NPASS Compound

Structure

NPC60150 OpenBabel07101719142D 54 63 0 0 1 0 0 0 0 0999 V2000 7.5776 -3.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1993 -0.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7113 -3.8925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6135 -1.4623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2882 -2.0764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7619 0.0836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0767 0.2741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9708 -2.2791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9873 -1.5681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2926 -5.6487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7763 -3.7048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5396 -2.3157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9866 -3.7897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1747 -0.5082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9771 -4.0310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7244 -2.9463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2171 -0.4361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8219 -1.1258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6886 -1.8244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8929 -4.7509 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3766 -2.8071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7990 -3.6021 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8702 -4.8537 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5396 -3.2984 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8376 -3.2984 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3482 -0.3190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3667 0.2318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7283 -1.0682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9866 -1.8244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1355 -2.3157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2747 -3.4973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7670 0.2241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0911 -1.8495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7036 -1.2187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6886 -3.7897 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7990 -2.0121 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1355 -3.2984 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2699 -3.9559 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8376 -2.3157 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0239 -0.7987 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0303 0.3884 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1476 1.1897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9234 -4.2355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0985 1.1492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0600 -2.0133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5318 -0.6897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5352 -4.1961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0576 -3.3684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3251 -2.2716 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7720 -0.8902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7090 -0.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6705 -3.8724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5989 -2.4444 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 2 17 1 0 0 0 0 5 49 1 0 0 0 0 6 7 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 9 1 0 0 0 0 8 16 2 0 0 0 0 9 50 1 0 0 0 0 10 20 1 0 0 0 0 10 23 1 0 0 0 0 11 21 1 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 13 37 1 0 0 0 0 14 18 1 0 0 0 0 14 51 1 0 0 0 0 15 38 1 0 0 0 0 15 52 1 0 0 0 0 16 31 1 0 0 0 0 17 28 2 0 0 0 0 17 32 1 0 0 0 0 18 19 2 0 0 0 0 18 33 1 0 0 0 0 20 23 1 0 0 0 0 20 35 1 1 0 0 0 21 22 1 0 0 0 0 21 36 1 1 0 0 0 22 37 1 1 0 0 0 23 38 1 1 0 0 0 24 35 1 1 0 0 0 24 38 1 0 0 0 0 25 35 1 6 0 0 0 25 39 1 0 0 0 0 26 41 2 0 0 0 0 26 50 1 0 0 0 0 27 42 2 0 0 0 0 27 51 1 0 0 0 0 28 29 1 0 0 0 0 28 40 1 0 0 0 0 29 30 2 0 0 0 0 29 39 1 0 0 0 0 30 36 1 0 0 0 0 30 37 1 0 0 0 0 31 43 2 0 0 0 0 31 52 1 0 0 0 0 32 44 2 0 0 0 0 32 54 1 0 0 0 0 33 45 2 0 0 0 0 33 53 1 0 0 0 0 34 36 1 1 0 0 0 34 40 1 0 0 0 0 34 46 1 0 0 0 0 35 3 1 1 0 0 0 36 4 1 1 0 0 0 37 47 1 1 0 0 0 38 48 1 1 0 0 0 39 19 1 6 0 0 0 39 53 1 0 0 0 0 40 49 1 1 0 0 0 40 54 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	339.15
Volume:	347.953
LogP:	3.469
LogD:	2.917
LogS:	-3.677
# Rotatable Bonds:	2
TPSA:	62.16
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.701
Synthetic Accessibility Score:	2.668
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.989
MDCK Permeability:	1.4935609215172008e-05
Pgp-inhibitor:	0.06
Pgp-substrate:	0.379
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.805
Plasma Protein Binding (PPB):	88.72608184814453%
Volume Distribution (VD):	1.348
Pgp-substrate:	12.648344039916992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.909
CYP1A2-substrate:	0.981
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.7
CYP2D6-inhibitor:	0.361
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.818

ADMET: Excretion

Clearance (CL):	14.197
Half-life (T1/2):	0.604

ADMET: Toxicity

hERG Blockers:	0.758
Human Hepatotoxicity (H-HT):	0.541
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.687
Rat Oral Acute Toxicity:	0.841
Maximum Recommended Daily Dose:	0.72
Skin Sensitization:	0.925
Carcinogencity:	0.171
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC60150

Natural Product ID:	NPC60150
*Common Name:**	NASSYBOEZYWDCR-FWRLJKOGSA-N
IUPAC Name:	n.a.
Synonyms:	8-O-Methyltianmushanol
Standard InCHIKey:	NASSYBOEZYWDCR-FWRLJKOGSA-N
Standard InCHI:	InChI=1S/C40H44O14/c1-16-8-9-50-26(41)6-7-27(42)51-14-18-19-12-24-35(3,20-10-23(20)38(24,48)15-52-31(16)43)25-13-37(47)22-11-21(22)36(4)30(37)29(39(19,25)53-33(18)45)28-17(2)32(44)54-40(28,49-5)34(36)46/h8,20-25,34,46-48H,6-7,9-15H2,1-5H3/b16-8+/t20-,21-,22+,23+,24-,25+,34-,35+,36+,37+,38+,39+,40-/m1/s1
SMILES:	C/C/1=CCOC(=O)CCC(=O)OCC2=C3C[C@@H]4[C@](C)([C@@H]5C[C@@H]5[C@]4(COC1=O)O)[C@@H]1C[C@@]4([C@H]5C[C@H]5[C@@]5(C)C4=C(C4=C(C)C(=O)O[C@]4([C@@H]5O)OC)[C@]31OC2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505283
PubChem CID:	24878684
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO24744	Chloranthus tianmushanensis	Species	Chloranthaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18357995]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053511]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22372956]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588583]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724564]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24744	Chloranthus tianmushanensis	Species	Chloranthaceae	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	1
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	312000.0	nM	PMID[523245]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	<	50.0	%	PMID[523246]

☑ 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 NPC60150 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	303
0.1-0.2	1660
0.2-0.3	5064
0.3-0.4	9706
0.4-0.5	12923
0.5-0.6	7958
0.6-0.7	4342
0.7-0.8	683
0.8-0.85	30
0.85-0.9	7
0.9-0.95	9
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC192334
0.9918	High Similarity	NPC327664
0.9918	High Similarity	NPC470427
0.9918	High Similarity	NPC24599
0.9918	High Similarity	NPC476097
0.9836	High Similarity	NPC476824
0.9754	High Similarity	NPC254823
0.9672	High Similarity	NPC134902
0.9344	High Similarity	NPC226049
0.9262	High Similarity	NPC84865
0.918	High Similarity	NPC27335
0.916	High Similarity	NPC470426
0.9084	High Similarity	NPC25887
0.9008	High Similarity	NPC476825
0.8692	High Similarity	NPC469674
0.8692	High Similarity	NPC469673
0.8626	High Similarity	NPC476823
0.8615	High Similarity	NPC34963
0.855	High Similarity	NPC58029
0.8538	High Similarity	NPC220757
0.8538	High Similarity	NPC279478
0.8538	High Similarity	NPC241935
0.8538	High Similarity	NPC196921
0.8462	Intermediate Similarity	NPC35109
0.8231	Intermediate Similarity	NPC15095
0.8092	Intermediate Similarity	NPC63186
0.8031	Intermediate Similarity	NPC203862
0.797	Intermediate Similarity	NPC311534
0.7953	Intermediate Similarity	NPC470075
0.7939	Intermediate Similarity	NPC129992
0.7926	Intermediate Similarity	NPC231240
0.791	Intermediate Similarity	NPC473593
0.7907	Intermediate Similarity	NPC29639
0.7907	Intermediate Similarity	NPC44899
0.7907	Intermediate Similarity	NPC304260
0.7907	Intermediate Similarity	NPC5883
0.7895	Intermediate Similarity	NPC287423
0.7895	Intermediate Similarity	NPC42399
0.7891	Intermediate Similarity	NPC93883
0.7879	Intermediate Similarity	NPC8374
0.7874	Intermediate Similarity	NPC106446
0.7868	Intermediate Similarity	NPC316915
0.7863	Intermediate Similarity	NPC470265
0.7863	Intermediate Similarity	NPC115349
0.7863	Intermediate Similarity	NPC23786
0.7846	Intermediate Similarity	NPC17938
0.7846	Intermediate Similarity	NPC107607
0.7836	Intermediate Similarity	NPC473888
0.7829	Intermediate Similarity	NPC218093
0.7817	Intermediate Similarity	NPC471172
0.7812	Intermediate Similarity	NPC99620
0.7812	Intermediate Similarity	NPC193382
0.7812	Intermediate Similarity	NPC5311
0.7812	Intermediate Similarity	NPC199428
0.7812	Intermediate Similarity	NPC310341
0.7801	Intermediate Similarity	NPC5153
0.7801	Intermediate Similarity	NPC48414
0.7795	Intermediate Similarity	NPC264153
0.7787	Intermediate Similarity	NPC85742
0.7786	Intermediate Similarity	NPC67569
0.7786	Intermediate Similarity	NPC46570
0.7786	Intermediate Similarity	NPC231518
0.7786	Intermediate Similarity	NPC475219
0.7786	Intermediate Similarity	NPC40749
0.7778	Intermediate Similarity	NPC476966
0.7778	Intermediate Similarity	NPC231529
0.7778	Intermediate Similarity	NPC471407
0.7769	Intermediate Similarity	NPC268326
0.7769	Intermediate Similarity	NPC32177
0.7769	Intermediate Similarity	NPC470897
0.7769	Intermediate Similarity	NPC153085
0.7769	Intermediate Similarity	NPC81222
0.7769	Intermediate Similarity	NPC55532
0.7769	Intermediate Similarity	NPC292467
0.7769	Intermediate Similarity	NPC30483
0.7769	Intermediate Similarity	NPC236973
0.7769	Intermediate Similarity	NPC469756
0.7769	Intermediate Similarity	NPC291820
0.7761	Intermediate Similarity	NPC117702
0.7761	Intermediate Similarity	NPC469757
0.7761	Intermediate Similarity	NPC471357
0.7761	Intermediate Similarity	NPC146456
0.7752	Intermediate Similarity	NPC87250
0.7752	Intermediate Similarity	NPC471353
0.7752	Intermediate Similarity	NPC84987
0.7752	Intermediate Similarity	NPC27507
0.7752	Intermediate Similarity	NPC158344
0.7752	Intermediate Similarity	NPC244402
0.7752	Intermediate Similarity	NPC474418
0.7752	Intermediate Similarity	NPC243196
0.7752	Intermediate Similarity	NPC142066
0.7752	Intermediate Similarity	NPC471354
0.7752	Intermediate Similarity	NPC471351
0.7752	Intermediate Similarity	NPC196429
0.7752	Intermediate Similarity	NPC309034
0.7752	Intermediate Similarity	NPC34390
0.7752	Intermediate Similarity	NPC152615
0.7752	Intermediate Similarity	NPC77319
0.7752	Intermediate Similarity	NPC157376
0.7752	Intermediate Similarity	NPC471355
0.7752	Intermediate Similarity	NPC473852
0.7752	Intermediate Similarity	NPC99728
0.7752	Intermediate Similarity	NPC50305
0.7752	Intermediate Similarity	NPC290693
0.7744	Intermediate Similarity	NPC3381
0.7737	Intermediate Similarity	NPC88668
0.7734	Intermediate Similarity	NPC84949
0.7734	Intermediate Similarity	NPC31354
0.7734	Intermediate Similarity	NPC69576
0.7734	Intermediate Similarity	NPC471633
0.7727	Intermediate Similarity	NPC153700
0.7727	Intermediate Similarity	NPC269642
0.7727	Intermediate Similarity	NPC107493
0.7727	Intermediate Similarity	NPC471082
0.7727	Intermediate Similarity	NPC193893
0.7727	Intermediate Similarity	NPC88326
0.7724	Intermediate Similarity	NPC161775
0.7721	Intermediate Similarity	NPC173347
0.7717	Intermediate Similarity	NPC470025
0.7717	Intermediate Similarity	NPC328074
0.7717	Intermediate Similarity	NPC321272
0.7717	Intermediate Similarity	NPC317460
0.771	Intermediate Similarity	NPC72260
0.771	Intermediate Similarity	NPC470312
0.771	Intermediate Similarity	NPC475629
0.771	Intermediate Similarity	NPC475556
0.771	Intermediate Similarity	NPC474370
0.7704	Intermediate Similarity	NPC470850
0.7704	Intermediate Similarity	NPC245094
0.7698	Intermediate Similarity	NPC177047
0.7692	Intermediate Similarity	NPC475372
0.7692	Intermediate Similarity	NPC83287
0.7687	Intermediate Similarity	NPC174367
0.7687	Intermediate Similarity	NPC47113
0.7681	Intermediate Similarity	NPC478072
0.7681	Intermediate Similarity	NPC471234
0.7669	Intermediate Similarity	NPC27363
0.7669	Intermediate Similarity	NPC41129
0.7669	Intermediate Similarity	NPC469789
0.7664	Intermediate Similarity	NPC471855
0.7656	Intermediate Similarity	NPC470027
0.7652	Intermediate Similarity	NPC233500
0.7652	Intermediate Similarity	NPC475419
0.7652	Intermediate Similarity	NPC314535
0.7652	Intermediate Similarity	NPC312481
0.7652	Intermediate Similarity	NPC476204
0.7652	Intermediate Similarity	NPC170084
0.7652	Intermediate Similarity	NPC474908
0.7652	Intermediate Similarity	NPC475590
0.7652	Intermediate Similarity	NPC129434
0.7652	Intermediate Similarity	NPC120390
0.7652	Intermediate Similarity	NPC470418
0.7652	Intermediate Similarity	NPC173555
0.7652	Intermediate Similarity	NPC202051
0.7647	Intermediate Similarity	NPC86159
0.7647	Intermediate Similarity	NPC471359
0.7647	Intermediate Similarity	NPC180079
0.7647	Intermediate Similarity	NPC9499
0.7647	Intermediate Similarity	NPC284406
0.7647	Intermediate Similarity	NPC469752
0.7647	Intermediate Similarity	NPC10823
0.7647	Intermediate Similarity	NPC219085
0.7647	Intermediate Similarity	NPC469754
0.7647	Intermediate Similarity	NPC470880
0.7647	Intermediate Similarity	NPC251866
0.7647	Intermediate Similarity	NPC17896
0.7647	Intermediate Similarity	NPC89514
0.7647	Intermediate Similarity	NPC70542
0.7647	Intermediate Similarity	NPC6108
0.7647	Intermediate Similarity	NPC471352
0.7647	Intermediate Similarity	NPC197707
0.7647	Intermediate Similarity	NPC469753
0.7647	Intermediate Similarity	NPC104382
0.7647	Intermediate Similarity	NPC471358
0.7647	Intermediate Similarity	NPC469755
0.7647	Intermediate Similarity	NPC469751
0.7647	Intermediate Similarity	NPC471360
0.7647	Intermediate Similarity	NPC471361
0.7639	Intermediate Similarity	NPC48813
0.7639	Intermediate Similarity	NPC194854
0.7638	Intermediate Similarity	NPC470076
0.7638	Intermediate Similarity	NPC17791
0.7634	Intermediate Similarity	NPC477071
0.7634	Intermediate Similarity	NPC219656
0.7634	Intermediate Similarity	NPC312536
0.7634	Intermediate Similarity	NPC329905
0.7634	Intermediate Similarity	NPC264954
0.763	Intermediate Similarity	NPC470882
0.763	Intermediate Similarity	NPC473265
0.763	Intermediate Similarity	NPC240070
0.763	Intermediate Similarity	NPC329784
0.763	Intermediate Similarity	NPC473253
0.763	Intermediate Similarity	NPC298841
0.7622	Intermediate Similarity	NPC471171
0.7619	Intermediate Similarity	NPC257853
0.7615	Intermediate Similarity	NPC475323
0.7615	Intermediate Similarity	NPC473656
0.7612	Intermediate Similarity	NPC8369
0.7609	Intermediate Similarity	NPC32793
0.7609	Intermediate Similarity	NPC247190

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 NPC60150 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	1850
0.2-0.3	4022
0.3-0.4	2093
0.4-0.5	559
0.5-0.6	277
0.6-0.7	89
0.7-0.8	12
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
0.7786	Intermediate Similarity	NPD8033	Approved
0.771	Intermediate Similarity	NPD8294	Approved
0.771	Intermediate Similarity	NPD8377	Approved
0.7692	Intermediate Similarity	NPD7327	Approved
0.7692	Intermediate Similarity	NPD7328	Approved
0.7652	Intermediate Similarity	NPD8296	Approved
0.7652	Intermediate Similarity	NPD8380	Approved
0.7652	Intermediate Similarity	NPD8335	Approved
0.7652	Intermediate Similarity	NPD8378	Approved
0.7652	Intermediate Similarity	NPD7503	Approved
0.7652	Intermediate Similarity	NPD8379	Approved
0.7647	Intermediate Similarity	NPD7319	Approved
0.7634	Intermediate Similarity	NPD7516	Approved
0.7556	Intermediate Similarity	NPD7507	Approved
0.7481	Intermediate Similarity	NPD7115	Discovery
0.7372	Intermediate Similarity	NPD7078	Approved
0.7226	Intermediate Similarity	NPD7492	Approved
0.7194	Intermediate Similarity	NPD7736	Approved
0.7185	Intermediate Similarity	NPD6054	Approved
0.7177	Intermediate Similarity	NPD4225	Approved
0.7174	Intermediate Similarity	NPD6616	Approved
0.7132	Intermediate Similarity	NPD6686	Approved
0.7122	Intermediate Similarity	NPD8293	Discontinued
0.712	Intermediate Similarity	NPD7640	Approved
0.712	Intermediate Similarity	NPD7639	Approved
0.708	Intermediate Similarity	NPD6370	Approved
0.7059	Intermediate Similarity	NPD6319	Approved
0.7059	Intermediate Similarity	NPD6059	Approved
0.704	Intermediate Similarity	NPD7638	Approved
0.704	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6371	Approved
0.7007	Intermediate Similarity	NPD8517	Approved
0.7007	Intermediate Similarity	NPD8516	Approved
0.7007	Intermediate Similarity	NPD8513	Phase 3
0.7007	Intermediate Similarity	NPD6015	Approved
0.7007	Intermediate Similarity	NPD8515	Approved
0.7007	Intermediate Similarity	NPD6016	Approved
0.6957	Remote Similarity	NPD5988	Approved
0.6947	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6882	Approved
0.6917	Remote Similarity	NPD8297	Approved
0.6842	Remote Similarity	NPD6649	Approved
0.6842	Remote Similarity	NPD6650	Approved
0.6838	Remote Similarity	NPD6009	Approved
0.6818	Remote Similarity	NPD6373	Approved
0.6818	Remote Similarity	NPD6372	Approved
0.6797	Remote Similarity	NPD5344	Discontinued
0.6794	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD6412	Phase 2
0.6794	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6053	Discontinued
0.6761	Remote Similarity	NPD8074	Phase 3
0.6742	Remote Similarity	NPD7320	Approved
0.6741	Remote Similarity	NPD8133	Approved
0.6741	Remote Similarity	NPD4632	Approved
0.6719	Remote Similarity	NPD6648	Approved
0.6718	Remote Similarity	NPD6008	Approved
0.6692	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD8328	Phase 3
0.6617	Remote Similarity	NPD6881	Approved
0.6617	Remote Similarity	NPD6899	Approved
0.6615	Remote Similarity	NPD7632	Discontinued
0.6613	Remote Similarity	NPD7838	Discovery
0.6597	Remote Similarity	NPD6033	Approved
0.6593	Remote Similarity	NPD8130	Phase 1
0.6591	Remote Similarity	NPD6675	Approved
0.6591	Remote Similarity	NPD7128	Approved
0.6591	Remote Similarity	NPD6402	Approved
0.6591	Remote Similarity	NPD5739	Approved
0.656	Remote Similarity	NPD7637	Suspended
0.6541	Remote Similarity	NPD5697	Approved
0.6519	Remote Similarity	NPD7290	Approved
0.6519	Remote Similarity	NPD4634	Approved
0.6519	Remote Similarity	NPD7102	Approved
0.6519	Remote Similarity	NPD6883	Approved
0.6516	Remote Similarity	NPD7625	Phase 1
0.6475	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6847	Approved
0.6471	Remote Similarity	NPD6869	Approved
0.6471	Remote Similarity	NPD6617	Approved
0.6444	Remote Similarity	NPD6014	Approved
0.6444	Remote Similarity	NPD6013	Approved
0.6444	Remote Similarity	NPD6012	Approved
0.6418	Remote Similarity	NPD5701	Approved
0.6408	Remote Similarity	NPD5983	Phase 2
0.6406	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6399	Phase 3
0.637	Remote Similarity	NPD6011	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.6351	Remote Similarity	NPD7260	Phase 2
0.635	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD6336	Discontinued
0.6328	Remote Similarity	NPD6001	Approved
0.6319	Remote Similarity	NPD6067	Discontinued
0.6316	Remote Similarity	NPD7799	Discontinued
0.6308	Remote Similarity	NPD6083	Phase 2
0.6308	Remote Similarity	NPD6084	Phase 2
0.6299	Remote Similarity	NPD5281	Approved
0.6299	Remote Similarity	NPD5284	Approved
0.6284	Remote Similarity	NPD5956	Approved
0.6279	Remote Similarity	NPD5695	Phase 3
0.6269	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5778	Approved
0.624	Remote Similarity	NPD7524	Approved
0.6232	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.622	Remote Similarity	NPD46	Approved
0.622	Remote Similarity	NPD6698	Approved
0.622	Remote Similarity	NPD5785	Approved
0.6212	Remote Similarity	NPD5285	Approved
0.6212	Remote Similarity	NPD5286	Approved
0.6212	Remote Similarity	NPD4696	Approved
0.62	Remote Similarity	NPD6845	Suspended
0.6183	Remote Similarity	NPD7902	Approved
0.6183	Remote Similarity	NPD4755	Approved
0.6172	Remote Similarity	NPD7983	Approved
0.617	Remote Similarity	NPD6274	Approved
0.6154	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD7100	Approved
0.6144	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6051	Approved
0.6136	Remote Similarity	NPD5696	Approved
0.6129	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD4202	Approved
0.6119	Remote Similarity	NPD5224	Approved
0.6119	Remote Similarity	NPD5225	Approved
0.6119	Remote Similarity	NPD5226	Approved
0.6119	Remote Similarity	NPD4633	Approved
0.6094	Remote Similarity	NPD5207	Approved
0.609	Remote Similarity	NPD4700	Approved
0.6084	Remote Similarity	NPD6335	Approved
0.608	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD5174	Approved
0.6074	Remote Similarity	NPD5175	Approved
0.6069	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6903	Approved
0.6048	Remote Similarity	NPD6695	Phase 3
0.6047	Remote Similarity	NPD6411	Approved
0.6047	Remote Similarity	NPD8035	Phase 2
0.6047	Remote Similarity	NPD6050	Approved
0.6047	Remote Similarity	NPD8034	Phase 2
0.6045	Remote Similarity	NPD5223	Approved
0.6014	Remote Similarity	NPD6317	Approved
0.6014	Remote Similarity	NPD4729	Approved
0.6014	Remote Similarity	NPD4730	Approved
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD7830	Approved
0.5986	Remote Similarity	NPD7829	Approved
0.5985	Remote Similarity	NPD4767	Approved
0.5985	Remote Similarity	NPD4768	Approved
0.5984	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7750	Discontinued
0.5972	Remote Similarity	NPD6314	Approved
0.5972	Remote Similarity	NPD6313	Approved
0.5969	Remote Similarity	NPD5692	Phase 3
0.5959	Remote Similarity	NPD6908	Approved
0.5959	Remote Similarity	NPD6909	Approved
0.5954	Remote Similarity	NPD7900	Approved
0.5954	Remote Similarity	NPD7748	Approved
0.5954	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5933	Remote Similarity	NPD8337	Approved
0.5933	Remote Similarity	NPD8336	Approved
0.5929	Remote Similarity	NPD5248	Approved
0.5929	Remote Similarity	NPD5249	Phase 3
0.5929	Remote Similarity	NPD5247	Approved
0.5929	Remote Similarity	NPD5250	Approved
0.5929	Remote Similarity	NPD5251	Approved
0.5926	Remote Similarity	NPD4159	Approved
0.5923	Remote Similarity	NPD6079	Approved
0.5923	Remote Similarity	NPD5694	Approved
0.5923	Remote Similarity	NPD5693	Phase 1
0.5909	Remote Similarity	NPD4629	Approved
0.5909	Remote Similarity	NPD5210	Approved
0.5906	Remote Similarity	NPD5330	Approved
0.5906	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD3618	Phase 1
0.5906	Remote Similarity	NPD7146	Approved
0.5906	Remote Similarity	NPD6684	Approved
0.5906	Remote Similarity	NPD6409	Approved
0.5906	Remote Similarity	NPD7334	Approved
0.5906	Remote Similarity	NPD7521	Approved
0.5899	Remote Similarity	NPD5128	Approved
0.5897	Remote Similarity	NPD6334	Approved
0.5897	Remote Similarity	NPD6333	Approved
0.5891	Remote Similarity	NPD4753	Phase 2
0.5891	Remote Similarity	NPD5328	Approved
0.5891	Remote Similarity	NPD6101	Approved
0.5891	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8338	Approved
0.5865	Remote Similarity	NPD4697	Phase 3
0.5859	Remote Similarity	NPD4251	Approved
0.5859	Remote Similarity	NPD4250	Approved
0.585	Remote Similarity	NPD6921	Approved
0.5839	Remote Similarity	NPD4754	Approved
0.5828	Remote Similarity	NPD7236	Approved
0.5827	Remote Similarity	NPD5363	Approved
0.5822	Remote Similarity	NPD4522	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