Hepatotoxicity (H-HT):	0.73
Drug-inuced Liver Injury (DILI):	0.218
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.665
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.945
Carcinogencity:	0.622
Eye Corrosion:	0.013
Eye Irritation:	0.021
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC473656

Natural Product ID:	NPC473656
*Common Name:**	Kadcoccilactone C
IUPAC Name:	n.a.
Synonyms:	Kadcoccilactone C
Standard InCHIKey:	HHTXECUEDFYGHX-NAQFNSOCSA-N
Standard InCHI:	InChI=1S/C30H44O7/c1-17-6-7-20(35-25(17)33)18(2)19-10-11-28(16-31)22-9-8-21-26(3,4)36-23-14-24(32)37-30(21,23)15-29(22,34)13-12-27(19,28)5/h6,18-23,31,34H,7-16H2,1-5H3/t18-,19-,20-,21-,22-,23+,27+,28+,29-,30+/m0/s1
SMILES:	CC1=CCC(OC1=O)C(C)C2CCC3(C2(CCC4(C3CCC5C(OC6C5(C4)OC(=O)C6)(C)C)O)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448238
PubChem CID:	24970812
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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	=	53.3	ug.mL-1	PMID[538253]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[538253]
NPT81	Cell Line	A549	Homo sapiens	IC	>	100.0	ug ml-1	PMID[538253]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[538253]

☑ 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 NPC473656 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	246
0.1-0.2	1375
0.2-0.3	4476
0.3-0.4	8219
0.4-0.5	13287
0.5-0.6	7340
0.6-0.7	6076
0.7-0.8	1651
0.8-0.85	19
0.85-0.9	3
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9725	High Similarity	NPC475372
0.9636	High Similarity	NPC312536
0.9279	High Similarity	NPC475323
0.9182	High Similarity	NPC473535
0.913	High Similarity	NPC129992
0.8644	High Similarity	NPC469352
0.8632	High Similarity	NPC67569
0.8571	High Similarity	NPC8369
0.8559	High Similarity	NPC23786
0.8559	High Similarity	NPC470265
0.8487	Intermediate Similarity	NPC469789
0.8455	Intermediate Similarity	NPC146731
0.8455	Intermediate Similarity	NPC296950
0.8455	Intermediate Similarity	NPC294259
0.8443	Intermediate Similarity	NPC475371
0.8443	Intermediate Similarity	NPC473593
0.8435	Intermediate Similarity	NPC123117
0.8421	Intermediate Similarity	NPC470063
0.8421	Intermediate Similarity	NPC269530
0.8407	Intermediate Similarity	NPC179642
0.8393	Intermediate Similarity	NPC255082
0.8376	Intermediate Similarity	NPC288679
0.8376	Intermediate Similarity	NPC50774
0.8376	Intermediate Similarity	NPC709
0.8364	Intermediate Similarity	NPC36688
0.8362	Intermediate Similarity	NPC470075
0.8347	Intermediate Similarity	NPC293112
0.8333	Intermediate Similarity	NPC11895
0.8333	Intermediate Similarity	NPC470076
0.8319	Intermediate Similarity	NPC46570
0.8305	Intermediate Similarity	NPC42673
0.8305	Intermediate Similarity	NPC475520
0.8305	Intermediate Similarity	NPC230513
0.8305	Intermediate Similarity	NPC469380
0.8304	Intermediate Similarity	NPC67321
0.8304	Intermediate Similarity	NPC187435
0.8291	Intermediate Similarity	NPC140055
0.8291	Intermediate Similarity	NPC469684
0.8291	Intermediate Similarity	NPC286528
0.8291	Intermediate Similarity	NPC20302
0.8291	Intermediate Similarity	NPC167606
0.8279	Intermediate Similarity	NPC42399
0.8276	Intermediate Similarity	NPC147912
0.8276	Intermediate Similarity	NPC474181
0.8276	Intermediate Similarity	NPC67259
0.8273	Intermediate Similarity	NPC476081
0.8273	Intermediate Similarity	NPC86077
0.8264	Intermediate Similarity	NPC8374
0.8261	Intermediate Similarity	NPC236217
0.8257	Intermediate Similarity	NPC47024
0.825	Intermediate Similarity	NPC269642
0.825	Intermediate Similarity	NPC107493
0.825	Intermediate Similarity	NPC287236
0.825	Intermediate Similarity	NPC170538
0.8246	Intermediate Similarity	NPC475134
0.8246	Intermediate Similarity	NPC235014
0.8246	Intermediate Similarity	NPC475563
0.8241	Intermediate Similarity	NPC73911
0.8235	Intermediate Similarity	NPC143755
0.8235	Intermediate Similarity	NPC474585
0.8235	Intermediate Similarity	NPC474370
0.822	Intermediate Similarity	NPC475913
0.8214	Intermediate Similarity	NPC472655
0.8211	Intermediate Similarity	NPC473620
0.8211	Intermediate Similarity	NPC470850
0.8205	Intermediate Similarity	NPC471127
0.8205	Intermediate Similarity	NPC138372
0.8205	Intermediate Similarity	NPC106228
0.8205	Intermediate Similarity	NPC154363
0.8205	Intermediate Similarity	NPC234858
0.8198	Intermediate Similarity	NPC168575
0.8198	Intermediate Similarity	NPC112009
0.8198	Intermediate Similarity	NPC159533
0.8198	Intermediate Similarity	NPC476237
0.8197	Intermediate Similarity	NPC473635
0.819	Intermediate Similarity	NPC470120
0.819	Intermediate Similarity	NPC312017
0.819	Intermediate Similarity	NPC477126
0.819	Intermediate Similarity	NPC122056
0.819	Intermediate Similarity	NPC9848
0.8174	Intermediate Similarity	NPC474846
0.8174	Intermediate Similarity	NPC469656
0.8174	Intermediate Similarity	NPC473921
0.8174	Intermediate Similarity	NPC475668
0.8174	Intermediate Similarity	NPC469655
0.8174	Intermediate Similarity	NPC475480
0.8165	Intermediate Similarity	NPC216478
0.816	Intermediate Similarity	NPC34963
0.8158	Intermediate Similarity	NPC42662
0.8158	Intermediate Similarity	NPC273433
0.8158	Intermediate Similarity	NPC472216
0.8158	Intermediate Similarity	NPC475065
0.8158	Intermediate Similarity	NPC284828
0.8158	Intermediate Similarity	NPC173905
0.8158	Intermediate Similarity	NPC5475
0.8151	Intermediate Similarity	NPC475834
0.8151	Intermediate Similarity	NPC472667
0.8151	Intermediate Similarity	NPC264954
0.8151	Intermediate Similarity	NPC474179
0.8151	Intermediate Similarity	NPC475041
0.8145	Intermediate Similarity	NPC35109
0.8145	Intermediate Similarity	NPC231529
0.8145	Intermediate Similarity	NPC476966
0.8142	Intermediate Similarity	NPC329048
0.8142	Intermediate Similarity	NPC330011
0.8142	Intermediate Similarity	NPC131665
0.8142	Intermediate Similarity	NPC255387
0.8136	Intermediate Similarity	NPC10721
0.8136	Intermediate Similarity	NPC98249
0.8136	Intermediate Similarity	NPC470492
0.8136	Intermediate Similarity	NPC470493
0.8136	Intermediate Similarity	NPC183580
0.8136	Intermediate Similarity	NPC58662
0.8136	Intermediate Similarity	NPC53396
0.8136	Intermediate Similarity	NPC284068
0.8136	Intermediate Similarity	NPC312824
0.8136	Intermediate Similarity	NPC476959
0.813	Intermediate Similarity	NPC287423
0.813	Intermediate Similarity	NPC298841
0.812	Intermediate Similarity	NPC238667
0.812	Intermediate Similarity	NPC216665
0.8115	Intermediate Similarity	NPC81736
0.8115	Intermediate Similarity	NPC172154
0.8108	Intermediate Similarity	NPC273005
0.8108	Intermediate Similarity	NPC31058
0.8108	Intermediate Similarity	NPC474709
0.8108	Intermediate Similarity	NPC469606
0.8103	Intermediate Similarity	NPC277769
0.8103	Intermediate Similarity	NPC23967
0.8103	Intermediate Similarity	NPC69291
0.8103	Intermediate Similarity	NPC4573
0.8099	Intermediate Similarity	NPC88326
0.8099	Intermediate Similarity	NPC153700
0.8095	Intermediate Similarity	NPC58029
0.8095	Intermediate Similarity	NPC469673
0.8091	Intermediate Similarity	NPC474012
0.8091	Intermediate Similarity	NPC476303
0.8091	Intermediate Similarity	NPC474718
0.8091	Intermediate Similarity	NPC476299
0.8087	Intermediate Similarity	NPC5103
0.8083	Intermediate Similarity	NPC154491
0.8083	Intermediate Similarity	NPC472004
0.8083	Intermediate Similarity	NPC476961
0.8083	Intermediate Similarity	NPC251226
0.8083	Intermediate Similarity	NPC268530
0.8083	Intermediate Similarity	NPC79579
0.8083	Intermediate Similarity	NPC4548
0.808	Intermediate Similarity	NPC196921
0.808	Intermediate Similarity	NPC241935
0.808	Intermediate Similarity	NPC220757
0.808	Intermediate Similarity	NPC279478
0.807	Intermediate Similarity	NPC151393
0.807	Intermediate Similarity	NPC475418
0.807	Intermediate Similarity	NPC189075
0.807	Intermediate Similarity	NPC275539
0.807	Intermediate Similarity	NPC94377
0.807	Intermediate Similarity	NPC473482
0.807	Intermediate Similarity	NPC318363
0.807	Intermediate Similarity	NPC306265
0.8067	Intermediate Similarity	NPC146280
0.8067	Intermediate Similarity	NPC284707
0.8067	Intermediate Similarity	NPC124676
0.8067	Intermediate Similarity	NPC186525
0.8067	Intermediate Similarity	NPC473720
0.8067	Intermediate Similarity	NPC153440
0.8053	Intermediate Similarity	NPC475217
0.8053	Intermediate Similarity	NPC475414
0.8053	Intermediate Similarity	NPC173172
0.8053	Intermediate Similarity	NPC469607
0.8051	Intermediate Similarity	NPC64318
0.8051	Intermediate Similarity	NPC72772
0.8051	Intermediate Similarity	NPC470793
0.8051	Intermediate Similarity	NPC190286
0.8051	Intermediate Similarity	NPC469794
0.8036	Intermediate Similarity	NPC180204
0.8036	Intermediate Similarity	NPC69171
0.8036	Intermediate Similarity	NPC474165
0.8036	Intermediate Similarity	NPC120321
0.8036	Intermediate Similarity	NPC474775
0.8036	Intermediate Similarity	NPC176883
0.8034	Intermediate Similarity	NPC472757
0.8034	Intermediate Similarity	NPC25909
0.8034	Intermediate Similarity	NPC469454
0.8034	Intermediate Similarity	NPC469463
0.8034	Intermediate Similarity	NPC469496
0.8033	Intermediate Similarity	NPC472399
0.8033	Intermediate Similarity	NPC469382
0.8031	Intermediate Similarity	NPC476823
0.8018	Intermediate Similarity	NPC308824
0.8018	Intermediate Similarity	NPC471412
0.8017	Intermediate Similarity	NPC4021
0.8017	Intermediate Similarity	NPC317107
0.8017	Intermediate Similarity	NPC474315
0.8017	Intermediate Similarity	NPC159456
0.8016	Intermediate Similarity	NPC231240
0.8	Intermediate Similarity	NPC473636
0.8	Intermediate Similarity	NPC5292
0.8	Intermediate Similarity	NPC124512
0.8	Intermediate Similarity	NPC476960
0.8	Intermediate Similarity	NPC159763

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 NPC473656 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	1722
0.2-0.3	3794
0.3-0.4	2304
0.4-0.5	660
0.5-0.6	255
0.6-0.7	172
0.7-0.8	24
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
0.8291	Intermediate Similarity	NPD7115	Discovery
0.8	Intermediate Similarity	NPD4225	Approved
0.7838	Intermediate Similarity	NPD7638	Approved
0.7826	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6371	Approved
0.7768	Intermediate Similarity	NPD7640	Approved
0.7768	Intermediate Similarity	NPD7639	Approved
0.7717	Intermediate Similarity	NPD7319	Approved
0.7698	Intermediate Similarity	NPD7078	Approved
0.768	Intermediate Similarity	NPD7492	Approved
0.7647	Intermediate Similarity	NPD6053	Discontinued
0.7642	Intermediate Similarity	NPD6054	Approved
0.7619	Intermediate Similarity	NPD7507	Approved
0.7619	Intermediate Similarity	NPD6616	Approved
0.752	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.7458	Intermediate Similarity	NPD6686	Approved
0.744	Intermediate Similarity	NPD6015	Approved
0.744	Intermediate Similarity	NPD6016	Approved
0.7436	Intermediate Similarity	NPD6008	Approved
0.7422	Intermediate Similarity	NPD8293	Discontinued
0.7411	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5988	Approved
0.7355	Intermediate Similarity	NPD8297	Approved
0.7339	Intermediate Similarity	NPD7328	Approved
0.7339	Intermediate Similarity	NPD7327	Approved
0.7333	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD7320	Approved
0.7311	Intermediate Similarity	NPD6899	Approved
0.7311	Intermediate Similarity	NPD6881	Approved
0.7302	Intermediate Similarity	NPD8033	Approved
0.7295	Intermediate Similarity	NPD4632	Approved
0.7288	Intermediate Similarity	NPD5739	Approved
0.7288	Intermediate Similarity	NPD6675	Approved
0.7288	Intermediate Similarity	NPD6402	Approved
0.7288	Intermediate Similarity	NPD7128	Approved
0.728	Intermediate Similarity	NPD7516	Approved
0.7273	Intermediate Similarity	NPD6650	Approved
0.7273	Intermediate Similarity	NPD6649	Approved
0.725	Intermediate Similarity	NPD6373	Approved
0.725	Intermediate Similarity	NPD6372	Approved
0.7232	Intermediate Similarity	NPD6399	Phase 3
0.7227	Intermediate Similarity	NPD5697	Approved
0.7222	Intermediate Similarity	NPD8377	Approved
0.7222	Intermediate Similarity	NPD8294	Approved
0.719	Intermediate Similarity	NPD6883	Approved
0.719	Intermediate Similarity	NPD7102	Approved
0.719	Intermediate Similarity	NPD7290	Approved
0.7179	Intermediate Similarity	NPD7632	Discontinued
0.7167	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD8296	Approved
0.7165	Intermediate Similarity	NPD8380	Approved
0.7165	Intermediate Similarity	NPD8335	Approved
0.7165	Intermediate Similarity	NPD7503	Approved
0.7165	Intermediate Similarity	NPD8378	Approved
0.7165	Intermediate Similarity	NPD8379	Approved
0.7131	Intermediate Similarity	NPD6869	Approved
0.7131	Intermediate Similarity	NPD6847	Approved
0.7131	Intermediate Similarity	NPD8130	Phase 1
0.7131	Intermediate Similarity	NPD6617	Approved
0.712	Intermediate Similarity	NPD6009	Approved
0.7117	Intermediate Similarity	NPD1695	Approved
0.7107	Intermediate Similarity	NPD6013	Approved
0.7107	Intermediate Similarity	NPD6012	Approved
0.7107	Intermediate Similarity	NPD6014	Approved
0.7094	Intermediate Similarity	NPD5344	Discontinued
0.7083	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5701	Approved
0.7073	Intermediate Similarity	NPD6882	Approved
0.7054	Intermediate Similarity	NPD46	Approved
0.7054	Intermediate Similarity	NPD5785	Approved
0.7054	Intermediate Similarity	NPD6698	Approved
0.7054	Intermediate Similarity	NPD7604	Phase 2
0.7049	Intermediate Similarity	NPD4634	Approved
0.7031	Intermediate Similarity	NPD8513	Phase 3
0.7031	Intermediate Similarity	NPD5983	Phase 2
0.7025	Intermediate Similarity	NPD6011	Approved
0.6991	Remote Similarity	NPD7637	Suspended
0.6983	Remote Similarity	NPD6084	Phase 2
0.6983	Remote Similarity	NPD6083	Phase 2
0.697	Remote Similarity	NPD6033	Approved
0.6957	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6336	Discontinued
0.6942	Remote Similarity	NPD6412	Phase 2
0.6909	Remote Similarity	NPD1694	Approved
0.6899	Remote Similarity	NPD8515	Approved
0.6899	Remote Similarity	NPD8517	Approved
0.6899	Remote Similarity	NPD8516	Approved
0.6891	Remote Similarity	NPD5211	Phase 2
0.688	Remote Similarity	NPD8133	Approved
0.687	Remote Similarity	NPD5282	Discontinued
0.6864	Remote Similarity	NPD5285	Approved
0.6864	Remote Similarity	NPD5286	Approved
0.6864	Remote Similarity	NPD6648	Approved
0.6864	Remote Similarity	NPD4696	Approved
0.6855	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD3618	Phase 1
0.6842	Remote Similarity	NPD8035	Phase 2
0.6842	Remote Similarity	NPD8034	Phase 2
0.6842	Remote Similarity	NPD6079	Approved
0.6838	Remote Similarity	NPD7902	Approved
0.6838	Remote Similarity	NPD4755	Approved
0.6814	Remote Similarity	NPD5328	Approved
0.681	Remote Similarity	NPD5695	Phase 3
0.6794	Remote Similarity	NPD8328	Phase 3
0.6789	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5779	Approved
0.6783	Remote Similarity	NPD5778	Approved
0.6783	Remote Similarity	NPD4202	Approved
0.678	Remote Similarity	NPD5696	Approved
0.6777	Remote Similarity	NPD5141	Approved
0.6772	Remote Similarity	NPD6274	Approved
0.6769	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5224	Approved
0.675	Remote Similarity	NPD5226	Approved
0.675	Remote Similarity	NPD4633	Approved
0.675	Remote Similarity	NPD5225	Approved
0.6744	Remote Similarity	NPD7101	Approved
0.6744	Remote Similarity	NPD7100	Approved
0.6724	Remote Similarity	NPD7748	Approved
0.6723	Remote Similarity	NPD4700	Approved
0.672	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7515	Phase 2
0.6696	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5174	Approved
0.6694	Remote Similarity	NPD5175	Approved
0.6691	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6642	Remote Similarity	NPD6845	Suspended
0.6642	Remote Similarity	NPD8074	Phase 3
0.6639	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5956	Approved
0.661	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5222	Approved
0.661	Remote Similarity	NPD4697	Phase 3
0.661	Remote Similarity	NPD5221	Approved
0.6609	Remote Similarity	NPD7838	Discovery
0.6607	Remote Similarity	NPD5363	Approved
0.6607	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD6317	Approved
0.6589	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6001	Approved
0.6581	Remote Similarity	NPD7900	Approved
0.6579	Remote Similarity	NPD6903	Approved
0.6579	Remote Similarity	NPD6672	Approved
0.6579	Remote Similarity	NPD5737	Approved
0.656	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5173	Approved
0.6552	Remote Similarity	NPD5693	Phase 1
0.6552	Remote Similarity	NPD5281	Approved
0.6552	Remote Similarity	NPD7983	Approved
0.6552	Remote Similarity	NPD5284	Approved
0.6552	Remote Similarity	NPD6411	Approved
0.6549	Remote Similarity	NPD7334	Approved
0.6549	Remote Similarity	NPD6409	Approved
0.6549	Remote Similarity	NPD7521	Approved
0.6549	Remote Similarity	NPD6684	Approved
0.6549	Remote Similarity	NPD5330	Approved
0.6549	Remote Similarity	NPD7146	Approved
0.6538	Remote Similarity	NPD6314	Approved
0.6538	Remote Similarity	NPD6313	Approved
0.6525	Remote Similarity	NPD4629	Approved
0.6525	Remote Similarity	NPD5210	Approved
0.6522	Remote Similarity	NPD4753	Phase 2
0.6518	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6908	Approved
0.6515	Remote Similarity	NPD6921	Approved
0.6515	Remote Similarity	NPD6909	Approved
0.6512	Remote Similarity	NPD6868	Approved
0.6491	Remote Similarity	NPD7524	Approved
0.6491	Remote Similarity	NPD4250	Approved
0.6491	Remote Similarity	NPD4251	Approved
0.6486	Remote Similarity	NPD3667	Approved
0.648	Remote Similarity	NPD4729	Approved
0.648	Remote Similarity	NPD5128	Approved
0.648	Remote Similarity	NPD4730	Approved
0.6466	Remote Similarity	NPD5207	Approved
0.646	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7525	Registered
0.6452	Remote Similarity	NPD4768	Approved
0.6452	Remote Similarity	NPD4767	Approved
0.6435	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5362	Discontinued
0.6429	Remote Similarity	NPD6695	Phase 3
0.6423	Remote Similarity	NPD4754	Approved
0.6404	Remote Similarity	NPD4249	Approved
0.6396	Remote Similarity	NPD5369	Approved
0.6379	Remote Similarity	NPD6080	Approved
0.6379	Remote Similarity	NPD6904	Approved
0.6379	Remote Similarity	NPD6101	Approved
0.6379	Remote Similarity	NPD5764	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