NPASS Compound

Structure

CID251236 OpenBabel06191716052D 38 42 0 0 1 0 0 0 0 0999 V2000 0.4943 3.0348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0468 -3.2252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4695 3.3016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1615 0.7322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2162 -0.3476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8242 2.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0766 2.1263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2460 -2.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4911 -1.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1883 0.1404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4712 -2.4075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3781 2.8839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7739 -1.7541 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6605 -1.8832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7938 -1.0362 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1644 0.0086 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1809 -0.5069 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6621 -0.5119 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5702 0.1404 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3578 -1.2298 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2611 0.7222 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4443 -1.2150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2325 0.4942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6546 1.3102 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3594 -1.1653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8793 1.0915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3793 -0.4473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1941 3.4619 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6565 -1.9728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7866 -0.3004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9334 -0.4121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5735 1.2731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2489 -1.9358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2282 0.5867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8793 1.0915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1621 -1.4505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8148 -0.4144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4706 1.8882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 7 24 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 15 1 0 0 0 0 10 35 1 0 0 0 0 11 13 1 0 0 0 0 12 28 2 0 0 0 0 12 38 1 0 0 0 0 13 25 1 6 0 0 0 14 20 1 0 0 0 0 14 29 2 0 0 0 0 15 27 1 6 0 0 0 15 36 1 0 0 0 0 16 18 1 0 0 0 0 16 21 1 0 0 0 0 16 30 1 6 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 17 37 1 1 0 0 0 18 25 1 6 0 0 0 18 27 1 0 0 0 0 19 26 1 6 0 0 0 19 27 1 0 0 0 0 20 25 1 6 0 0 0 20 31 1 0 0 0 0 21 26 1 1 0 0 0 21 32 1 0 0 0 0 22 33 2 0 0 0 0 22 36 1 0 0 0 0 23 24 1 0 0 0 0 23 34 2 0 0 0 0 23 37 1 0 0 0 0 24 4 1 1 0 0 0 24 38 1 0 0 0 0 25 5 1 6 0 0 0 26 6 1 1 0 0 0 26 35 1 0 0 0 0 27 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.23
Volume:	516.276
LogP:	1.368
LogD:	0.57
LogS:	-4.284
# Rotatable Bonds:	6
TPSA:	162.73
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.292
Synthetic Accessibility Score:	6.738
Fsp3:	0.815
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.309
MDCK Permeability:	0.00010653967183316126
Pgp-inhibitor:	0.998
Pgp-substrate:	0.083
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.092
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.309
Plasma Protein Binding (PPB):	33.38153076171875%
Volume Distribution (VD):	0.339
Pgp-substrate:	44.26106643676758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.632
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.553
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.398
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	4.011
Half-life (T1/2):	0.095

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.237
Drug-inuced Liver Injury (DILI):	0.855
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.232
Maximum Recommended Daily Dose:	0.093
Skin Sensitization:	0.188
Carcinogencity:	0.257
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.377

Download Data

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

Natural Product: NPC251236

Natural Product ID:	NPC251236
*Common Name:**	Quassimarin
IUPAC Name:	n.a.
Synonyms:	Quassimarin
Standard InCHIKey:	FXMIXHYJCNZLFE-ZXNWRKIUSA-N
Standard InCHI:	InChI=1S/C27H36O11/c1-7-24(4,38-12(3)28)23(34)37-17-19-26(6)21(32)16(30)18-25(5)13(11(2)8-14(29)20(25)31)9-15(36-22(17)33)27(18,19)10-35-26/h8,13,15-21,30-32H,7,9-10H2,1-6H3/t13-,15+,16+,17+,18+,19-,20+,21-,24-,25-,26-,27+/m0/s1
SMILES:	CC[C@@](C(=O)O[C@H]1C(=O)O[C@H]2[C@]34[C@@H]1[C@](C)(OC3)[C@@H](O)[C@@H]([C@@H]4[C@@]1([C@@H](C2)C(=CC(=O)[C@H]1O)C)C)O)(OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444177
PubChem CID:	44566234
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[12232058]
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16730421]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21648406]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7546	Prunus domestica	Species	Rosaceae	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
EC50	1
ED50	6
IC50	2
Others	1

Activity Type	# Activity
Cell Line	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	60.0	nM	PMID[543067]
NPT116	Cell Line	HL-60	Homo sapiens	EC50	=	90.0	nM	PMID[543067]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	130.0	nM	PMID[543067]
NPT116	Cell Line	HL-60	Homo sapiens	Ratio IC50	=	2.2	n.a.	PMID[543067]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.06	ug ml-1	PMID[543068]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.03	ug ml-1	PMID[543068]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	=	0.012	ug ml-1	PMID[543068]
NPT308	Cell Line	CAKI-1	Homo sapiens	ED50	=	0.05	ug ml-1	PMID[543068]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	0.006	ug ml-1	PMID[543068]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	0.05	ug ml-1	PMID[543068]

☑ 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 NPC251236 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	246
0.1-0.2	1404
0.2-0.3	4402
0.3-0.4	7747
0.4-0.5	12119
0.5-0.6	7045
0.6-0.7	5366
0.7-0.8	3736
0.8-0.85	472
0.85-0.9	76
0.9-0.95	64
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC96312
1.0	High Similarity	NPC328374
1.0	High Similarity	NPC40632
0.9906	High Similarity	NPC473798
0.9811	High Similarity	NPC49451
0.9633	High Similarity	NPC17772
0.963	High Similarity	NPC152199
0.963	High Similarity	NPC134869
0.963	High Similarity	NPC235539
0.9541	High Similarity	NPC474654
0.9541	High Similarity	NPC470854
0.9541	High Similarity	NPC97908
0.9541	High Similarity	NPC122033
0.9541	High Similarity	NPC287343
0.9537	High Similarity	NPC18547
0.9537	High Similarity	NPC474906
0.9455	High Similarity	NPC297179
0.945	High Similarity	NPC474734
0.9369	High Similarity	NPC470777
0.9364	High Similarity	NPC473590
0.9352	High Similarity	NPC289312
0.9352	High Similarity	NPC11252
0.9352	High Similarity	NPC474516
0.934	High Similarity	NPC293850
0.9279	High Similarity	NPC204552
0.9279	High Similarity	NPC188667
0.9273	High Similarity	NPC173686
0.9273	High Similarity	NPC16081
0.9266	High Similarity	NPC208998
0.9266	High Similarity	NPC7921
0.9259	High Similarity	NPC201992
0.9245	High Similarity	NPC144854
0.9245	High Similarity	NPC3316
0.9211	High Similarity	NPC18945
0.9211	High Similarity	NPC67251
0.9211	High Similarity	NPC265557
0.9211	High Similarity	NPC91693
0.9211	High Similarity	NPC105926
0.9204	High Similarity	NPC477046
0.9204	High Similarity	NPC102822
0.9182	High Similarity	NPC268238
0.9182	High Similarity	NPC143268
0.9182	High Similarity	NPC323821
0.9182	High Similarity	NPC45218
0.9159	High Similarity	NPC192813
0.9159	High Similarity	NPC154608
0.9159	High Similarity	NPC277017
0.913	High Similarity	NPC476729
0.913	High Similarity	NPC24651
0.9123	High Similarity	NPC312833
0.9115	High Similarity	NPC109607
0.9115	High Similarity	NPC107338
0.9115	High Similarity	NPC112038
0.9107	High Similarity	NPC470776
0.9107	High Similarity	NPC251310
0.9099	High Similarity	NPC207217
0.9099	High Similarity	NPC474046
0.9099	High Similarity	NPC470628
0.9099	High Similarity	NPC259306
0.9091	High Similarity	NPC51978
0.9083	High Similarity	NPC146945
0.9083	High Similarity	NPC171888
0.9035	High Similarity	NPC470779
0.9027	High Similarity	NPC475775
0.9027	High Similarity	NPC469488
0.9027	High Similarity	NPC476529
0.9018	High Similarity	NPC176513
0.9018	High Similarity	NPC470775
0.9009	High Similarity	NPC470919
0.9009	High Similarity	NPC469877
0.8972	High Similarity	NPC102352
0.8966	High Similarity	NPC470922
0.8899	High Similarity	NPC27814
0.8879	High Similarity	NPC227397
0.8879	High Similarity	NPC65523
0.885	High Similarity	NPC309433
0.8829	High Similarity	NPC472002
0.8829	High Similarity	NPC302146
0.8829	High Similarity	NPC90769
0.8818	High Similarity	NPC210005
0.8796	High Similarity	NPC181357
0.8793	High Similarity	NPC222688
0.8761	High Similarity	NPC179626
0.875	High Similarity	NPC198539
0.875	High Similarity	NPC194100
0.8739	High Similarity	NPC188291
0.8727	High Similarity	NPC141350
0.8727	High Similarity	NPC310546
0.8707	High Similarity	NPC275675
0.8684	High Similarity	NPC473968
0.8684	High Similarity	NPC146432
0.8684	High Similarity	NPC470778
0.8679	High Similarity	NPC472972
0.8678	High Similarity	NPC100390
0.8678	High Similarity	NPC254614
0.8661	High Similarity	NPC280782
0.8655	High Similarity	NPC476008
0.8644	High Similarity	NPC473255
0.8636	High Similarity	NPC94942
0.8611	High Similarity	NPC275583
0.8596	High Similarity	NPC213084
0.8596	High Similarity	NPC89929
0.8596	High Similarity	NPC190185
0.8584	High Similarity	NPC94509
0.8583	High Similarity	NPC295220
0.8583	High Similarity	NPC475636
0.8571	High Similarity	NPC477745
0.8571	High Similarity	NPC157476
0.8571	High Similarity	NPC285091
0.8571	High Similarity	NPC87662
0.8559	High Similarity	NPC472534
0.8559	High Similarity	NPC143706
0.8545	High Similarity	NPC230541
0.8545	High Similarity	NPC59530
0.8534	High Similarity	NPC127530
0.8534	High Similarity	NPC473920
0.8534	High Similarity	NPC279143
0.8532	High Similarity	NPC475036
0.8525	High Similarity	NPC102316
0.8512	High Similarity	NPC54614
0.8512	High Similarity	NPC309096
0.8509	High Similarity	NPC243354
0.8509	High Similarity	NPC299849
0.8509	High Similarity	NPC247069
0.8509	High Similarity	NPC117712
0.85	High Similarity	NPC470780
0.85	High Similarity	NPC470882
0.8482	Intermediate Similarity	NPC100908
0.8482	Intermediate Similarity	NPC474567
0.848	Intermediate Similarity	NPC596
0.8475	Intermediate Similarity	NPC65858
0.8475	Intermediate Similarity	NPC471965
0.8468	Intermediate Similarity	NPC262813
0.8462	Intermediate Similarity	NPC478051
0.8462	Intermediate Similarity	NPC109973
0.8462	Intermediate Similarity	NPC471406
0.8455	Intermediate Similarity	NPC477877
0.8435	Intermediate Similarity	NPC266728
0.8435	Intermediate Similarity	NPC49492
0.8421	Intermediate Similarity	NPC250109
0.8421	Intermediate Similarity	NPC477266
0.8421	Intermediate Similarity	NPC194273
0.8421	Intermediate Similarity	NPC471204
0.8421	Intermediate Similarity	NPC25909
0.8421	Intermediate Similarity	NPC962
0.8421	Intermediate Similarity	NPC255017
0.8417	Intermediate Similarity	NPC181999
0.8417	Intermediate Similarity	NPC225049
0.8407	Intermediate Similarity	NPC469655
0.8407	Intermediate Similarity	NPC469656
0.8407	Intermediate Similarity	NPC34315
0.8407	Intermediate Similarity	NPC188738
0.8407	Intermediate Similarity	NPC471243
0.8407	Intermediate Similarity	NPC474846
0.8403	Intermediate Similarity	NPC267822
0.8403	Intermediate Similarity	NPC471961
0.8403	Intermediate Similarity	NPC471964
0.8403	Intermediate Similarity	NPC202666
0.8403	Intermediate Similarity	NPC43252
0.8403	Intermediate Similarity	NPC14617
0.8403	Intermediate Similarity	NPC135038
0.8403	Intermediate Similarity	NPC478066
0.8403	Intermediate Similarity	NPC262199
0.84	Intermediate Similarity	NPC141215
0.84	Intermediate Similarity	NPC190065
0.84	Intermediate Similarity	NPC251998
0.84	Intermediate Similarity	NPC471089
0.8393	Intermediate Similarity	NPC41405
0.8393	Intermediate Similarity	NPC474242
0.839	Intermediate Similarity	NPC75417
0.8378	Intermediate Similarity	NPC202524
0.8378	Intermediate Similarity	NPC293512
0.8376	Intermediate Similarity	NPC475041
0.8376	Intermediate Similarity	NPC319570
0.8374	Intermediate Similarity	NPC33378
0.8374	Intermediate Similarity	NPC254146
0.8374	Intermediate Similarity	NPC6274
0.8374	Intermediate Similarity	NPC471855
0.8364	Intermediate Similarity	NPC471293
0.8364	Intermediate Similarity	NPC301787
0.8362	Intermediate Similarity	NPC477116
0.8362	Intermediate Similarity	NPC27999
0.8361	Intermediate Similarity	NPC264192
0.8348	Intermediate Similarity	NPC475633
0.8348	Intermediate Similarity	NPC102088
0.8347	Intermediate Similarity	NPC473265
0.8333	Intermediate Similarity	NPC295885
0.8333	Intermediate Similarity	NPC234042
0.8333	Intermediate Similarity	NPC471963
0.8333	Intermediate Similarity	NPC177820
0.8333	Intermediate Similarity	NPC193948
0.8333	Intermediate Similarity	NPC471962
0.8333	Intermediate Similarity	NPC152117
0.8333	Intermediate Similarity	NPC30188
0.8333	Intermediate Similarity	NPC247315
0.8333	Intermediate Similarity	NPC269530
0.8333	Intermediate Similarity	NPC140045
0.8333	Intermediate Similarity	NPC470477
0.8333	Intermediate Similarity	NPC169818
0.8319	Intermediate Similarity	NPC5284

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 NPC251236 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	1669
0.2-0.3	3844
0.3-0.4	2165
0.4-0.5	720
0.5-0.6	265
0.6-0.7	130
0.7-0.8	122
0.8-0.85	27
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8403	Intermediate Similarity	NPD8328	Phase 3
0.8393	Intermediate Similarity	NPD6372	Approved
0.8393	Intermediate Similarity	NPD6373	Approved
0.8333	Intermediate Similarity	NPD8297	Approved
0.8305	Intermediate Similarity	NPD6319	Approved
0.8288	Intermediate Similarity	NPD6675	Approved
0.8288	Intermediate Similarity	NPD7128	Approved
0.8288	Intermediate Similarity	NPD6402	Approved
0.8288	Intermediate Similarity	NPD5739	Approved
0.8246	Intermediate Similarity	NPD6649	Approved
0.8246	Intermediate Similarity	NPD6650	Approved
0.8142	Intermediate Similarity	NPD7320	Approved
0.8142	Intermediate Similarity	NPD6899	Approved
0.8142	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8142	Intermediate Similarity	NPD6881	Approved
0.8103	Intermediate Similarity	NPD4632	Approved
0.8053	Intermediate Similarity	NPD5697	Approved
0.8053	Intermediate Similarity	NPD5701	Approved
0.8051	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8033	Intermediate Similarity	NPD7492	Approved
0.8017	Intermediate Similarity	NPD6882	Approved
0.8	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD7290	Approved
0.8	Intermediate Similarity	NPD6054	Approved
0.8	Intermediate Similarity	NPD6883	Approved
0.8	Intermediate Similarity	NPD6059	Approved
0.7984	Intermediate Similarity	NPD7736	Approved
0.7967	Intermediate Similarity	NPD6616	Approved
0.7931	Intermediate Similarity	NPD6617	Approved
0.7931	Intermediate Similarity	NPD6847	Approved
0.7931	Intermediate Similarity	NPD6869	Approved
0.7931	Intermediate Similarity	NPD8130	Phase 1
0.7913	Intermediate Similarity	NPD6014	Approved
0.7913	Intermediate Similarity	NPD6012	Approved
0.7913	Intermediate Similarity	NPD6013	Approved
0.7913	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD8293	Discontinued
0.7903	Intermediate Similarity	NPD7078	Approved
0.7899	Intermediate Similarity	NPD6009	Approved
0.7869	Intermediate Similarity	NPD6370	Approved
0.7826	Intermediate Similarity	NPD6011	Approved
0.7807	Intermediate Similarity	NPD6008	Approved
0.7805	Intermediate Similarity	NPD7604	Phase 2
0.7787	Intermediate Similarity	NPD5983	Phase 2
0.7787	Intermediate Similarity	NPD6016	Approved
0.7787	Intermediate Similarity	NPD6015	Approved
0.7778	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD6412	Phase 2
0.7724	Intermediate Similarity	NPD5988	Approved
0.7692	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6336	Discontinued
0.768	Intermediate Similarity	NPD7507	Approved
0.7658	Intermediate Similarity	NPD4755	Approved
0.7658	Intermediate Similarity	NPD7902	Approved
0.7658	Intermediate Similarity	NPD6084	Phase 2
0.7658	Intermediate Similarity	NPD6083	Phase 2
0.7638	Intermediate Similarity	NPD7319	Approved
0.7603	Intermediate Similarity	NPD7115	Discovery
0.7545	Intermediate Similarity	NPD7748	Approved
0.7542	Intermediate Similarity	NPD4634	Approved
0.7523	Intermediate Similarity	NPD7515	Phase 2
0.7522	Intermediate Similarity	NPD5286	Approved
0.7522	Intermediate Similarity	NPD4700	Approved
0.7522	Intermediate Similarity	NPD4696	Approved
0.7522	Intermediate Similarity	NPD5285	Approved
0.7521	Intermediate Similarity	NPD6274	Approved
0.7521	Intermediate Similarity	NPD6686	Approved
0.75	Intermediate Similarity	NPD6921	Approved
0.748	Intermediate Similarity	NPD7101	Approved
0.748	Intermediate Similarity	NPD7100	Approved
0.7455	Intermediate Similarity	NPD6399	Phase 3
0.7436	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD5696	Approved
0.7422	Intermediate Similarity	NPD6033	Approved
0.7411	Intermediate Similarity	NPD4697	Phase 3
0.7398	Intermediate Similarity	NPD6335	Approved
0.7391	Intermediate Similarity	NPD4633	Approved
0.7391	Intermediate Similarity	NPD5224	Approved
0.7391	Intermediate Similarity	NPD5225	Approved
0.7391	Intermediate Similarity	NPD5211	Phase 2
0.7391	Intermediate Similarity	NPD5226	Approved
0.7387	Intermediate Similarity	NPD7900	Approved
0.7387	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6908	Approved
0.736	Intermediate Similarity	NPD6909	Approved
0.735	Intermediate Similarity	NPD4767	Approved
0.735	Intermediate Similarity	NPD4768	Approved
0.7339	Intermediate Similarity	NPD7516	Approved
0.7339	Intermediate Similarity	NPD5328	Approved
0.7328	Intermediate Similarity	NPD5175	Approved
0.7328	Intermediate Similarity	NPD5174	Approved
0.7321	Intermediate Similarity	NPD5695	Phase 3
0.7317	Intermediate Similarity	NPD6317	Approved
0.7315	Intermediate Similarity	NPD3573	Approved
0.7304	Intermediate Similarity	NPD5223	Approved
0.7281	Intermediate Similarity	NPD7638	Approved
0.7281	Intermediate Similarity	NPD4225	Approved
0.7265	Intermediate Similarity	NPD5141	Approved
0.7258	Intermediate Similarity	NPD7327	Approved
0.7258	Intermediate Similarity	NPD6313	Approved
0.7258	Intermediate Similarity	NPD7328	Approved
0.7258	Intermediate Similarity	NPD6314	Approved
0.7257	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5221	Approved
0.7257	Intermediate Similarity	NPD5222	Approved
0.7248	Intermediate Similarity	NPD6672	Approved
0.7248	Intermediate Similarity	NPD5737	Approved
0.7236	Intermediate Similarity	NPD6868	Approved
0.7227	Intermediate Similarity	NPD4730	Approved
0.7227	Intermediate Similarity	NPD4729	Approved
0.7222	Intermediate Similarity	NPD3618	Phase 1
0.7222	Intermediate Similarity	NPD8513	Phase 3
0.7222	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8516	Approved
0.7222	Intermediate Similarity	NPD8515	Approved
0.7222	Intermediate Similarity	NPD8517	Approved
0.7217	Intermediate Similarity	NPD7639	Approved
0.7217	Intermediate Similarity	NPD7640	Approved
0.7207	Intermediate Similarity	NPD6079	Approved
0.7193	Intermediate Similarity	NPD5173	Approved
0.7179	Intermediate Similarity	NPD4754	Approved
0.7107	Intermediate Similarity	NPD5251	Approved
0.7107	Intermediate Similarity	NPD5247	Approved
0.7107	Intermediate Similarity	NPD5248	Approved
0.7107	Intermediate Similarity	NPD5249	Phase 3
0.7107	Intermediate Similarity	NPD5250	Approved
0.7087	Intermediate Similarity	NPD8378	Approved
0.7087	Intermediate Similarity	NPD8335	Approved
0.7087	Intermediate Similarity	NPD8380	Approved
0.7087	Intermediate Similarity	NPD8296	Approved
0.7087	Intermediate Similarity	NPD8033	Approved
0.7087	Intermediate Similarity	NPD8379	Approved
0.7083	Intermediate Similarity	NPD5128	Approved
0.708	Intermediate Similarity	NPD5282	Discontinued
0.7073	Intermediate Similarity	NPD8133	Approved
0.7054	Intermediate Similarity	NPD6411	Approved
0.7049	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6673	Approved
0.7027	Intermediate Similarity	NPD4753	Phase 2
0.7027	Intermediate Similarity	NPD6080	Approved
0.7027	Intermediate Similarity	NPD6904	Approved
0.7018	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD8377	Approved
0.7008	Intermediate Similarity	NPD8294	Approved
0.6992	Remote Similarity	NPD7260	Phase 2
0.6991	Remote Similarity	NPD4202	Approved
0.6964	Remote Similarity	NPD6698	Approved
0.6964	Remote Similarity	NPD46	Approved
0.6953	Remote Similarity	NPD7503	Approved
0.6937	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5215	Approved
0.6911	Remote Similarity	NPD5216	Approved
0.6911	Remote Similarity	NPD5217	Approved
0.6909	Remote Similarity	NPD7146	Approved
0.6909	Remote Similarity	NPD6684	Approved
0.6909	Remote Similarity	NPD7521	Approved
0.6909	Remote Similarity	NPD7334	Approved
0.6909	Remote Similarity	NPD6409	Approved
0.6909	Remote Similarity	NPD5330	Approved
0.6903	Remote Similarity	NPD8035	Phase 2
0.6903	Remote Similarity	NPD8034	Phase 2
0.6881	Remote Similarity	NPD4786	Approved
0.6875	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6101	Approved
0.687	Remote Similarity	NPD5210	Approved
0.687	Remote Similarity	NPD4629	Approved
0.6864	Remote Similarity	NPD5344	Discontinued
0.686	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6053	Discontinued
0.6852	Remote Similarity	NPD3667	Approved
0.6846	Remote Similarity	NPD6067	Discontinued
0.6829	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5169	Approved
0.6829	Remote Similarity	NPD5135	Approved
0.6818	Remote Similarity	NPD8074	Phase 3
0.6815	Remote Similarity	NPD6845	Suspended
0.6786	Remote Similarity	NPD6903	Approved
0.6774	Remote Similarity	NPD5127	Approved
0.6757	Remote Similarity	NPD6098	Approved
0.6754	Remote Similarity	NPD6050	Approved
0.6754	Remote Similarity	NPD5693	Phase 1
0.6727	Remote Similarity	NPD3665	Phase 1
0.6727	Remote Similarity	NPD3666	Approved
0.6727	Remote Similarity	NPD3133	Approved
0.6696	Remote Similarity	NPD5779	Approved
0.6696	Remote Similarity	NPD5778	Approved
0.6694	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD5956	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD5692	Phase 3
0.6667	Remote Similarity	NPD5168	Approved
0.6638	Remote Similarity	NPD6001	Approved
0.6614	Remote Similarity	NPD5167	Approved
0.6609	Remote Similarity	NPD5694	Approved
0.6609	Remote Similarity	NPD5281	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