NPASS Compound

Structure

CID148740 OpenBabel06191715522D 34 38 0 0 1 0 0 0 0 0999 V2000 -1.3537 -1.9936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5366 -1.4629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9606 6.1646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0107 5.9478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4605 4.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7765 4.0546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5364 4.6260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0007 0.4829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2240 1.7029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0678 2.1901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1192 2.6773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0678 5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4047 0.7157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6234 3.2610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6734 3.0442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4535 3.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2240 4.6260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7157 1.4047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3802 2.1901 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4535 1.8890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9116 4.6260 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0678 3.1645 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9624 -0.1524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0461 4.1388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4047 -1.0206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6734 5.2335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9116 3.6517 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3802 3.1645 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2240 3.6517 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1524 0.9624 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0205 4.1388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3777 -1.0716 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 5.6234 5.0167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 11 1 1 0 0 0 20 30 1 0 0 0 0 21 26 1 0 0 0 0 21 27 1 1 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 25 1 6 0 0 0 23 33 1 0 0 0 0 24 31 2 0 0 0 0 24 34 1 0 0 0 0 25 32 1 0 0 0 0 26 34 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 8 1 6 0 0 0 30 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	517.178
LogP:	6.074
LogD:	5.009
LogS:	-4.866
# Rotatable Bonds:	2
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.454
Synthetic Accessibility Score:	4.88
Fsp3:	0.967
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.924
MDCK Permeability:	3.9235950680449605e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.57

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	94.68589782714844%
Volume Distribution (VD):	1.117
Pgp-substrate:	2.96463680267334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.285
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.95
CYP2C9-inhibitor:	0.156
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.379
CYP3A4-inhibitor:	0.339
CYP3A4-substrate:	0.406

ADMET: Excretion

Clearance (CL):	3.602
Half-life (T1/2):	0.143

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.276
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.18
Skin Sensitization:	0.951
Carcinogencity:	0.025
Eye Corrosion:	0.926
Eye Irritation:	0.229
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC148740

Natural Product ID:	NPC148740
*Common Name:**	ZHWDSUNHEWADAB-YUOZJKDKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZHWDSUNHEWADAB-YUOZJKDKSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-25(2,32)23-13-18-30(8,33-23)20-11-16-28(6)19(20)9-10-22-27(5)15-14-24(31)34-26(3,4)21(27)12-17-29(22,28)7/h19-23,32H,9-18H2,1-8H3/t19-,20+,21+,22-,23+,27+,28-,29-,30+/m1/s1
SMILES:	O=C1CC[C@]2([C@H](C(O1)(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@H]2[C@]1(C)CC[C@H](O1)C(O)(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651034
PubChem CID:	53318969
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	stem	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20939540]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21875098]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22817615]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24868863]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25089845]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28682072]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[29883114]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8578	Acacia rhodoxylon	Species	Fabaceae	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
ED50	1
IC50	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
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	uM	PMID[474589]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	20000.0	nM	PMID[474589]

☑ 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 NPC148740 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	351
0.1-0.2	3075
0.2-0.3	12349
0.3-0.4	11133
0.4-0.5	5635
0.5-0.6	7289
0.6-0.7	2474
0.7-0.8	358
0.8-0.85	18
0.85-0.9	9
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC102156
0.9487	High Similarity	NPC164289
0.9487	High Similarity	NPC242771
0.9487	High Similarity	NPC311642
0.9487	High Similarity	NPC100366
0.8861	High Similarity	NPC245029
0.8861	High Similarity	NPC31302
0.881	High Similarity	NPC48824
0.881	High Similarity	NPC229407
0.881	High Similarity	NPC250687
0.881	High Similarity	NPC254572
0.8706	High Similarity	NPC269267
0.8659	High Similarity	NPC217559
0.8659	High Similarity	NPC292458
0.8659	High Similarity	NPC268578
0.8571	High Similarity	NPC92139
0.8519	High Similarity	NPC472853
0.8506	High Similarity	NPC471747
0.8471	Intermediate Similarity	NPC239938
0.8415	Intermediate Similarity	NPC190940
0.8353	Intermediate Similarity	NPC474448
0.8353	Intermediate Similarity	NPC472745
0.8353	Intermediate Similarity	NPC80700
0.8315	Intermediate Similarity	NPC470424
0.8313	Intermediate Similarity	NPC286719
0.8313	Intermediate Similarity	NPC477936
0.8313	Intermediate Similarity	NPC477286
0.8272	Intermediate Similarity	NPC476732
0.8272	Intermediate Similarity	NPC199965
0.8256	Intermediate Similarity	NPC474174
0.8256	Intermediate Similarity	NPC251808
0.8228	Intermediate Similarity	NPC472945
0.8228	Intermediate Similarity	NPC472944
0.8214	Intermediate Similarity	NPC111582
0.8214	Intermediate Similarity	NPC477285
0.8214	Intermediate Similarity	NPC259173
0.8205	Intermediate Similarity	NPC469940
0.8193	Intermediate Similarity	NPC77311
0.8193	Intermediate Similarity	NPC58631
0.8171	Intermediate Similarity	NPC80891
0.8171	Intermediate Similarity	NPC201276
0.8161	Intermediate Similarity	NPC476435
0.8148	Intermediate Similarity	NPC180199
0.8148	Intermediate Similarity	NPC477919
0.814	Intermediate Similarity	NPC103782
0.814	Intermediate Similarity	NPC114378
0.8132	Intermediate Similarity	NPC116683
0.8095	Intermediate Similarity	NPC477935
0.8095	Intermediate Similarity	NPC121121
0.8049	Intermediate Similarity	NPC324700
0.8049	Intermediate Similarity	NPC80089
0.8049	Intermediate Similarity	NPC224802
0.8049	Intermediate Similarity	NPC171426
0.8049	Intermediate Similarity	NPC34046
0.7976	Intermediate Similarity	NPC12933
0.7955	Intermediate Similarity	NPC56777
0.7955	Intermediate Similarity	NPC471221
0.7955	Intermediate Similarity	NPC201607
0.7955	Intermediate Similarity	NPC255176
0.7955	Intermediate Similarity	NPC33398
0.7931	Intermediate Similarity	NPC477283
0.7931	Intermediate Similarity	NPC472272
0.7931	Intermediate Similarity	NPC155531
0.7931	Intermediate Similarity	NPC215968
0.7927	Intermediate Similarity	NPC477918
0.7927	Intermediate Similarity	NPC474404
0.7912	Intermediate Similarity	NPC206878
0.7912	Intermediate Similarity	NPC470423
0.7907	Intermediate Similarity	NPC291310
0.7907	Intermediate Similarity	NPC471044
0.7907	Intermediate Similarity	NPC473336
0.7901	Intermediate Similarity	NPC477934
0.7857	Intermediate Similarity	NPC261616
0.7848	Intermediate Similarity	NPC477929
0.7826	Intermediate Similarity	NPC215570
0.7816	Intermediate Similarity	NPC476715
0.7805	Intermediate Similarity	NPC477932
0.7805	Intermediate Similarity	NPC4209
0.7805	Intermediate Similarity	NPC477933
0.7791	Intermediate Similarity	NPC472744
0.7791	Intermediate Similarity	NPC470070
0.7778	Intermediate Similarity	NPC472146
0.7778	Intermediate Similarity	NPC185529
0.7778	Intermediate Similarity	NPC167702
0.7778	Intermediate Similarity	NPC55508
0.7778	Intermediate Similarity	NPC280026
0.7765	Intermediate Similarity	NPC232625
0.775	Intermediate Similarity	NPC197701
0.775	Intermediate Similarity	NPC478227
0.7738	Intermediate Similarity	NPC477287
0.7722	Intermediate Similarity	NPC476734
0.7722	Intermediate Similarity	NPC469941
0.7722	Intermediate Similarity	NPC252032
0.7722	Intermediate Similarity	NPC319671
0.7711	Intermediate Similarity	NPC207010
0.7711	Intermediate Similarity	NPC11907
0.7711	Intermediate Similarity	NPC212453
0.7711	Intermediate Similarity	NPC133596
0.7711	Intermediate Similarity	NPC264602
0.7711	Intermediate Similarity	NPC64081
0.7711	Intermediate Similarity	NPC474574
0.7711	Intermediate Similarity	NPC171658
0.7711	Intermediate Similarity	NPC317913
0.7701	Intermediate Similarity	NPC477434
0.7701	Intermediate Similarity	NPC65133
0.7692	Intermediate Similarity	NPC52756
0.7683	Intermediate Similarity	NPC270306
0.7683	Intermediate Similarity	NPC186851
0.7683	Intermediate Similarity	NPC91387
0.7683	Intermediate Similarity	NPC231680
0.7683	Intermediate Similarity	NPC212733
0.7674	Intermediate Similarity	NPC202688
0.7674	Intermediate Similarity	NPC60018
0.7674	Intermediate Similarity	NPC154043
0.7674	Intermediate Similarity	NPC289486
0.7674	Intermediate Similarity	NPC13494
0.7674	Intermediate Similarity	NPC61107
0.7667	Intermediate Similarity	NPC24705
0.7667	Intermediate Similarity	NPC56962
0.7667	Intermediate Similarity	NPC200580
0.7647	Intermediate Similarity	NPC470609
0.7647	Intermediate Similarity	NPC170038
0.7647	Intermediate Similarity	NPC472951
0.7647	Intermediate Similarity	NPC472943
0.764	Intermediate Similarity	NPC202937
0.7619	Intermediate Similarity	NPC471045
0.7619	Intermediate Similarity	NPC185465
0.7619	Intermediate Similarity	NPC329117
0.7614	Intermediate Similarity	NPC477445
0.7586	Intermediate Similarity	NPC2572
0.7586	Intermediate Similarity	NPC29342
0.7582	Intermediate Similarity	NPC470114
0.7582	Intermediate Similarity	NPC50443
0.7582	Intermediate Similarity	NPC18536
0.7564	Intermediate Similarity	NPC42060
0.7564	Intermediate Similarity	NPC477931
0.7564	Intermediate Similarity	NPC268736
0.7561	Intermediate Similarity	NPC472854
0.7561	Intermediate Similarity	NPC477930
0.7558	Intermediate Similarity	NPC470154
0.7556	Intermediate Similarity	NPC476379
0.7553	Intermediate Similarity	NPC476728
0.7551	Intermediate Similarity	NPC471293
0.7551	Intermediate Similarity	NPC100078
0.7529	Intermediate Similarity	NPC476176
0.7529	Intermediate Similarity	NPC81074
0.7529	Intermediate Similarity	NPC118987
0.7529	Intermediate Similarity	NPC220379
0.7529	Intermediate Similarity	NPC477282
0.7529	Intermediate Similarity	NPC320144
0.7528	Intermediate Similarity	NPC64862
0.7528	Intermediate Similarity	NPC476717
0.7528	Intermediate Similarity	NPC131365
0.7528	Intermediate Similarity	NPC475007
0.7526	Intermediate Similarity	NPC244969
0.7526	Intermediate Similarity	NPC213528
0.75	Intermediate Similarity	NPC18953
0.75	Intermediate Similarity	NPC64466
0.75	Intermediate Similarity	NPC476719
0.75	Intermediate Similarity	NPC298168
0.75	Intermediate Similarity	NPC473066
0.75	Intermediate Similarity	NPC196197
0.75	Intermediate Similarity	NPC473299
0.75	Intermediate Similarity	NPC178541
0.75	Intermediate Similarity	NPC167974
0.75	Intermediate Similarity	NPC307865
0.75	Intermediate Similarity	NPC471151
0.75	Intermediate Similarity	NPC319909
0.75	Intermediate Similarity	NPC143133
0.75	Intermediate Similarity	NPC169389
0.7475	Intermediate Similarity	NPC166079
0.7474	Intermediate Similarity	NPC253586
0.7474	Intermediate Similarity	NPC472273
0.7473	Intermediate Similarity	NPC61688
0.7471	Intermediate Similarity	NPC477447
0.7471	Intermediate Similarity	NPC477284
0.7471	Intermediate Similarity	NPC477446
0.7471	Intermediate Similarity	NPC470155
0.747	Intermediate Similarity	NPC27349
0.747	Intermediate Similarity	NPC472311
0.747	Intermediate Similarity	NPC24014
0.7468	Intermediate Similarity	NPC41542
0.7444	Intermediate Similarity	NPC5943
0.7444	Intermediate Similarity	NPC167877
0.7442	Intermediate Similarity	NPC477851
0.7442	Intermediate Similarity	NPC474714
0.7442	Intermediate Similarity	NPC1882
0.7442	Intermediate Similarity	NPC134227
0.7439	Intermediate Similarity	NPC109510
0.7423	Intermediate Similarity	NPC178853
0.7419	Intermediate Similarity	NPC472237
0.7419	Intermediate Similarity	NPC256104
0.7419	Intermediate Similarity	NPC472231
0.7419	Intermediate Similarity	NPC472232
0.7419	Intermediate Similarity	NPC182740
0.7419	Intermediate Similarity	NPC211845
0.7419	Intermediate Similarity	NPC472238
0.7419	Intermediate Similarity	NPC122083
0.7416	Intermediate Similarity	NPC266651
0.7416	Intermediate Similarity	NPC473350

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 NPC148740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	3411
0.2-0.3	3634
0.3-0.4	1016
0.4-0.5	305
0.5-0.6	302
0.6-0.7	85
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
0.8049	Intermediate Similarity	NPD6697	Approved
0.8049	Intermediate Similarity	NPD6115	Approved
0.8049	Intermediate Similarity	NPD6114	Approved
0.8049	Intermediate Similarity	NPD6118	Approved
0.7901	Intermediate Similarity	NPD3702	Approved
0.7805	Intermediate Similarity	NPD6117	Approved
0.7778	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6116	Phase 1
0.7531	Intermediate Similarity	NPD6081	Approved
0.7531	Intermediate Similarity	NPD5777	Approved
0.7436	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4224	Phase 2
0.7317	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4244	Approved
0.7195	Intermediate Similarity	NPD4245	Approved
0.7195	Intermediate Similarity	NPD4789	Approved
0.716	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5360	Phase 3
0.7073	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3698	Phase 2
0.7073	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3703	Phase 2
0.703	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8034	Phase 2
0.6947	Remote Similarity	NPD8035	Phase 2
0.69	Remote Similarity	NPD1700	Approved
0.6875	Remote Similarity	NPD6399	Phase 3
0.6867	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4758	Discontinued
0.6667	Remote Similarity	NPD6928	Phase 2
0.663	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3669	Approved
0.6629	Remote Similarity	NPD4238	Approved
0.6629	Remote Similarity	NPD5364	Discontinued
0.6629	Remote Similarity	NPD4802	Phase 2
0.66	Remote Similarity	NPD6083	Phase 2
0.66	Remote Similarity	NPD6084	Phase 2
0.6593	Remote Similarity	NPD1780	Approved
0.6593	Remote Similarity	NPD1779	Approved
0.6582	Remote Similarity	NPD3198	Approved
0.6531	Remote Similarity	NPD8171	Discontinued
0.6514	Remote Similarity	NPD8133	Approved
0.6471	Remote Similarity	NPD8418	Phase 2
0.6463	Remote Similarity	NPD7909	Approved
0.6458	Remote Similarity	NPD6672	Approved
0.6458	Remote Similarity	NPD6903	Approved
0.6458	Remote Similarity	NPD5737	Approved
0.6452	Remote Similarity	NPD4788	Approved
0.6444	Remote Similarity	NPD3671	Phase 1
0.6421	Remote Similarity	NPD7521	Approved
0.6421	Remote Similarity	NPD7334	Approved
0.6421	Remote Similarity	NPD6409	Approved
0.6421	Remote Similarity	NPD7146	Approved
0.6421	Remote Similarity	NPD6684	Approved
0.6421	Remote Similarity	NPD5330	Approved
0.6415	Remote Similarity	NPD6412	Phase 2
0.64	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5695	Phase 3
0.6396	Remote Similarity	NPD6940	Discontinued
0.6383	Remote Similarity	NPD4786	Approved
0.6373	Remote Similarity	NPD7638	Approved
0.6373	Remote Similarity	NPD5696	Approved
0.6364	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7320	Approved
0.6355	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7128	Approved
0.6321	Remote Similarity	NPD5739	Approved
0.6321	Remote Similarity	NPD6402	Approved
0.6321	Remote Similarity	NPD6008	Approved
0.6321	Remote Similarity	NPD6675	Approved
0.6311	Remote Similarity	NPD7640	Approved
0.6311	Remote Similarity	NPD7639	Approved
0.6296	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD6098	Approved
0.6239	Remote Similarity	NPD7492	Approved
0.6226	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6904	Approved
0.6224	Remote Similarity	NPD6673	Approved
0.6224	Remote Similarity	NPD6080	Approved
0.6207	Remote Similarity	NPD4787	Phase 1
0.6204	Remote Similarity	NPD6899	Approved
0.6204	Remote Similarity	NPD6881	Approved
0.6204	Remote Similarity	NPD6686	Approved
0.6195	Remote Similarity	NPD7115	Discovery
0.619	Remote Similarity	NPD7632	Discontinued
0.6186	Remote Similarity	NPD7524	Approved
0.6186	Remote Similarity	NPD6616	Approved
0.6186	Remote Similarity	NPD7507	Approved
0.6174	Remote Similarity	NPD6059	Approved
0.6174	Remote Similarity	NPD6054	Approved
0.6174	Remote Similarity	NPD6319	Approved
0.617	Remote Similarity	NPD3667	Approved
0.6154	Remote Similarity	NPD3730	Approved
0.6154	Remote Similarity	NPD3728	Approved
0.6147	Remote Similarity	NPD6373	Approved
0.6147	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6372	Approved
0.6139	Remote Similarity	NPD7748	Approved
0.6134	Remote Similarity	NPD8293	Discontinued
0.6134	Remote Similarity	NPD7078	Approved
0.6126	Remote Similarity	NPD6053	Discontinued
0.6111	Remote Similarity	NPD5697	Approved
0.6111	Remote Similarity	NPD5701	Approved
0.61	Remote Similarity	NPD7637	Suspended
0.6091	Remote Similarity	NPD7102	Approved
0.6091	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7290	Approved
0.6091	Remote Similarity	NPD6883	Approved
0.6083	Remote Similarity	NPD7736	Approved
0.6068	Remote Similarity	NPD6370	Approved
0.6061	Remote Similarity	NPD5328	Approved
0.6061	Remote Similarity	NPD4753	Phase 2
0.6055	Remote Similarity	NPD6011	Approved
0.6053	Remote Similarity	NPD6009	Approved
0.6042	Remote Similarity	NPD3133	Approved
0.6042	Remote Similarity	NPD3665	Phase 1
0.6042	Remote Similarity	NPD3666	Approved
0.6036	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6847	Approved
0.6036	Remote Similarity	NPD6617	Approved
0.6036	Remote Similarity	NPD8130	Phase 1
0.6036	Remote Similarity	NPD6650	Approved
0.6036	Remote Similarity	NPD6869	Approved
0.6036	Remote Similarity	NPD6649	Approved
0.6033	Remote Similarity	NPD7319	Approved
0.6017	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD4221	Approved
0.6	Remote Similarity	NPD4223	Phase 3
0.6	Remote Similarity	NPD1811	Approved
0.6	Remote Similarity	NPD5207	Approved
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD1810	Approved
0.6	Remote Similarity	NPD6012	Approved
0.5983	Remote Similarity	NPD6015	Approved
0.5983	Remote Similarity	NPD6016	Approved
0.5983	Remote Similarity	NPD5983	Phase 2
0.5982	Remote Similarity	NPD6882	Approved
0.598	Remote Similarity	NPD6001	Approved
0.5979	Remote Similarity	NPD5329	Approved
0.5977	Remote Similarity	NPD229	Approved
0.5962	Remote Similarity	NPD7902	Approved
0.596	Remote Similarity	NPD5208	Approved
0.5949	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6050	Approved
0.5941	Remote Similarity	NPD5693	Phase 1
0.5941	Remote Similarity	NPD7515	Phase 2
0.5941	Remote Similarity	NPD6079	Approved
0.5941	Remote Similarity	NPD5284	Approved
0.5941	Remote Similarity	NPD5281	Approved
0.5938	Remote Similarity	NPD6695	Phase 3
0.5932	Remote Similarity	NPD5988	Approved
0.5918	Remote Similarity	NPD3618	Phase 1
0.5917	Remote Similarity	NPD6336	Discontinued
0.5914	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD3617	Approved
0.5909	Remote Similarity	NPD3726	Approved
0.5909	Remote Similarity	NPD3725	Approved
0.5905	Remote Similarity	NPD4225	Approved
0.59	Remote Similarity	NPD6051	Approved
0.5895	Remote Similarity	NPD4139	Approved
0.5895	Remote Similarity	NPD4692	Approved
0.5882	Remote Similarity	NPD371	Approved
0.5882	Remote Similarity	NPD4202	Approved
0.5876	Remote Similarity	NPD4197	Approved
0.5876	Remote Similarity	NPD3668	Phase 3
0.5876	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6920	Discontinued
0.587	Remote Similarity	NPD6933	Approved
0.5862	Remote Similarity	NPD7327	Approved
0.5862	Remote Similarity	NPD7328	Approved
0.5843	Remote Similarity	NPD2254	Approved
0.5843	Remote Similarity	NPD2686	Approved
0.5843	Remote Similarity	NPD2687	Approved
0.5842	Remote Similarity	NPD5692	Phase 3
0.5833	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6052	Approved
0.582	Remote Similarity	NPD6033	Approved
0.5818	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7516	Approved
0.581	Remote Similarity	NPD4755	Approved
0.5804	Remote Similarity	NPD4634	Approved
0.58	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD6705	Phase 1
0.5789	Remote Similarity	NPD7525	Registered
0.5789	Remote Similarity	NPD2266	Phase 2
0.5784	Remote Similarity	NPD5694	Approved
0.5776	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD5362	Discontinued
0.5769	Remote Similarity	NPD5210	Approved
0.5769	Remote Similarity	NPD7991	Discontinued
0.5769	Remote Similarity	NPD4629	Approved
0.5763	Remote Similarity	NPD8377	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