NPASS Compound

Structure

NPC475371 OpenBabel07101718302D 38 45 0 0 1 0 0 0 0 0999 V2000 6.7038 2.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1649 -0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2912 1.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8545 2.3763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1160 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6789 1.1422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2558 4.5220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2818 2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3043 2.9197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7038 2.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7715 0.7218 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1649 1.8968 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.9159 2.1137 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0250 1.7872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8675 3.7310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3144 4.1847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1229 1.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1160 3.2058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8573 2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3308 2.1473 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3042 2.9047 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7565 -0.2781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9761 2.0962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5118 4.7480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4250 4.1569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3920 1.4562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1649 2.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8274 3.4505 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 -0.3443 3.1852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 13 1 0 0 0 0 6 19 1 0 0 0 0 7 14 1 0 0 0 0 7 16 1 0 0 0 0 8 18 1 0 0 0 0 8 20 1 0 0 0 0 9 17 1 0 0 0 0 9 25 1 0 0 0 0 10 25 1 0 0 0 0 11 23 1 0 0 0 0 12 2 1 1 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 27 1 1 0 0 0 14 22 1 0 0 0 0 14 29 1 6 0 0 0 15 21 1 0 0 0 0 15 34 1 0 0 0 0 16 24 1 0 0 0 0 16 26 1 1 0 0 0 17 27 1 6 0 0 0 17 30 1 0 0 0 0 18 26 1 6 0 0 0 18 35 1 0 0 0 0 19 28 1 1 0 0 0 19 36 1 0 0 0 0 20 31 2 0 0 0 0 20 37 1 0 0 0 0 21 38 1 6 0 0 0 22 25 1 6 0 0 0 22 28 1 0 0 0 0 23 32 2 0 0 0 0 23 34 1 0 0 0 0 24 35 1 0 0 0 0 25 33 1 6 0 0 0 26 10 1 1 0 0 0 26 37 1 0 0 0 0 27 28 1 1 0 0 0 27 38 1 0 0 0 0 28 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.23
Volume:	504.385
LogP:	2.71
LogD:	1.315
LogS:	-3.842
# Rotatable Bonds:	1
TPSA:	151.35
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	8
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.31
Synthetic Accessibility Score:	7.017
Fsp3:	0.821
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:	-5.78
MDCK Permeability:	4.0756247472018003e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.14
20% Bioavailability (F20%):	0.655
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148
Plasma Protein Binding (PPB):	62.844390869140625%
Volume Distribution (VD):	0.654
Pgp-substrate:	23.51396369934082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.692
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.292
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.236
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	8.632
Half-life (T1/2):	0.739

ADMET: Toxicity

hERG Blockers:	0.674
Human Hepatotoxicity (H-HT):	0.919
Drug-inuced Liver Injury (DILI):	0.726
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.415
Carcinogencity:	0.608
Eye Corrosion:	0.004
Eye Irritation:	0.009
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC475371

Natural Product ID:	NPC475371
*Common Name:**	Kadcoccilactone J
IUPAC Name:	n.a.
Synonyms:	Kadcoccilactone J
Standard InCHIKey:	QVDSQJYLZJYHMK-KILDTERBSA-N
Standard InCHI:	InChI=1S/C28H36O10/c1-11-5-15(34-23(11)32)21-12(2)13-6-19-28(36-19)22-14(29)7-16-24(3,4)35-18-8-20(31)37-26(16,18)10-25(22,33)9-17(30)27(13,28)38-21/h5,12-19,21-22,29-30,33H,6-10H2,1-4H3/t12-,13+,14+,15?,16-,17-,18+,19-,21-,22+,25-,26+,27+,28+/m0/s1
SMILES:	CC1C2CC3C4(C2(C(CC5(C4C(CC6C(OC7C6(C5)OC(=O)C7)(C)C)O)O)O)OC1C8C=C(C(=O)O8)C)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504449
PubChem CID:	44567837
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001818] Furopyrans

*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[493449]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[493449]
NPT81	Cell Line	A549	Homo sapiens	IC	>	100.0	ug ml-1	PMID[493449]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[493449]

☑ 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 NPC475371 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	323
0.1-0.2	1862
0.2-0.3	5816
0.3-0.4	10772
0.4-0.5	12787
0.5-0.6	7698
0.6-0.7	2982
0.7-0.8	442
0.8-0.85	10
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC469352
0.925	High Similarity	NPC129992
0.8607	High Similarity	NPC312536
0.8595	High Similarity	NPC475323
0.8525	High Similarity	NPC475372
0.8504	High Similarity	NPC470850
0.8443	Intermediate Similarity	NPC473656
0.8387	Intermediate Similarity	NPC143755
0.8387	Intermediate Similarity	NPC4548
0.8361	Intermediate Similarity	NPC470793
0.8333	Intermediate Similarity	NPC473802
0.8306	Intermediate Similarity	NPC472667
0.8295	Intermediate Similarity	NPC470851
0.8268	Intermediate Similarity	NPC473919
0.8268	Intermediate Similarity	NPC473709
0.8231	Intermediate Similarity	NPC475389
0.8231	Intermediate Similarity	NPC473838
0.822	Intermediate Similarity	NPC470980
0.8203	Intermediate Similarity	NPC471939
0.8168	Intermediate Similarity	NPC180902
0.8168	Intermediate Similarity	NPC475139
0.8162	Intermediate Similarity	NPC48414
0.8162	Intermediate Similarity	NPC5153
0.8154	Intermediate Similarity	NPC231529
0.8145	Intermediate Similarity	NPC475238
0.814	Intermediate Similarity	NPC471940
0.8095	Intermediate Similarity	NPC472004
0.8077	Intermediate Similarity	NPC476091
0.8077	Intermediate Similarity	NPC476078
0.8062	Intermediate Similarity	NPC217901
0.8045	Intermediate Similarity	NPC471137
0.8045	Intermediate Similarity	NPC473548
0.8045	Intermediate Similarity	NPC475500
0.8045	Intermediate Similarity	NPC223356
0.8045	Intermediate Similarity	NPC471136
0.8045	Intermediate Similarity	NPC475154
0.8045	Intermediate Similarity	NPC100017
0.8045	Intermediate Similarity	NPC182266
0.8015	Intermediate Similarity	NPC162495
0.8	Intermediate Similarity	NPC475273
0.8	Intermediate Similarity	NPC168849
0.7986	Intermediate Similarity	NPC48813
0.7986	Intermediate Similarity	NPC194854
0.7966	Intermediate Similarity	NPC470972
0.7955	Intermediate Similarity	NPC251564
0.7955	Intermediate Similarity	NPC475606
0.7955	Intermediate Similarity	NPC477189
0.7955	Intermediate Similarity	NPC475314
0.7937	Intermediate Similarity	NPC159928
0.7929	Intermediate Similarity	NPC16729
0.7929	Intermediate Similarity	NPC475462
0.7926	Intermediate Similarity	NPC68282
0.7917	Intermediate Similarity	NPC54737
0.7914	Intermediate Similarity	NPC471172
0.791	Intermediate Similarity	NPC471234
0.791	Intermediate Similarity	NPC476823
0.7907	Intermediate Similarity	NPC472399
0.7903	Intermediate Similarity	NPC477126
0.7895	Intermediate Similarity	NPC474508
0.7895	Intermediate Similarity	NPC473485
0.7895	Intermediate Similarity	NPC34963
0.7891	Intermediate Similarity	NPC310511
0.7879	Intermediate Similarity	NPC35109
0.7879	Intermediate Similarity	NPC104382
0.7879	Intermediate Similarity	NPC13071
0.7874	Intermediate Similarity	NPC469380
0.7869	Intermediate Similarity	NPC59489
0.7869	Intermediate Similarity	NPC139838
0.7868	Intermediate Similarity	NPC246209
0.7846	Intermediate Similarity	NPC144625
0.7842	Intermediate Similarity	NPC471171
0.7836	Intermediate Similarity	NPC58029
0.7836	Intermediate Similarity	NPC469673
0.7829	Intermediate Similarity	NPC23786
0.7829	Intermediate Similarity	NPC162009
0.7829	Intermediate Similarity	NPC470265
0.7829	Intermediate Similarity	NPC257017
0.782	Intermediate Similarity	NPC196921
0.782	Intermediate Similarity	NPC241935
0.782	Intermediate Similarity	NPC279478
0.782	Intermediate Similarity	NPC220757
0.7812	Intermediate Similarity	NPC471128
0.7812	Intermediate Similarity	NPC317635
0.7812	Intermediate Similarity	NPC142882
0.7812	Intermediate Similarity	NPC145182
0.7812	Intermediate Similarity	NPC329008
0.7812	Intermediate Similarity	NPC471126
0.7812	Intermediate Similarity	NPC157252
0.7803	Intermediate Similarity	NPC236999
0.7795	Intermediate Similarity	NPC161060
0.7795	Intermediate Similarity	NPC124676
0.7795	Intermediate Similarity	NPC146280
0.7787	Intermediate Similarity	NPC94377
0.7786	Intermediate Similarity	NPC293112
0.7786	Intermediate Similarity	NPC473635
0.7778	Intermediate Similarity	NPC471127
0.7778	Intermediate Similarity	NPC234858
0.7778	Intermediate Similarity	NPC106228
0.7778	Intermediate Similarity	NPC154363
0.7778	Intermediate Similarity	NPC138372
0.7769	Intermediate Similarity	NPC470979
0.7769	Intermediate Similarity	NPC473979
0.7769	Intermediate Similarity	NPC470975
0.7769	Intermediate Similarity	NPC103088
0.7769	Intermediate Similarity	NPC11895
0.7761	Intermediate Similarity	NPC472769
0.776	Intermediate Similarity	NPC473535
0.7752	Intermediate Similarity	NPC472401
0.7752	Intermediate Similarity	NPC52839
0.7752	Intermediate Similarity	NPC67569
0.7744	Intermediate Similarity	NPC175186
0.7744	Intermediate Similarity	NPC472770
0.7734	Intermediate Similarity	NPC9674
0.7734	Intermediate Similarity	NPC19028
0.7727	Intermediate Similarity	NPC287423
0.7717	Intermediate Similarity	NPC36754
0.7717	Intermediate Similarity	NPC10721
0.7717	Intermediate Similarity	NPC296822
0.771	Intermediate Similarity	NPC172154
0.771	Intermediate Similarity	NPC8369
0.771	Intermediate Similarity	NPC469790
0.771	Intermediate Similarity	NPC81736
0.771	Intermediate Similarity	NPC8374
0.7705	Intermediate Similarity	NPC26617
0.7704	Intermediate Similarity	NPC88668
0.7704	Intermediate Similarity	NPC224623
0.7698	Intermediate Similarity	NPC178289
0.7698	Intermediate Similarity	NPC123117
0.7698	Intermediate Similarity	NPC472400
0.7698	Intermediate Similarity	NPC216665
0.7698	Intermediate Similarity	NPC73314
0.7692	Intermediate Similarity	NPC19464
0.7692	Intermediate Similarity	NPC269642
0.7692	Intermediate Similarity	NPC222688
0.7692	Intermediate Similarity	NPC170538
0.7687	Intermediate Similarity	NPC471170
0.768	Intermediate Similarity	NPC23967
0.768	Intermediate Similarity	NPC471933
0.768	Intermediate Similarity	NPC473877
0.7674	Intermediate Similarity	NPC475885
0.7674	Intermediate Similarity	NPC251226
0.7674	Intermediate Similarity	NPC474370
0.7667	Intermediate Similarity	NPC86077
0.7661	Intermediate Similarity	NPC48305
0.7661	Intermediate Similarity	NPC179642
0.7661	Intermediate Similarity	NPC474923
0.7656	Intermediate Similarity	NPC470420
0.7656	Intermediate Similarity	NPC472397
0.7656	Intermediate Similarity	NPC171905
0.7656	Intermediate Similarity	NPC288679
0.7656	Intermediate Similarity	NPC472758
0.7656	Intermediate Similarity	NPC471125
0.7652	Intermediate Similarity	NPC15095
0.7652	Intermediate Similarity	NPC470973
0.7638	Intermediate Similarity	NPC474333
0.7634	Intermediate Similarity	NPC469789
0.7634	Intermediate Similarity	NPC471392
0.7634	Intermediate Similarity	NPC469382
0.7627	Intermediate Similarity	NPC472998
0.7623	Intermediate Similarity	NPC223450
0.7623	Intermediate Similarity	NPC243998
0.7623	Intermediate Similarity	NPC475290
0.7619	Intermediate Similarity	NPC470120
0.7619	Intermediate Similarity	NPC472757
0.7615	Intermediate Similarity	NPC159456
0.7615	Intermediate Similarity	NPC4021
0.7612	Intermediate Similarity	NPC470880
0.7612	Intermediate Similarity	NPC473593
0.7597	Intermediate Similarity	NPC5991
0.7597	Intermediate Similarity	NPC264954
0.7597	Intermediate Similarity	NPC5989
0.7597	Intermediate Similarity	NPC236918
0.7597	Intermediate Similarity	NPC156745
0.7597	Intermediate Similarity	NPC471108
0.7597	Intermediate Similarity	NPC42673
0.7597	Intermediate Similarity	NPC22628
0.7597	Intermediate Similarity	NPC255081
0.7597	Intermediate Similarity	NPC470186
0.7597	Intermediate Similarity	NPC275696
0.7594	Intermediate Similarity	NPC117702
0.7594	Intermediate Similarity	NPC42399
0.7594	Intermediate Similarity	NPC469757
0.7594	Intermediate Similarity	NPC471357
0.7594	Intermediate Similarity	NPC146456
0.7583	Intermediate Similarity	NPC150923
0.7581	Intermediate Similarity	NPC471934
0.7581	Intermediate Similarity	NPC42662
0.7578	Intermediate Similarity	NPC58662
0.7578	Intermediate Similarity	NPC98249
0.7578	Intermediate Similarity	NPC53396
0.7578	Intermediate Similarity	NPC156252
0.7578	Intermediate Similarity	NPC469684
0.7576	Intermediate Similarity	NPC469379
0.7576	Intermediate Similarity	NPC145238
0.7576	Intermediate Similarity	NPC75856
0.7576	Intermediate Similarity	NPC86346
0.7574	Intermediate Similarity	NPC470427
0.7574	Intermediate Similarity	NPC327664
0.7574	Intermediate Similarity	NPC476097
0.7574	Intermediate Similarity	NPC24599

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 NPC475371 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	2306
0.2-0.3	3997
0.3-0.4	1777
0.4-0.5	499
0.5-0.6	229
0.6-0.7	59
0.7-0.8	0
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
0.7705	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD7319	Approved
0.7442	Intermediate Similarity	NPD7115	Discovery
0.7381	Intermediate Similarity	NPD6371	Approved
0.7328	Intermediate Similarity	NPD7516	Approved
0.7302	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD5344	Discontinued
0.7259	Intermediate Similarity	NPD7507	Approved
0.7252	Intermediate Similarity	NPD7327	Approved
0.7252	Intermediate Similarity	NPD7328	Approved
0.7244	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6319	Approved
0.7132	Intermediate Similarity	NPD6053	Discontinued
0.709	Intermediate Similarity	NPD8033	Approved
0.708	Intermediate Similarity	NPD7078	Approved
0.7059	Intermediate Similarity	NPD7492	Approved
0.7015	Intermediate Similarity	NPD6054	Approved
0.7008	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6616	Approved
0.6992	Remote Similarity	NPD4225	Approved
0.6975	Remote Similarity	NPD6698	Approved
0.6975	Remote Similarity	NPD46	Approved
0.6963	Remote Similarity	NPD8380	Approved
0.6963	Remote Similarity	NPD8379	Approved
0.6963	Remote Similarity	NPD8296	Approved
0.6963	Remote Similarity	NPD8378	Approved
0.6963	Remote Similarity	NPD8335	Approved
0.6935	Remote Similarity	NPD6648	Approved
0.6929	Remote Similarity	NPD6008	Approved
0.6912	Remote Similarity	NPD6370	Approved
0.6906	Remote Similarity	NPD7736	Approved
0.6891	Remote Similarity	NPD1695	Approved
0.6889	Remote Similarity	NPD8377	Approved
0.6889	Remote Similarity	NPD6059	Approved
0.6889	Remote Similarity	NPD8294	Approved
0.688	Remote Similarity	NPD1700	Approved
0.6855	Remote Similarity	NPD7638	Approved
0.6838	Remote Similarity	NPD6015	Approved
0.6838	Remote Similarity	NPD6016	Approved
0.6835	Remote Similarity	NPD8293	Discontinued
0.6822	Remote Similarity	NPD6686	Approved
0.68	Remote Similarity	NPD7640	Approved
0.68	Remote Similarity	NPD7639	Approved
0.6788	Remote Similarity	NPD5988	Approved
0.6742	Remote Similarity	NPD8297	Approved
0.6692	Remote Similarity	NPD4632	Approved
0.6692	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6641	Remote Similarity	NPD6373	Approved
0.6641	Remote Similarity	NPD6372	Approved
0.6594	Remote Similarity	NPD7503	Approved
0.6591	Remote Similarity	NPD4634	Approved
0.6565	Remote Similarity	NPD7320	Approved
0.6565	Remote Similarity	NPD6899	Approved
0.6565	Remote Similarity	NPD6881	Approved
0.6557	Remote Similarity	NPD7838	Discovery
0.6538	Remote Similarity	NPD6402	Approved
0.6538	Remote Similarity	NPD5739	Approved
0.6538	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD6675	Approved
0.65	Remote Similarity	NPD7604	Phase 2
0.6493	Remote Similarity	NPD6882	Approved
0.6489	Remote Similarity	NPD5697	Approved
0.648	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8513	Phase 3
0.6475	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD8517	Approved
0.6475	Remote Similarity	NPD8515	Approved
0.6466	Remote Similarity	NPD7102	Approved
0.6466	Remote Similarity	NPD6883	Approved
0.6466	Remote Similarity	NPD7290	Approved
0.6434	Remote Similarity	NPD6033	Approved
0.6423	Remote Similarity	NPD5785	Approved
0.6423	Remote Similarity	NPD6009	Approved
0.6418	Remote Similarity	NPD6617	Approved
0.6418	Remote Similarity	NPD6847	Approved
0.6418	Remote Similarity	NPD6869	Approved
0.6418	Remote Similarity	NPD8130	Phase 1
0.6391	Remote Similarity	NPD6012	Approved
0.6391	Remote Similarity	NPD6014	Approved
0.6391	Remote Similarity	NPD6013	Approved
0.6364	Remote Similarity	NPD6412	Phase 2
0.6364	Remote Similarity	NPD5701	Approved
0.6357	Remote Similarity	NPD5983	Phase 2
0.6349	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD8133	Approved
0.6316	Remote Similarity	NPD6011	Approved
0.6311	Remote Similarity	NPD4250	Approved
0.6311	Remote Similarity	NPD4251	Approved
0.6308	Remote Similarity	NPD7632	Discontinued
0.6294	Remote Similarity	NPD6336	Discontinued
0.6281	Remote Similarity	NPD5363	Approved
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD8074	Phase 3
0.625	Remote Similarity	NPD6084	Phase 2
0.6241	Remote Similarity	NPD6921	Approved
0.624	Remote Similarity	NPD7983	Approved
0.623	Remote Similarity	NPD4249	Approved
0.619	Remote Similarity	NPD6399	Phase 3
0.6183	Remote Similarity	NPD5211	Phase 2
0.6176	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8328	Phase 3
0.6154	Remote Similarity	NPD5285	Approved
0.6154	Remote Similarity	NPD4696	Approved
0.6154	Remote Similarity	NPD6067	Discontinued
0.6154	Remote Similarity	NPD5286	Approved
0.6148	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD4755	Approved
0.6122	Remote Similarity	NPD5956	Approved
0.6116	Remote Similarity	NPD5362	Discontinued
0.6115	Remote Similarity	NPD6274	Approved
0.6111	Remote Similarity	NPD7637	Suspended
0.6099	Remote Similarity	NPD7101	Approved
0.6099	Remote Similarity	NPD7100	Approved
0.6094	Remote Similarity	NPD5695	Phase 3
0.609	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.609	Remote Similarity	NPD5141	Approved
0.609	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD5369	Approved
0.6077	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD5696	Approved
0.6063	Remote Similarity	NPD4202	Approved
0.6063	Remote Similarity	NPD5778	Approved
0.6063	Remote Similarity	NPD5779	Approved
0.6061	Remote Similarity	NPD4633	Approved
0.6061	Remote Similarity	NPD5224	Approved
0.6061	Remote Similarity	NPD5225	Approved
0.6061	Remote Similarity	NPD5226	Approved
0.6033	Remote Similarity	NPD4270	Approved
0.6033	Remote Similarity	NPD4269	Approved
0.6031	Remote Similarity	NPD4700	Approved
0.6029	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD6335	Approved
0.6016	Remote Similarity	NPD5282	Discontinued
0.6016	Remote Similarity	NPD6001	Approved
0.6015	Remote Similarity	NPD5174	Approved
0.6015	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD4821	Approved
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4822	Approved
0.6	Remote Similarity	NPD4819	Approved
0.6	Remote Similarity	NPD4820	Approved
0.5985	Remote Similarity	NPD5223	Approved
0.5973	Remote Similarity	NPD7260	Phase 2
0.5968	Remote Similarity	NPD5786	Approved
0.5959	Remote Similarity	NPD8273	Phase 1
0.5957	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6317	Approved
0.5956	Remote Similarity	NPD4730	Approved
0.5956	Remote Similarity	NPD4729	Approved
0.5949	Remote Similarity	NPD7625	Phase 1
0.5933	Remote Similarity	NPD8338	Approved
0.5933	Remote Similarity	NPD6845	Suspended
0.5931	Remote Similarity	NPD7642	Approved
0.5926	Remote Similarity	NPD4768	Approved
0.5926	Remote Similarity	NPD4767	Approved
0.592	Remote Similarity	NPD7524	Approved
0.5915	Remote Similarity	NPD6314	Approved
0.5915	Remote Similarity	NPD6313	Approved
0.5903	Remote Similarity	NPD6909	Approved
0.5903	Remote Similarity	NPD6908	Approved
0.5902	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6435	Approved
0.5896	Remote Similarity	NPD7799	Discontinued
0.5887	Remote Similarity	NPD1694	Approved
0.5882	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD7902	Approved
0.5874	Remote Similarity	NPD4522	Approved
0.5873	Remote Similarity	NPD6903	Approved
0.587	Remote Similarity	NPD5250	Approved
0.587	Remote Similarity	NPD5251	Approved
0.587	Remote Similarity	NPD5247	Approved
0.587	Remote Similarity	NPD5248	Approved
0.587	Remote Similarity	NPD5249	Phase 3
0.5868	Remote Similarity	NPD4252	Approved
0.5865	Remote Similarity	NPD4159	Approved
0.5859	Remote Similarity	NPD6079	Approved
0.5859	Remote Similarity	NPD5284	Approved
0.5859	Remote Similarity	NPD5281	Approved
0.5859	Remote Similarity	NPD5693	Phase 1
0.5859	Remote Similarity	NPD8034	Phase 2
0.5859	Remote Similarity	NPD8035	Phase 2
0.5854	Remote Similarity	NPD7154	Phase 3
0.5846	Remote Similarity	NPD4629	Approved
0.5846	Remote Similarity	NPD5210	Approved
0.5844	Remote Similarity	NPD6333	Approved
0.5844	Remote Similarity	NPD6334	Approved
0.584	Remote Similarity	NPD3618	Phase 1
0.584	Remote Similarity	NPD7334	Approved
0.584	Remote Similarity	NPD6684	Approved
0.584	Remote Similarity	NPD5330	Approved
0.584	Remote Similarity	NPD7146	Approved
0.584	Remote Similarity	NPD6409	Approved
0.584	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.584	Remote Similarity	NPD7521	Approved
0.5839	Remote Similarity	NPD5128	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