NPASS Compound

Structure

NPC312536 OpenBabel07101719512D 36 41 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 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 2 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 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 1.7422 2.3748 0.0000 C 0 0 2 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 0.7477 2.4794 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 16 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 16 2 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 29 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 22 1 0 0 0 0 14 23 1 0 0 0 0 15 27 1 0 0 0 0 16 24 1 0 0 0 0 17 2 1 6 0 0 0 17 18 1 0 0 0 0 18 26 1 1 0 0 0 19 17 1 6 0 0 0 19 34 1 0 0 0 0 20 25 1 0 0 0 0 20 28 1 6 0 0 0 21 27 1 1 0 0 0 21 29 1 0 0 0 0 22 28 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 2 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 29 1 6 0 0 0 27 32 1 1 0 0 0 28 15 1 6 0 0 0 28 36 1 0 0 0 0 29 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.29
Volume:	512.423
LogP:	3.945
LogD:	3.143
LogS:	-4.539
# Rotatable Bonds:	2
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.553
Synthetic Accessibility Score:	6.002
Fsp3:	0.862
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:	-5.064
MDCK Permeability:	2.3693826733506285e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.584
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.416
Plasma Protein Binding (PPB):	67.6055679321289%
Volume Distribution (VD):	0.943
Pgp-substrate:	12.121746063232422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.239
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.522
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.818
CYP3A4-substrate:	0.516

ADMET: Excretion

Clearance (CL):	9.901
Half-life (T1/2):	0.196

ADMET: Toxicity

hERG Blockers:	0.766
Human Hepatotoxicity (H-HT):	0.745
Drug-inuced Liver Injury (DILI):	0.256
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.295
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.895
Carcinogencity:	0.643
Eye Corrosion:	0.007
Eye Irritation:	0.015
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC312536

Natural Product ID:	NPC312536
*Common Name:**	Kadcoccilactone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UCYIJPSZTKEWLZ-CAQIMXKKSA-N
Standard InCHI:	InChI=1S/C29H42O7/c1-16-6-7-19(34-24(16)31)17(2)18-10-11-29(33)21-9-8-20-25(3,4)35-22-14-23(30)36-28(20,22)15-27(21,32)13-12-26(18,29)5/h6,17-22,32-33H,7-15H2,1-5H3/t17-,18-,19-,20-,21+,22+,26+,27-,28+,29-/m0/s1
SMILES:	O=C1C[C@@H]2[C@@]3(O1)C[C@@]1(O)CC[C@]4([C@]([C@@H]1CC[C@H]3C(O2)(C)C)(O)CC[C@H]4[C@@H]([C@@H]1CC=C(C(=O)O1)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450996
PubChem CID:	24970757
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[506867]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[506867]
NPT81	Cell Line	A549	Homo sapiens	IC	>	100.0	ug ml-1	PMID[506867]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[506867]

☑ 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 NPC312536 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	261
0.1-0.2	1481
0.2-0.3	4737
0.3-0.4	8248
0.4-0.5	13506
0.5-0.6	7622
0.6-0.7	5529
0.7-0.8	1285
0.8-0.85	20
0.85-0.9	3
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC475372
0.9636	High Similarity	NPC473656
0.9138	High Similarity	NPC129992
0.9018	High Similarity	NPC473535
0.8947	High Similarity	NPC475323
0.8655	High Similarity	NPC469352
0.8607	High Similarity	NPC475371
0.8559	High Similarity	NPC143755
0.8547	High Similarity	NPC288679
0.8475	Intermediate Similarity	NPC472667
0.8448	Intermediate Similarity	NPC123117
0.8421	Intermediate Similarity	NPC179642
0.8403	Intermediate Similarity	NPC4548
0.8403	Intermediate Similarity	NPC474585
0.8376	Intermediate Similarity	NPC470793
0.8374	Intermediate Similarity	NPC470850
0.8362	Intermediate Similarity	NPC470120
0.8333	Intermediate Similarity	NPC46570
0.8333	Intermediate Similarity	NPC67569
0.8319	Intermediate Similarity	NPC469380
0.8306	Intermediate Similarity	NPC231529
0.8304	Intermediate Similarity	NPC146731
0.8304	Intermediate Similarity	NPC294259
0.8293	Intermediate Similarity	NPC287423
0.8279	Intermediate Similarity	NPC8374
0.8279	Intermediate Similarity	NPC8369
0.8276	Intermediate Similarity	NPC269530
0.8264	Intermediate Similarity	NPC23786
0.8264	Intermediate Similarity	NPC269642
0.8264	Intermediate Similarity	NPC170538
0.8264	Intermediate Similarity	NPC107493
0.8264	Intermediate Similarity	NPC470265
0.825	Intermediate Similarity	NPC474370
0.825	Intermediate Similarity	NPC472004
0.8246	Intermediate Similarity	NPC255082
0.8235	Intermediate Similarity	NPC159928
0.8235	Intermediate Similarity	NPC153440
0.822	Intermediate Similarity	NPC190286
0.822	Intermediate Similarity	NPC106228
0.822	Intermediate Similarity	NPC469794
0.822	Intermediate Similarity	NPC72772
0.822	Intermediate Similarity	NPC138372
0.8211	Intermediate Similarity	NPC293112
0.8211	Intermediate Similarity	NPC473635
0.8205	Intermediate Similarity	NPC9848
0.8205	Intermediate Similarity	NPC477126
0.8205	Intermediate Similarity	NPC312017
0.8197	Intermediate Similarity	NPC469789
0.8197	Intermediate Similarity	NPC11895
0.8189	Intermediate Similarity	NPC476823
0.8182	Intermediate Similarity	NPC310511
0.8175	Intermediate Similarity	NPC34963
0.8167	Intermediate Similarity	NPC264954
0.8167	Intermediate Similarity	NPC230513
0.8167	Intermediate Similarity	NPC475520
0.8167	Intermediate Similarity	NPC475041
0.8167	Intermediate Similarity	NPC5292
0.816	Intermediate Similarity	NPC35109
0.816	Intermediate Similarity	NPC473593
0.816	Intermediate Similarity	NPC470851
0.8158	Intermediate Similarity	NPC67321
0.8158	Intermediate Similarity	NPC187435
0.8151	Intermediate Similarity	NPC469684
0.8142	Intermediate Similarity	NPC296950
0.8136	Intermediate Similarity	NPC43213
0.8136	Intermediate Similarity	NPC216665
0.8136	Intermediate Similarity	NPC90472
0.813	Intermediate Similarity	NPC81736
0.813	Intermediate Similarity	NPC172154
0.8125	Intermediate Similarity	NPC476081
0.812	Intermediate Similarity	NPC470063
0.812	Intermediate Similarity	NPC23967
0.8115	Intermediate Similarity	NPC88326
0.8115	Intermediate Similarity	NPC153700
0.811	Intermediate Similarity	NPC469673
0.811	Intermediate Similarity	NPC58029
0.8108	Intermediate Similarity	NPC47024
0.8103	Intermediate Similarity	NPC474923
0.8103	Intermediate Similarity	NPC48305
0.8099	Intermediate Similarity	NPC79579
0.8095	Intermediate Similarity	NPC196921
0.8095	Intermediate Similarity	NPC241935
0.8095	Intermediate Similarity	NPC220757
0.8095	Intermediate Similarity	NPC279478
0.8083	Intermediate Similarity	NPC709
0.8083	Intermediate Similarity	NPC50774
0.8067	Intermediate Similarity	NPC154363
0.8067	Intermediate Similarity	NPC471127
0.8067	Intermediate Similarity	NPC234858
0.8067	Intermediate Similarity	NPC470075
0.8053	Intermediate Similarity	NPC36688
0.8053	Intermediate Similarity	NPC168575
0.8053	Intermediate Similarity	NPC474775
0.8049	Intermediate Similarity	NPC471392
0.8049	Intermediate Similarity	NPC472399
0.8049	Intermediate Similarity	NPC473979
0.8049	Intermediate Similarity	NPC204812
0.8049	Intermediate Similarity	NPC469382
0.8034	Intermediate Similarity	NPC469655
0.8034	Intermediate Similarity	NPC474846
0.8034	Intermediate Similarity	NPC470076
0.8034	Intermediate Similarity	NPC469656
0.8031	Intermediate Similarity	NPC472769
0.8018	Intermediate Similarity	NPC216478
0.8017	Intermediate Similarity	NPC472216
0.8017	Intermediate Similarity	NPC42673
0.8017	Intermediate Similarity	NPC305260
0.8017	Intermediate Similarity	NPC42662
0.8017	Intermediate Similarity	NPC273433
0.8017	Intermediate Similarity	NPC270850
0.8017	Intermediate Similarity	NPC284828
0.8017	Intermediate Similarity	NPC173905
0.8017	Intermediate Similarity	NPC5475
0.8017	Intermediate Similarity	NPC9674
0.8017	Intermediate Similarity	NPC19028
0.8016	Intermediate Similarity	NPC472770
0.8	Intermediate Similarity	NPC117702
0.8	Intermediate Similarity	NPC26617
0.8	Intermediate Similarity	NPC470492
0.8	Intermediate Similarity	NPC286528
0.8	Intermediate Similarity	NPC36754
0.8	Intermediate Similarity	NPC53396
0.8	Intermediate Similarity	NPC20302
0.8	Intermediate Similarity	NPC471357
0.8	Intermediate Similarity	NPC140055
0.8	Intermediate Similarity	NPC98249
0.8	Intermediate Similarity	NPC42399
0.8	Intermediate Similarity	NPC10721
0.8	Intermediate Similarity	NPC146456
0.8	Intermediate Similarity	NPC475238
0.8	Intermediate Similarity	NPC58662
0.8	Intermediate Similarity	NPC469757
0.8	Intermediate Similarity	NPC167606
0.8	Intermediate Similarity	NPC302788
0.7984	Intermediate Similarity	NPC86346
0.7984	Intermediate Similarity	NPC241456
0.7984	Intermediate Similarity	NPC469379
0.7984	Intermediate Similarity	NPC32868
0.7984	Intermediate Similarity	NPC469790
0.7984	Intermediate Similarity	NPC75856
0.7983	Intermediate Similarity	NPC67259
0.7983	Intermediate Similarity	NPC147912
0.7983	Intermediate Similarity	NPC178289
0.7983	Intermediate Similarity	NPC471380
0.7983	Intermediate Similarity	NPC238667
0.7983	Intermediate Similarity	NPC474181
0.7982	Intermediate Similarity	NPC473577
0.7982	Intermediate Similarity	NPC475585
0.7982	Intermediate Similarity	NPC474550
0.7969	Intermediate Similarity	NPC88668
0.7967	Intermediate Similarity	NPC222688
0.7967	Intermediate Similarity	NPC287236
0.7966	Intermediate Similarity	NPC236217
0.7966	Intermediate Similarity	NPC191620
0.7965	Intermediate Similarity	NPC86077
0.7965	Intermediate Similarity	NPC22388
0.7953	Intermediate Similarity	NPC473838
0.7953	Intermediate Similarity	NPC475389
0.7951	Intermediate Similarity	NPC145074
0.7951	Intermediate Similarity	NPC157252
0.7951	Intermediate Similarity	NPC471126
0.7951	Intermediate Similarity	NPC114939
0.7951	Intermediate Similarity	NPC251226
0.7951	Intermediate Similarity	NPC145182
0.7951	Intermediate Similarity	NPC154491
0.7951	Intermediate Similarity	NPC471128
0.7951	Intermediate Similarity	NPC268530
0.7951	Intermediate Similarity	NPC41123
0.7949	Intermediate Similarity	NPC475134
0.7949	Intermediate Similarity	NPC475563
0.7949	Intermediate Similarity	NPC235014
0.7946	Intermediate Similarity	NPC476303
0.7937	Intermediate Similarity	NPC311534
0.7937	Intermediate Similarity	NPC473620
0.7937	Intermediate Similarity	NPC473888
0.7934	Intermediate Similarity	NPC186525
0.7934	Intermediate Similarity	NPC470420
0.7934	Intermediate Similarity	NPC475913
0.7934	Intermediate Similarity	NPC284707
0.7934	Intermediate Similarity	NPC161060
0.7934	Intermediate Similarity	NPC124676
0.7934	Intermediate Similarity	NPC146280
0.7934	Intermediate Similarity	NPC473720
0.7931	Intermediate Similarity	NPC475418
0.7931	Intermediate Similarity	NPC306265
0.7931	Intermediate Similarity	NPC318363
0.7931	Intermediate Similarity	NPC94377
0.7931	Intermediate Similarity	NPC473482
0.7928	Intermediate Similarity	NPC170143
0.7928	Intermediate Similarity	NPC108475
0.7928	Intermediate Similarity	NPC73911
0.7928	Intermediate Similarity	NPC213947
0.792	Intermediate Similarity	NPC15095
0.7917	Intermediate Similarity	NPC196931
0.7917	Intermediate Similarity	NPC270478
0.7917	Intermediate Similarity	NPC49492
0.7917	Intermediate Similarity	NPC64318
0.7917	Intermediate Similarity	NPC176840
0.7917	Intermediate Similarity	NPC266728
0.7913	Intermediate Similarity	NPC119855

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 NPC312536 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	1839
0.2-0.3	3854
0.3-0.4	2182
0.4-0.5	610
0.5-0.6	248
0.6-0.7	168
0.7-0.8	22
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
0.8	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7115	Discovery
0.7874	Intermediate Similarity	NPD7319	Approved
0.7797	Intermediate Similarity	NPD6371	Approved
0.7717	Intermediate Similarity	NPD7078	Approved
0.7699	Intermediate Similarity	NPD7638	Approved
0.7699	Intermediate Similarity	NPD4225	Approved
0.7698	Intermediate Similarity	NPD7492	Approved
0.7667	Intermediate Similarity	NPD6053	Discontinued
0.7661	Intermediate Similarity	NPD6054	Approved
0.7638	Intermediate Similarity	NPD6616	Approved
0.7638	Intermediate Similarity	NPD7507	Approved
0.7632	Intermediate Similarity	NPD7640	Approved
0.7632	Intermediate Similarity	NPD7639	Approved
0.7607	Intermediate Similarity	NPD6008	Approved
0.754	Intermediate Similarity	NPD6370	Approved
0.752	Intermediate Similarity	NPD6059	Approved
0.752	Intermediate Similarity	NPD6319	Approved
0.7519	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD7328	Approved
0.746	Intermediate Similarity	NPD6015	Approved
0.746	Intermediate Similarity	NPD6016	Approved
0.7442	Intermediate Similarity	NPD8293	Discontinued
0.744	Intermediate Similarity	NPD7516	Approved
0.7402	Intermediate Similarity	NPD5988	Approved
0.7377	Intermediate Similarity	NPD8297	Approved
0.7355	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6881	Approved
0.7333	Intermediate Similarity	NPD6899	Approved
0.7333	Intermediate Similarity	NPD7320	Approved
0.7323	Intermediate Similarity	NPD8033	Approved
0.7323	Intermediate Similarity	NPD8379	Approved
0.7323	Intermediate Similarity	NPD8296	Approved
0.7323	Intermediate Similarity	NPD8378	Approved
0.7323	Intermediate Similarity	NPD8380	Approved
0.7323	Intermediate Similarity	NPD8335	Approved
0.7317	Intermediate Similarity	NPD4632	Approved
0.7311	Intermediate Similarity	NPD6402	Approved
0.7311	Intermediate Similarity	NPD7128	Approved
0.7311	Intermediate Similarity	NPD5739	Approved
0.7311	Intermediate Similarity	NPD6675	Approved
0.7295	Intermediate Similarity	NPD6649	Approved
0.7295	Intermediate Similarity	NPD6650	Approved
0.7273	Intermediate Similarity	NPD6373	Approved
0.7273	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6372	Approved
0.725	Intermediate Similarity	NPD5697	Approved
0.7244	Intermediate Similarity	NPD8294	Approved
0.7244	Intermediate Similarity	NPD8377	Approved
0.7213	Intermediate Similarity	NPD7102	Approved
0.7213	Intermediate Similarity	NPD6883	Approved
0.7213	Intermediate Similarity	NPD7290	Approved
0.719	Intermediate Similarity	NPD6686	Approved
0.7188	Intermediate Similarity	NPD7503	Approved
0.7154	Intermediate Similarity	NPD8130	Phase 1
0.7154	Intermediate Similarity	NPD6617	Approved
0.7154	Intermediate Similarity	NPD6869	Approved
0.7154	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD1695	Approved
0.7131	Intermediate Similarity	NPD6014	Approved
0.7131	Intermediate Similarity	NPD6012	Approved
0.7131	Intermediate Similarity	NPD6013	Approved
0.713	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5701	Approved
0.7105	Intermediate Similarity	NPD6399	Phase 3
0.7097	Intermediate Similarity	NPD6882	Approved
0.708	Intermediate Similarity	NPD5785	Approved
0.7077	Intermediate Similarity	NPD7604	Phase 2
0.7073	Intermediate Similarity	NPD4634	Approved
0.7059	Intermediate Similarity	NPD7632	Discontinued
0.7054	Intermediate Similarity	NPD5983	Phase 2
0.7049	Intermediate Similarity	NPD6011	Approved
0.7049	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6084	Phase 2
0.7009	Intermediate Similarity	NPD6083	Phase 2
0.6992	Remote Similarity	NPD6033	Approved
0.6983	Remote Similarity	NPD5695	Phase 3
0.6975	Remote Similarity	NPD1700	Approved
0.6975	Remote Similarity	NPD5344	Discontinued
0.697	Remote Similarity	NPD6336	Discontinued
0.6967	Remote Similarity	NPD6412	Phase 2
0.6949	Remote Similarity	NPD5696	Approved
0.6917	Remote Similarity	NPD5211	Phase 2
0.6891	Remote Similarity	NPD5286	Approved
0.6891	Remote Similarity	NPD6648	Approved
0.6891	Remote Similarity	NPD5285	Approved
0.6891	Remote Similarity	NPD4696	Approved
0.688	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7637	Suspended
0.6864	Remote Similarity	NPD4755	Approved
0.681	Remote Similarity	NPD4202	Approved
0.6803	Remote Similarity	NPD5141	Approved
0.6797	Remote Similarity	NPD6274	Approved
0.6794	Remote Similarity	NPD8513	Phase 3
0.6794	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1694	Approved
0.6783	Remote Similarity	NPD46	Approved
0.6783	Remote Similarity	NPD6698	Approved
0.6777	Remote Similarity	NPD4633	Approved
0.6777	Remote Similarity	NPD5224	Approved
0.6777	Remote Similarity	NPD5226	Approved
0.6777	Remote Similarity	NPD5225	Approved
0.6772	Remote Similarity	NPD8133	Approved
0.6769	Remote Similarity	NPD7100	Approved
0.6769	Remote Similarity	NPD7101	Approved
0.6754	Remote Similarity	NPD6903	Approved
0.6752	Remote Similarity	NPD5282	Discontinued
0.6752	Remote Similarity	NPD6001	Approved
0.675	Remote Similarity	NPD4700	Approved
0.6726	Remote Similarity	NPD6684	Approved
0.6726	Remote Similarity	NPD7334	Approved
0.6726	Remote Similarity	NPD6409	Approved
0.6726	Remote Similarity	NPD7521	Approved
0.6726	Remote Similarity	NPD5330	Approved
0.6726	Remote Similarity	NPD7146	Approved
0.6726	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5284	Approved
0.6724	Remote Similarity	NPD5693	Phase 1
0.6724	Remote Similarity	NPD8034	Phase 2
0.6724	Remote Similarity	NPD5281	Approved
0.6724	Remote Similarity	NPD8035	Phase 2
0.6723	Remote Similarity	NPD7902	Approved
0.6721	Remote Similarity	NPD5174	Approved
0.6721	Remote Similarity	NPD5175	Approved
0.6694	Remote Similarity	NPD5223	Approved
0.6692	Remote Similarity	NPD6335	Approved
0.6692	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6642	Remote Similarity	NPD5956	Approved
0.6638	Remote Similarity	NPD5207	Approved
0.6637	Remote Similarity	NPD5363	Approved
0.6615	Remote Similarity	NPD6317	Approved
0.661	Remote Similarity	NPD7748	Approved
0.6609	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD7260	Phase 2
0.6581	Remote Similarity	NPD6079	Approved
0.6579	Remote Similarity	NPD3618	Phase 1
0.6567	Remote Similarity	NPD8328	Phase 3
0.6565	Remote Similarity	NPD6313	Approved
0.6565	Remote Similarity	NPD6314	Approved
0.6555	Remote Similarity	NPD5210	Approved
0.6555	Remote Similarity	NPD4629	Approved
0.6552	Remote Similarity	NPD4753	Phase 2
0.6552	Remote Similarity	NPD6904	Approved
0.6552	Remote Similarity	NPD6051	Approved
0.6552	Remote Similarity	NPD6673	Approved
0.6552	Remote Similarity	NPD5328	Approved
0.6552	Remote Similarity	NPD6080	Approved
0.6547	Remote Similarity	NPD6845	Suspended
0.6541	Remote Similarity	NPD6909	Approved
0.6541	Remote Similarity	NPD6908	Approved
0.6525	Remote Similarity	NPD5778	Approved
0.6525	Remote Similarity	NPD5779	Approved
0.6522	Remote Similarity	NPD4250	Approved
0.6522	Remote Similarity	NPD4251	Approved
0.6508	Remote Similarity	NPD4729	Approved
0.6508	Remote Similarity	NPD4730	Approved
0.6508	Remote Similarity	NPD5128	Approved
0.6491	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4767	Approved
0.648	Remote Similarity	NPD4768	Approved
0.6471	Remote Similarity	NPD7900	Approved
0.6471	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6672	Approved
0.6466	Remote Similarity	NPD5737	Approved
0.646	Remote Similarity	NPD5362	Discontinued
0.6452	Remote Similarity	NPD4754	Approved
0.6441	Remote Similarity	NPD7515	Phase 2
0.6441	Remote Similarity	NPD6050	Approved
0.6435	Remote Similarity	NPD4249	Approved
0.6429	Remote Similarity	NPD5369	Approved
0.6423	Remote Similarity	NPD8074	Phase 3
0.6418	Remote Similarity	NPD6921	Approved
0.6406	Remote Similarity	NPD5247	Approved
0.6406	Remote Similarity	NPD5248	Approved
0.6406	Remote Similarity	NPD5251	Approved
0.6406	Remote Similarity	NPD5250	Approved
0.6406	Remote Similarity	NPD5249	Phase 3
0.6404	Remote Similarity	NPD3665	Phase 1
0.6404	Remote Similarity	NPD3666	Approved
0.6404	Remote Similarity	NPD4786	Approved
0.6404	Remote Similarity	NPD3133	Approved
0.6404	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7524	Approved
0.6372	Remote Similarity	NPD4269	Approved
0.6372	Remote Similarity	NPD4223	Phase 3
0.6372	Remote Similarity	NPD4221	Approved
0.6372	Remote Similarity	NPD4270	Approved
0.6364	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5221	Approved
0.6364	Remote Similarity	NPD5222	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