NPASS Compound

Structure

NPC48992 OpenBabel07101719152D 43 47 0 0 1 0 0 0 0 0999 V2000 -2.2011 -4.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6705 -4.8009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9839 1.9155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9250 0.5048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0379 3.6938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5812 4.1979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9541 -1.6638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4436 -0.8159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5646 -0.7018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4645 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3124 1.6317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6166 1.6317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3124 0.6527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8035 -3.1104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3581 -2.3035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2327 0.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2082 2.5436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4131 -2.2631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4394 -2.3655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3549 0.8289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4559 1.8242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5917 -0.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2250 -3.9941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0472 0.9385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0828 3.4785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9366 -1.4198 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6166 0.6527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4645 0.1631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6166 -1.3055 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7687 0.1631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8129 0.9406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8200 0.1618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8527 -0.3019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4645 -0.8159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0411 -1.4710 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5405 0.2855 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1648 0.8894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7687 -0.8159 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0792 0.6527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1397 1.8635 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6658 0.8154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0311 -1.2646 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 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 7 34 1 0 0 0 0 8 34 1 0 0 0 0 9 35 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 27 2 0 0 0 0 13 28 2 0 0 0 0 14 15 1 0 0 0 0 14 23 2 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 24 2 0 0 0 0 17 21 1 0 0 0 0 17 25 2 0 0 0 0 18 19 1 0 0 0 0 18 29 1 0 0 0 0 19 35 1 0 0 0 0 22 26 1 0 0 0 0 22 36 1 0 0 0 0 26 35 1 1 0 0 0 27 28 1 0 0 0 0 27 30 1 0 0 0 0 28 34 1 0 0 0 0 29 34 1 0 0 0 0 29 38 1 1 0 0 0 30 39 2 0 0 0 0 31 36 1 0 0 0 0 31 37 1 0 0 0 0 31 40 2 0 0 0 0 32 37 1 0 0 0 0 32 38 1 0 0 0 0 32 41 2 0 0 0 0 33 36 1 0 0 0 0 33 42 2 0 0 0 0 33 43 1 0 0 0 0 35 38 1 6 0 0 0 36 20 1 1 0 0 0 37 21 1 1 0 0 0 37 43 1 0 0 0 0 38 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.35
Volume:	640.608
LogP:	8.545
LogD:	6.042
LogS:	-5.409
# Rotatable Bonds:	6
TPSA:	77.51
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.192
Synthetic Accessibility Score:	6.384
Fsp3:	0.579
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.062
MDCK Permeability:	2.2578788048122078e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.215
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.809
30% Bioavailability (F30%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.514
Plasma Protein Binding (PPB):	86.989501953125%
Volume Distribution (VD):	2.709
Pgp-substrate:	6.447229385375977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.419
CYP2C19-inhibitor:	0.591
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.5
CYP2C9-substrate:	0.1
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.895
CYP3A4-substrate:	0.926

ADMET: Excretion

Clearance (CL):	13.213
Half-life (T1/2):	0.01

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.781
AMES Toxicity:	0.462
Rat Oral Acute Toxicity:	0.916
Maximum Recommended Daily Dose:	0.685
Skin Sensitization:	0.536
Carcinogencity:	0.568
Eye Corrosion:	0.01
Eye Irritation:	0.07
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC48992

Natural Product ID:	NPC48992
*Common Name:**	FPHBKYRPWQOBBF-PPXCZVBLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FPHBKYRPWQOBBF-PPXCZVBLSA-N
Standard InCHI:	InChI=1S/C38H48O5/c1-23(2)14-15-26-22-36(20-16-24(3)4)31(40)37(43-33(36)42,21-17-25(5)6)32(41)38-29(18-19-35(26,38)9)34(7,8)28-13-11-10-12-27(28)30(38)39/h10-14,16-17,26,29H,15,18-22H2,1-9H3/t26-,29+,35+,36+,37+,38+/m0/s1
SMILES:	CC(=CC[C@H]1C[C@@]2(CC=C(C)C)C(=O)O[C@](C2=O)(C(=O)[C@]23[C@]1(C)CC[C@@H]3C(c1c(C2=O)cccc1)(C)C)CC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581571
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	aerial parts	Yunnan, China	n.a.	PMID[25871261]
NPO40864	Hypericum uralum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26583263]
NPO40864	Hypericum uralum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27148858]
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19915	Hypericum henryi	Species	Hypericaceae	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	5
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	16000.0	nM	PMID[475832]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	25500.0	nM	PMID[475832]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	12200.0	nM	PMID[475832]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	-100.0	%	PMID[475832]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	24100.0	nM	PMID[475832]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[475832]

☑ 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 NPC48992 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	345
0.1-0.2	1446
0.2-0.3	2838
0.3-0.4	10187
0.4-0.5	17048
0.5-0.6	9433
0.6-0.7	1297
0.7-0.8	100
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.916	High Similarity	NPC94425
0.8095	Intermediate Similarity	NPC268930
0.8095	Intermediate Similarity	NPC61651
0.8031	Intermediate Similarity	NPC472698
0.8031	Intermediate Similarity	NPC472697
0.803	Intermediate Similarity	NPC470648
0.8015	Intermediate Similarity	NPC472693
0.8015	Intermediate Similarity	NPC472694
0.7985	Intermediate Similarity	NPC471832
0.797	Intermediate Similarity	NPC472678
0.7939	Intermediate Similarity	NPC328107
0.7937	Intermediate Similarity	NPC260886
0.7926	Intermediate Similarity	NPC472682
0.7926	Intermediate Similarity	NPC472692
0.792	Intermediate Similarity	NPC130591
0.792	Intermediate Similarity	NPC234637
0.7907	Intermediate Similarity	NPC476225
0.7903	Intermediate Similarity	NPC280789
0.784	Intermediate Similarity	NPC471481
0.7836	Intermediate Similarity	NPC316553
0.7778	Intermediate Similarity	NPC294458
0.776	Intermediate Similarity	NPC218855
0.7724	Intermediate Similarity	NPC472696
0.7724	Intermediate Similarity	NPC472683
0.7724	Intermediate Similarity	NPC472695
0.7724	Intermediate Similarity	NPC472701
0.7698	Intermediate Similarity	NPC93287
0.7692	Intermediate Similarity	NPC202015
0.7687	Intermediate Similarity	NPC328997
0.7687	Intermediate Similarity	NPC294050
0.7671	Intermediate Similarity	NPC473403
0.7669	Intermediate Similarity	NPC325740
0.7669	Intermediate Similarity	NPC318067
0.7664	Intermediate Similarity	NPC470278
0.7664	Intermediate Similarity	NPC471334
0.7642	Intermediate Similarity	NPC85560
0.7642	Intermediate Similarity	NPC244933
0.7642	Intermediate Similarity	NPC472699
0.7642	Intermediate Similarity	NPC472700
0.7638	Intermediate Similarity	NPC471721
0.763	Intermediate Similarity	NPC146239
0.7554	Intermediate Similarity	NPC144257
0.7537	Intermediate Similarity	NPC8990
0.7537	Intermediate Similarity	NPC85511
0.7534	Intermediate Similarity	NPC475552
0.7519	Intermediate Similarity	NPC167323
0.7519	Intermediate Similarity	NPC269923
0.7518	Intermediate Similarity	NPC477358
0.75	Intermediate Similarity	NPC326664
0.75	Intermediate Similarity	NPC473243
0.75	Intermediate Similarity	NPC241851
0.7483	Intermediate Similarity	NPC251294
0.7481	Intermediate Similarity	NPC477369
0.7465	Intermediate Similarity	NPC184109
0.7465	Intermediate Similarity	NPC86772
0.7464	Intermediate Similarity	NPC42234
0.7448	Intermediate Similarity	NPC82467
0.7445	Intermediate Similarity	NPC51448
0.7445	Intermediate Similarity	NPC115797
0.7444	Intermediate Similarity	NPC476234
0.7442	Intermediate Similarity	NPC215419
0.7429	Intermediate Similarity	NPC472656
0.7426	Intermediate Similarity	NPC476599
0.7426	Intermediate Similarity	NPC470649
0.7426	Intermediate Similarity	NPC478107
0.7424	Intermediate Similarity	NPC204784
0.7422	Intermediate Similarity	NPC469547
0.7413	Intermediate Similarity	NPC276652
0.7413	Intermediate Similarity	NPC272523
0.7413	Intermediate Similarity	NPC325805
0.7398	Intermediate Similarity	NPC474866
0.7398	Intermediate Similarity	NPC471829
0.7398	Intermediate Similarity	NPC472691
0.7398	Intermediate Similarity	NPC475939
0.7397	Intermediate Similarity	NPC80895
0.7397	Intermediate Similarity	NPC471912
0.7385	Intermediate Similarity	NPC62138
0.7376	Intermediate Similarity	NPC203486
0.7372	Intermediate Similarity	NPC51292
0.7361	Intermediate Similarity	NPC475660
0.736	Intermediate Similarity	NPC37914
0.736	Intermediate Similarity	NPC100767
0.7357	Intermediate Similarity	NPC469499
0.7357	Intermediate Similarity	NPC477360
0.7347	Intermediate Similarity	NPC471100
0.7347	Intermediate Similarity	NPC301946
0.7347	Intermediate Similarity	NPC277053
0.7347	Intermediate Similarity	NPC471107
0.7344	Intermediate Similarity	NPC292834
0.7339	Intermediate Similarity	NPC329282
0.7338	Intermediate Similarity	NPC122504
0.7338	Intermediate Similarity	NPC3450
0.7329	Intermediate Similarity	NPC153214
0.7324	Intermediate Similarity	NPC265459
0.7324	Intermediate Similarity	NPC475262
0.7324	Intermediate Similarity	NPC290833
0.7324	Intermediate Similarity	NPC79699
0.7324	Intermediate Similarity	NPC270364
0.7319	Intermediate Similarity	NPC268607
0.731	Intermediate Similarity	NPC473654
0.731	Intermediate Similarity	NPC473497
0.731	Intermediate Similarity	NPC187566
0.7308	Intermediate Similarity	NPC476357
0.7303	Intermediate Similarity	NPC21410
0.7303	Intermediate Similarity	NPC473670
0.7297	Intermediate Similarity	NPC477095
0.7297	Intermediate Similarity	NPC170668
0.7287	Intermediate Similarity	NPC477475
0.7287	Intermediate Similarity	NPC143768
0.7287	Intermediate Similarity	NPC477476
0.7279	Intermediate Similarity	NPC472681
0.7279	Intermediate Similarity	NPC472704
0.7273	Intermediate Similarity	NPC222968
0.7273	Intermediate Similarity	NPC194769
0.7273	Intermediate Similarity	NPC80605
0.7273	Intermediate Similarity	NPC323440
0.7273	Intermediate Similarity	NPC285221
0.7267	Intermediate Similarity	NPC125033
0.7267	Intermediate Similarity	NPC254558
0.7266	Intermediate Similarity	NPC137315
0.726	Intermediate Similarity	NPC475135
0.7255	Intermediate Similarity	NPC217091
0.7254	Intermediate Similarity	NPC329913
0.7254	Intermediate Similarity	NPC477368
0.7254	Intermediate Similarity	NPC472250
0.7254	Intermediate Similarity	NPC4242
0.7254	Intermediate Similarity	NPC153617
0.7254	Intermediate Similarity	NPC471911
0.7252	Intermediate Similarity	NPC9274
0.7248	Intermediate Similarity	NPC205389
0.7246	Intermediate Similarity	NPC473423
0.7244	Intermediate Similarity	NPC192577
0.7244	Intermediate Similarity	NPC55744
0.7239	Intermediate Similarity	NPC472679
0.7239	Intermediate Similarity	NPC472680
0.7234	Intermediate Similarity	NPC209851
0.7234	Intermediate Similarity	NPC472394
0.723	Intermediate Similarity	NPC471162
0.7226	Intermediate Similarity	NPC295664
0.7222	Intermediate Similarity	NPC475373
0.7219	Intermediate Similarity	NPC51602
0.7214	Intermediate Similarity	NPC475671
0.7214	Intermediate Similarity	NPC475452
0.7214	Intermediate Similarity	NPC25736
0.7214	Intermediate Similarity	NPC272946
0.7211	Intermediate Similarity	NPC477094
0.7211	Intermediate Similarity	NPC45307
0.7211	Intermediate Similarity	NPC477096
0.7208	Intermediate Similarity	NPC472393
0.7206	Intermediate Similarity	NPC472703
0.7203	Intermediate Similarity	NPC232888
0.7203	Intermediate Similarity	NPC477367
0.7197	Intermediate Similarity	NPC469843
0.7194	Intermediate Similarity	NPC477370
0.7192	Intermediate Similarity	NPC475413
0.7192	Intermediate Similarity	NPC474303
0.7183	Intermediate Similarity	NPC477364
0.7176	Intermediate Similarity	NPC470764
0.7174	Intermediate Similarity	NPC477363
0.7174	Intermediate Similarity	NPC477366
0.7172	Intermediate Similarity	NPC118366
0.7153	Intermediate Similarity	NPC469742
0.7153	Intermediate Similarity	NPC51079
0.7153	Intermediate Similarity	NPC477362
0.7152	Intermediate Similarity	NPC25484
0.7152	Intermediate Similarity	NPC232583
0.7143	Intermediate Similarity	NPC37968
0.7143	Intermediate Similarity	NPC63737
0.7143	Intermediate Similarity	NPC183540
0.7133	Intermediate Similarity	NPC126516
0.7133	Intermediate Similarity	NPC477359
0.7132	Intermediate Similarity	NPC265513
0.7131	Intermediate Similarity	NPC226041
0.7123	Intermediate Similarity	NPC475400
0.7122	Intermediate Similarity	NPC477365
0.7122	Intermediate Similarity	NPC474106
0.7122	Intermediate Similarity	NPC477357
0.7121	Intermediate Similarity	NPC149691
0.712	Intermediate Similarity	NPC329556
0.712	Intermediate Similarity	NPC247976
0.7113	Intermediate Similarity	NPC475493
0.7111	Intermediate Similarity	NPC474223
0.7111	Intermediate Similarity	NPC232958
0.7111	Intermediate Similarity	NPC105709
0.7111	Intermediate Similarity	NPC475827
0.7105	Intermediate Similarity	NPC471103
0.7101	Intermediate Similarity	NPC478108
0.7099	Intermediate Similarity	NPC307651
0.7097	Intermediate Similarity	NPC225079
0.7097	Intermediate Similarity	NPC264728
0.7097	Intermediate Similarity	NPC109514
0.7095	Intermediate Similarity	NPC131966
0.7095	Intermediate Similarity	NPC191387
0.7092	Intermediate Similarity	NPC475508
0.7092	Intermediate Similarity	NPC147561
0.709	Intermediate Similarity	NPC318173
0.7083	Intermediate Similarity	NPC59677
0.7083	Intermediate Similarity	NPC472247
0.708	Intermediate Similarity	NPC474159
0.708	Intermediate Similarity	NPC474254

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 NPC48992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	889
0.2-0.3	1897
0.3-0.4	3424
0.4-0.5	1934
0.5-0.6	636
0.6-0.7	67
0.7-0.8	2
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
0.7868	Intermediate Similarity	NPD7961	Discontinued
0.771	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD7094	Approved
0.7422	Intermediate Similarity	NPD6858	Approved
0.7273	Intermediate Similarity	NPD7610	Discontinued
0.723	Intermediate Similarity	NPD7236	Approved
0.712	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1930	Approved
0.712	Intermediate Similarity	NPD1929	Approved
0.709	Intermediate Similarity	NPD7009	Phase 2
0.7016	Intermediate Similarity	NPD2066	Phase 3
0.7	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7239	Suspended
0.6992	Remote Similarity	NPD3495	Discontinued
0.6985	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7631	Approved
0.6942	Remote Similarity	NPD1508	Approved
0.6917	Remote Similarity	NPD5951	Approved
0.6905	Remote Similarity	NPD1932	Approved
0.6892	Remote Similarity	NPD1471	Phase 3
0.687	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7609	Phase 3
0.6853	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2329	Discontinued
0.6829	Remote Similarity	NPD7799	Discontinued
0.6828	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4766	Approved
0.6774	Remote Similarity	NPD1843	Approved
0.6748	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD2182	Approved
0.6694	Remote Similarity	NPD1693	Approved
0.6692	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7305	Phase 1
0.6643	Remote Similarity	NPD6287	Discontinued
0.6643	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.664	Remote Similarity	NPD1989	Approved
0.6619	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7058	Phase 2
0.6584	Remote Similarity	NPD7057	Phase 3
0.6552	Remote Similarity	NPD7055	Discontinued
0.6544	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD2629	Approved
0.6541	Remote Similarity	NPD2067	Discontinued
0.6541	Remote Similarity	NPD1317	Discontinued
0.6538	Remote Similarity	NPD164	Approved
0.6532	Remote Similarity	NPD1088	Approved
0.6531	Remote Similarity	NPD8032	Phase 2
0.6529	Remote Similarity	NPD650	Approved
0.6529	Remote Similarity	NPD1087	Approved
0.6522	Remote Similarity	NPD6065	Approved
0.6516	Remote Similarity	NPD7478	Approved
0.6503	Remote Similarity	NPD1876	Approved
0.6483	Remote Similarity	NPD7084	Phase 3
0.6479	Remote Similarity	NPD6637	Approved
0.6462	Remote Similarity	NPD6647	Phase 2
0.6454	Remote Similarity	NPD4879	Approved
0.6453	Remote Similarity	NPD8407	Phase 2
0.6452	Remote Similarity	NPD6050	Approved
0.6452	Remote Similarity	NPD5694	Approved
0.6429	Remote Similarity	NPD3025	Approved
0.6429	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3024	Approved
0.6423	Remote Similarity	NPD6904	Approved
0.6423	Remote Similarity	NPD6673	Approved
0.6423	Remote Similarity	NPD6080	Approved
0.6419	Remote Similarity	NPD6663	Approved
0.6412	Remote Similarity	NPD5909	Discontinued
0.6402	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7008	Discontinued
0.6392	Remote Similarity	NPD7606	Phase 3
0.6379	Remote Similarity	NPD8434	Phase 2
0.6377	Remote Similarity	NPD3317	Approved
0.6374	Remote Similarity	NPD8368	Discontinued
0.6371	Remote Similarity	NPD3673	Approved
0.6371	Remote Similarity	NPD5692	Phase 3
0.6371	Remote Similarity	NPD5207	Approved
0.6371	Remote Similarity	NPD1090	Approved
0.6371	Remote Similarity	NPD1089	Approved
0.6371	Remote Similarity	NPD1086	Approved
0.6371	Remote Similarity	NPD3672	Approved
0.6357	Remote Similarity	NPD7798	Approved
0.6351	Remote Similarity	NPD3764	Approved
0.635	Remote Similarity	NPD2650	Approved
0.635	Remote Similarity	NPD2652	Approved
0.6349	Remote Similarity	NPD1202	Approved
0.6349	Remote Similarity	NPD1563	Approved
0.6341	Remote Similarity	NPD5737	Approved
0.6341	Remote Similarity	NPD6672	Approved
0.634	Remote Similarity	NPD2346	Discontinued
0.6338	Remote Similarity	NPD3023	Approved
0.6338	Remote Similarity	NPD3026	Approved
0.6316	Remote Similarity	NPD6685	Approved
0.6316	Remote Similarity	NPD2799	Discontinued
0.6316	Remote Similarity	NPD6614	Approved
0.629	Remote Similarity	NPD800	Approved
0.6279	Remote Similarity	NPD5696	Approved
0.6268	Remote Similarity	NPD2932	Approved
0.6268	Remote Similarity	NPD3019	Approved
0.6268	Remote Similarity	NPD2345	Approved
0.6259	Remote Similarity	NPD5736	Approved
0.6259	Remote Similarity	NPD4198	Discontinued
0.625	Remote Similarity	NPD3972	Approved
0.6231	Remote Similarity	NPD1238	Approved
0.6226	Remote Similarity	NPD6273	Approved
0.6211	Remote Similarity	NPD3226	Approved
0.6202	Remote Similarity	NPD1564	Approved
0.6202	Remote Similarity	NPD1566	Phase 3
0.6202	Remote Similarity	NPD1565	Approved
0.619	Remote Similarity	NPD1239	Approved
0.619	Remote Similarity	NPD6085	Phase 2
0.619	Remote Similarity	NPD5693	Phase 1
0.619	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD6765	Approved
0.6185	Remote Similarity	NPD6764	Approved
0.6181	Remote Similarity	NPD5618	Discontinued
0.6179	Remote Similarity	NPD6098	Approved
0.6176	Remote Similarity	NPD4234	Approved
0.6176	Remote Similarity	NPD4233	Approved
0.6172	Remote Similarity	NPD6049	Phase 2
0.6172	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD942	Approved
0.6165	Remote Similarity	NPD1237	Approved
0.616	Remote Similarity	NPD5346	Phase 2
0.616	Remote Similarity	NPD5347	Phase 2
0.6138	Remote Similarity	NPD4878	Approved
0.6133	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD2313	Discontinued
0.6129	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD4479	Discontinued
0.6124	Remote Similarity	NPD8435	Approved
0.6122	Remote Similarity	NPD1470	Approved
0.6115	Remote Similarity	NPD7487	Discontinued
0.6115	Remote Similarity	NPD6010	Discontinued
0.6115	Remote Similarity	NPD8166	Discontinued
0.6115	Remote Similarity	NPD7076	Approved
0.6115	Remote Similarity	NPD7077	Approved
0.609	Remote Similarity	NPD5765	Approved
0.6084	Remote Similarity	NPD1245	Approved
0.6081	Remote Similarity	NPD2798	Approved
0.6077	Remote Similarity	NPD6084	Phase 2
0.6077	Remote Similarity	NPD6083	Phase 2
0.6074	Remote Similarity	NPD6599	Discontinued
0.6071	Remote Similarity	NPD1246	Approved
0.6069	Remote Similarity	NPD4806	Approved
0.6069	Remote Similarity	NPD4807	Approved
0.6058	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.605	Remote Similarity	NPD227	Approved
0.605	Remote Similarity	NPD225	Approved
0.6048	Remote Similarity	NPD9257	Approved
0.6048	Remote Similarity	NPD9259	Approved
0.6047	Remote Similarity	NPD5654	Approved
0.6047	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD6784	Approved
0.6045	Remote Similarity	NPD6785	Approved
0.6042	Remote Similarity	NPD5306	Approved
0.6042	Remote Similarity	NPD5305	Approved
0.6034	Remote Similarity	NPD8360	Approved
0.6034	Remote Similarity	NPD8361	Approved
0.6029	Remote Similarity	NPD6899	Approved
0.6029	Remote Similarity	NPD6881	Approved
0.6026	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD8130	Phase 1
0.6014	Remote Similarity	NPD6649	Approved
0.6014	Remote Similarity	NPD6650	Approved
0.6014	Remote Similarity	NPD7741	Discontinued
0.6014	Remote Similarity	NPD3266	Approved
0.6014	Remote Similarity	NPD3267	Approved
0.6013	Remote Similarity	NPD7003	Approved
0.6012	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5048	Discontinued
0.6	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6832	Phase 2
0.6	Remote Similarity	NPD4793	Discontinued
0.6	Remote Similarity	NPD9490	Approved
0.5987	Remote Similarity	NPD7713	Phase 3
0.5972	Remote Similarity	NPD4102	Approved
0.5972	Remote Similarity	NPD4105	Approved
0.5971	Remote Similarity	NPD6912	Phase 3
0.5971	Remote Similarity	NPD8297	Approved
0.597	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD6001	Approved
0.5964	Remote Similarity	NPD5761	Phase 2
0.5964	Remote Similarity	NPD5760	Phase 2
0.5964	Remote Similarity	NPD7819	Suspended
0.5962	Remote Similarity	NPD5406	Approved
0.5962	Remote Similarity	NPD5408	Approved
0.5962	Remote Similarity	NPD5404	Approved
0.5962	Remote Similarity	NPD5405	Approved
0.5959	Remote Similarity	NPD2609	Approved
0.5959	Remote Similarity	NPD1201	Approved
0.5959	Remote Similarity	NPD4218	Approved
0.5959	Remote Similarity	NPD2612	Approved
0.5959	Remote Similarity	NPD3131	Approved
0.5959	Remote Similarity	NPD2610	Approved
0.5959	Remote Similarity	NPD3132	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