NPASS Compound

Structure

NPC469854 OpenBabel07101718292D 46 48 0 0 1 0 0 0 0 0999 V2000 1.6682 5.1842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8674 3.9850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0881 -1.9584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2401 -3.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0473 2.6681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6083 4.3063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3584 -1.3376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3376 -1.3376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0248 -1.8717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1067 -2.2121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2292 3.5460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3921 -1.9584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2834 3.7994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0409 1.1819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3921 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8890 1.6715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8890 -0.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1556 2.1612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9653 -0.1643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9216 4.2384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2401 -2.4480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3549 3.3605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0409 0.2027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4090 3.1070 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6960 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7370 1.1819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7370 0.2027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3057 -1.0825 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.3449 0.2027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1929 -0.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.9554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7213 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2710 -1.2468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 1.4688 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5850 1.6715 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5850 -0.2869 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6807 -1.8363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1929 -1.2661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3128 1.3132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8672 -1.1907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 1.4688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8960 -0.4929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 23 2 0 0 0 0 6 23 1 0 0 0 0 7 35 1 0 0 0 0 8 35 1 0 0 0 0 9 36 1 0 0 0 0 10 36 1 0 0 0 0 11 13 1 0 0 0 0 11 21 2 0 0 0 0 12 15 1 0 0 0 0 12 22 2 0 0 0 0 14 16 2 0 0 0 0 14 24 1 0 0 0 0 16 27 1 0 0 0 0 17 24 2 0 0 0 0 17 28 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 19 37 1 0 0 0 0 20 29 1 0 0 0 0 23 25 1 0 0 0 0 24 31 1 0 0 0 0 25 13 1 6 0 0 0 26 15 1 6 0 0 0 26 35 1 0 0 0 0 27 28 2 0 0 0 0 27 39 1 0 0 0 0 28 40 1 0 0 0 0 29 36 1 0 0 0 0 29 41 1 0 0 0 0 30 31 1 0 0 0 0 30 32 2 0 0 0 0 30 33 1 0 0 0 0 31 42 2 0 0 0 0 32 37 1 0 0 0 0 32 43 1 0 0 0 0 33 38 1 0 0 0 0 33 44 2 0 0 0 0 34 37 1 0 0 0 0 34 38 1 0 0 0 0 34 45 2 0 0 0 0 35 38 1 0 0 0 0 36 46 1 0 0 0 0 37 18 1 6 0 0 0 38 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	636.37
Volume:	684.092
LogP:	6.348
LogD:	3.62
LogS:	-3.932
# Rotatable Bonds:	12
TPSA:	149.2
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.088
Synthetic Accessibility Score:	5.967
Fsp3:	0.579
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.305
MDCK Permeability:	1.1006889508280437e-05
Pgp-inhibitor:	0.371
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.42
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.274

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	97.8556137084961%
Volume Distribution (VD):	1.181
Pgp-substrate:	3.9953086376190186%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.131
CYP2C19-substrate:	0.365
CYP2C9-inhibitor:	0.54
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.311
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.876
CYP3A4-substrate:	0.769

ADMET: Excretion

Clearance (CL):	11.755
Half-life (T1/2):	0.215

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.291
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.927
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.037
Carcinogencity:	0.546
Eye Corrosion:	0.014
Eye Irritation:	0.121
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC469854

Natural Product ID:	NPC469854
*Common Name:**	HVKHAMACCIIGAM-CGJQWDJPSA-N
IUPAC Name:	n.a.
Synonyms:	18-Hydroxygarcimultifloroned
Standard InCHIKey:	HVKHAMACCIIGAM-CGJQWDJPSA-N
Standard InCHI:	InChI=1S/C38H52O8/c1-21(2)11-13-25(23(5)6)18-37-19-26(15-12-22(3)4)35(7,8)38(34(37)45,20-29(41)36(9,10)46)33(44)30(32(37)43)31(42)24-14-16-27(39)28(40)17-24/h11-12,14,16-17,25-26,29,39-41,43,46H,5,13,15,18-20H2,1-4,6-10H3/t25-,26-,29?,37-,38+/m1/s1
SMILES:	CC(=CC[C@@H](C(=C)C)C[C@@]12C[C@@H](CC=C(C)C)C([C@](C2=O)(C(=O)C(=C1O)C(=O)c1ccc(c(c1)O)O)CC(C(O)(C)C)O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215428
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	stems	n.a.	n.a.	PMID[12932126]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20681570]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	Twigs and leaves	Taichung, Taiwan	1993-Aug	PMID[9322359]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5049	Garcinia multiflora	Species	Clusiaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23000.0	nM	PMID[501127]
NPT2	Others	Unspecified		Ratio	>	3.0	n.a.	PMID[501127]

☑ 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 NPC469854 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	352
0.1-0.2	1311
0.2-0.3	2624
0.3-0.4	6729
0.4-0.5	11200
0.5-0.6	7334
0.6-0.7	10209
0.7-0.8	2815
0.8-0.85	60
0.85-0.9	15
0.9-0.95	18
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469856
0.9856	High Similarity	NPC471970
0.9854	High Similarity	NPC469855
0.9854	High Similarity	NPC471971
0.9854	High Similarity	NPC471972
0.9854	High Similarity	NPC30846
0.9635	High Similarity	NPC294330
0.9562	High Similarity	NPC477849
0.9562	High Similarity	NPC23667
0.9562	High Similarity	NPC46242
0.9562	High Similarity	NPC165191
0.9562	High Similarity	NPC157284
0.9562	High Similarity	NPC42384
0.9562	High Similarity	NPC297797
0.9562	High Similarity	NPC51531
0.9562	High Similarity	NPC28592
0.9562	High Similarity	NPC289358
0.9562	High Similarity	NPC114333
0.9562	High Similarity	NPC5014
0.9562	High Similarity	NPC50615
0.9562	High Similarity	NPC473779
0.9562	High Similarity	NPC245760
0.9562	High Similarity	NPC149773
0.9562	High Similarity	NPC469857
0.9562	High Similarity	NPC473479
0.9562	High Similarity	NPC91887
0.9441	High Similarity	NPC132810
0.9424	High Similarity	NPC473527
0.9416	High Similarity	NPC7464
0.9306	High Similarity	NPC46549
0.9306	High Similarity	NPC264229
0.9301	High Similarity	NPC273798
0.9296	High Similarity	NPC469375
0.9296	High Similarity	NPC8493
0.9296	High Similarity	NPC294679
0.9296	High Similarity	NPC145301
0.9296	High Similarity	NPC144247
0.9143	High Similarity	NPC471974
0.9143	High Similarity	NPC469680
0.9143	High Similarity	NPC469681
0.898	High Similarity	NPC237441
0.8905	High Similarity	NPC25736
0.8867	High Similarity	NPC305710
0.8667	High Similarity	NPC48949
0.8542	High Similarity	NPC118366
0.8521	High Similarity	NPC4170
0.8521	High Similarity	NPC474715
0.8521	High Similarity	NPC138472
0.8503	High Similarity	NPC248068
0.8493	Intermediate Similarity	NPC471853
0.8446	Intermediate Similarity	NPC199936
0.8414	Intermediate Similarity	NPC277559
0.8414	Intermediate Similarity	NPC475957
0.8392	Intermediate Similarity	NPC111845
0.8387	Intermediate Similarity	NPC471968
0.8367	Intermediate Similarity	NPC470035
0.8367	Intermediate Similarity	NPC476534
0.8356	Intermediate Similarity	NPC230811
0.8333	Intermediate Similarity	NPC470038
0.8333	Intermediate Similarity	NPC202225
0.831	Intermediate Similarity	NPC117609
0.8298	Intermediate Similarity	NPC234175
0.8288	Intermediate Similarity	NPC471152
0.8288	Intermediate Similarity	NPC49911
0.8278	Intermediate Similarity	NPC143685
0.8276	Intermediate Similarity	NPC43353
0.8276	Intermediate Similarity	NPC153088
0.8267	Intermediate Similarity	NPC79627
0.8264	Intermediate Similarity	NPC294226
0.8261	Intermediate Similarity	NPC86900
0.8255	Intermediate Similarity	NPC184935
0.8212	Intermediate Similarity	NPC258856
0.8182	Intermediate Similarity	NPC470037
0.8171	Intermediate Similarity	NPC471969
0.8156	Intermediate Similarity	NPC71610
0.8151	Intermediate Similarity	NPC258502
0.8146	Intermediate Similarity	NPC53520
0.8138	Intermediate Similarity	NPC477139
0.8138	Intermediate Similarity	NPC78307
0.8133	Intermediate Similarity	NPC469447
0.8133	Intermediate Similarity	NPC141817
0.8133	Intermediate Similarity	NPC176030
0.8133	Intermediate Similarity	NPC169214
0.8133	Intermediate Similarity	NPC229218
0.8133	Intermediate Similarity	NPC192597
0.8133	Intermediate Similarity	NPC477873
0.8125	Intermediate Similarity	NPC471851
0.8108	Intermediate Similarity	NPC416
0.8108	Intermediate Similarity	NPC61398
0.8105	Intermediate Similarity	NPC10842
0.8105	Intermediate Similarity	NPC52692
0.8099	Intermediate Similarity	NPC72667
0.8095	Intermediate Similarity	NPC474311
0.8092	Intermediate Similarity	NPC75295
0.8089	Intermediate Similarity	NPC472807
0.8082	Intermediate Similarity	NPC204582
0.8079	Intermediate Similarity	NPC224884
0.8079	Intermediate Similarity	NPC209085
0.8079	Intermediate Similarity	NPC239608
0.8079	Intermediate Similarity	NPC46161
0.8067	Intermediate Similarity	NPC472904
0.8063	Intermediate Similarity	NPC266365
0.8056	Intermediate Similarity	NPC108129
0.8054	Intermediate Similarity	NPC472903
0.8049	Intermediate Similarity	NPC472803
0.8043	Intermediate Similarity	NPC34634
0.8043	Intermediate Similarity	NPC265454
0.8041	Intermediate Similarity	NPC264022
0.8028	Intermediate Similarity	NPC254492
0.8028	Intermediate Similarity	NPC15837
0.8027	Intermediate Similarity	NPC72918
0.8014	Intermediate Similarity	NPC475346
0.8014	Intermediate Similarity	NPC18982
0.8014	Intermediate Similarity	NPC475627
0.8014	Intermediate Similarity	NPC471749
0.8014	Intermediate Similarity	NPC475457
0.8013	Intermediate Similarity	NPC477209
0.8013	Intermediate Similarity	NPC291078
0.8	Intermediate Similarity	NPC474310
0.8	Intermediate Similarity	NPC291001
0.7988	Intermediate Similarity	NPC476017
0.7987	Intermediate Similarity	NPC476821
0.7987	Intermediate Similarity	NPC206207
0.7986	Intermediate Similarity	NPC474546
0.7986	Intermediate Similarity	NPC171460
0.7986	Intermediate Similarity	NPC98305
0.7973	Intermediate Similarity	NPC315275
0.7972	Intermediate Similarity	NPC78364
0.7972	Intermediate Similarity	NPC69424
0.7972	Intermediate Similarity	NPC324209
0.7972	Intermediate Similarity	NPC176130
0.7972	Intermediate Similarity	NPC316553
0.7972	Intermediate Similarity	NPC84672
0.7963	Intermediate Similarity	NPC100420
0.7961	Intermediate Similarity	NPC25491
0.7959	Intermediate Similarity	NPC471913
0.7956	Intermediate Similarity	NPC150919
0.7949	Intermediate Similarity	NPC475311
0.7949	Intermediate Similarity	NPC473680
0.7949	Intermediate Similarity	NPC473579
0.7949	Intermediate Similarity	NPC475454
0.7947	Intermediate Similarity	NPC472410
0.7939	Intermediate Similarity	NPC475058
0.7927	Intermediate Similarity	NPC471975
0.7927	Intermediate Similarity	NPC478060
0.7927	Intermediate Similarity	NPC470374
0.7927	Intermediate Similarity	NPC470377
0.7927	Intermediate Similarity	NPC478059
0.7922	Intermediate Similarity	NPC314437
0.7922	Intermediate Similarity	NPC136878
0.7922	Intermediate Similarity	NPC470330
0.7922	Intermediate Similarity	NPC476535
0.7919	Intermediate Similarity	NPC147418
0.7919	Intermediate Similarity	NPC290030
0.7917	Intermediate Similarity	NPC3009
0.7917	Intermediate Similarity	NPC247250
0.7917	Intermediate Similarity	NPC767
0.7917	Intermediate Similarity	NPC96024
0.7911	Intermediate Similarity	NPC472211
0.7911	Intermediate Similarity	NPC62051
0.7908	Intermediate Similarity	NPC29932
0.7908	Intermediate Similarity	NPC309169
0.7908	Intermediate Similarity	NPC196941
0.7905	Intermediate Similarity	NPC103082
0.7905	Intermediate Similarity	NPC80035
0.7899	Intermediate Similarity	NPC249435
0.7898	Intermediate Similarity	NPC221249
0.7898	Intermediate Similarity	NPC144283
0.7898	Intermediate Similarity	NPC35
0.7895	Intermediate Similarity	NPC469520
0.7891	Intermediate Similarity	NPC327410
0.7891	Intermediate Similarity	NPC53896
0.7891	Intermediate Similarity	NPC52407
0.7887	Intermediate Similarity	NPC234890
0.7887	Intermediate Similarity	NPC199273
0.7887	Intermediate Similarity	NPC74507
0.7887	Intermediate Similarity	NPC15127
0.7885	Intermediate Similarity	NPC327962
0.7885	Intermediate Similarity	NPC44378
0.7885	Intermediate Similarity	NPC280753
0.7881	Intermediate Similarity	NPC203063
0.7881	Intermediate Similarity	NPC304110
0.7881	Intermediate Similarity	NPC27518
0.7881	Intermediate Similarity	NPC82336
0.7881	Intermediate Similarity	NPC78987
0.7872	Intermediate Similarity	NPC139171
0.7872	Intermediate Similarity	NPC91478
0.7867	Intermediate Similarity	NPC182249
0.7867	Intermediate Similarity	NPC87723
0.7867	Intermediate Similarity	NPC13715
0.7867	Intermediate Similarity	NPC141368
0.7862	Intermediate Similarity	NPC314257
0.7862	Intermediate Similarity	NPC303910
0.7862	Intermediate Similarity	NPC262819
0.7862	Intermediate Similarity	NPC117899
0.7862	Intermediate Similarity	NPC276238
0.7857	Intermediate Similarity	NPC73416
0.7857	Intermediate Similarity	NPC236520
0.7857	Intermediate Similarity	NPC66894
0.7857	Intermediate Similarity	NPC476234

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 NPC469854 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	878
0.2-0.3	1504
0.3-0.4	2763
0.4-0.5	2158
0.5-0.6	1117
0.6-0.7	395
0.7-0.8	31
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
0.8188	Intermediate Similarity	NPD8166	Discontinued
0.7742	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD943	Approved
0.766	Intermediate Similarity	NPD2932	Approved
0.7535	Intermediate Similarity	NPD3019	Approved
0.7466	Intermediate Similarity	NPD1470	Approved
0.7389	Intermediate Similarity	NPD3300	Phase 2
0.7386	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6190	Approved
0.7314	Intermediate Similarity	NPD8434	Phase 2
0.731	Intermediate Similarity	NPD1201	Approved
0.7285	Intermediate Similarity	NPD6663	Approved
0.7273	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4628	Phase 3
0.7254	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD9494	Approved
0.7248	Intermediate Similarity	NPD5736	Approved
0.7246	Intermediate Similarity	NPD3022	Approved
0.7246	Intermediate Similarity	NPD3021	Approved
0.7235	Intermediate Similarity	NPD7473	Discontinued
0.7232	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8150	Discontinued
0.7212	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1934	Approved
0.7192	Intermediate Similarity	NPD3092	Approved
0.7159	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3091	Approved
0.7143	Intermediate Similarity	NPD3972	Approved
0.7125	Intermediate Similarity	NPD7390	Discontinued
0.7123	Intermediate Similarity	NPD3026	Approved
0.7123	Intermediate Similarity	NPD3023	Approved
0.7117	Intermediate Similarity	NPD7458	Discontinued
0.7114	Intermediate Similarity	NPD3094	Phase 2
0.7103	Intermediate Similarity	NPD3025	Approved
0.7103	Intermediate Similarity	NPD3024	Approved
0.7095	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3818	Discontinued
0.7078	Intermediate Similarity	NPD230	Phase 1
0.7076	Intermediate Similarity	NPD6166	Phase 2
0.7076	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4380	Phase 2
0.7071	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD3882	Suspended
0.7059	Intermediate Similarity	NPD6232	Discontinued
0.7048	Intermediate Similarity	NPD7819	Suspended
0.7048	Intermediate Similarity	NPD2801	Approved
0.7037	Intermediate Similarity	NPD6273	Approved
0.7029	Intermediate Similarity	NPD7685	Pre-registration
0.7027	Intermediate Similarity	NPD9269	Phase 2
0.7013	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3620	Phase 2
0.7011	Intermediate Similarity	NPD7074	Phase 3
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5034	Approved
0.6989	Remote Similarity	NPD36	Approved
0.6989	Remote Similarity	NPD4955	Approved
0.6989	Remote Similarity	NPD4954	Approved
0.6989	Remote Similarity	NPD5026	Approved
0.6989	Remote Similarity	NPD5028	Approved
0.697	Remote Similarity	NPD7028	Phase 2
0.6964	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7236	Approved
0.6954	Remote Similarity	NPD7054	Approved
0.6949	Remote Similarity	NPD5035	Approved
0.6939	Remote Similarity	NPD3095	Discontinued
0.6932	Remote Similarity	NPD5030	Phase 2
0.6923	Remote Similarity	NPD7075	Discontinued
0.6914	Remote Similarity	NPD1511	Approved
0.6914	Remote Similarity	NPD7472	Approved
0.6909	Remote Similarity	NPD3226	Approved
0.6899	Remote Similarity	NPD2935	Discontinued
0.6883	Remote Similarity	NPD3764	Approved
0.6875	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7266	Discontinued
0.6855	Remote Similarity	NPD2344	Approved
0.6848	Remote Similarity	NPD7239	Suspended
0.6842	Remote Similarity	NPD5494	Approved
0.6836	Remote Similarity	NPD7251	Discontinued
0.6835	Remote Similarity	NPD1510	Phase 2
0.6835	Remote Similarity	NPD2799	Discontinued
0.6833	Remote Similarity	NPD5037	Approved
0.6833	Remote Similarity	NPD5038	Approved
0.6832	Remote Similarity	NPD7003	Approved
0.6829	Remote Similarity	NPD1512	Approved
0.6824	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6651	Approved
0.6809	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3455	Phase 2
0.6798	Remote Similarity	NPD7808	Phase 3
0.678	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6797	Phase 2
0.6778	Remote Similarity	NPD5036	Approved
0.6776	Remote Similarity	NPD1164	Approved
0.6761	Remote Similarity	NPD5844	Phase 1
0.676	Remote Similarity	NPD8313	Approved
0.676	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.676	Remote Similarity	NPD8312	Approved
0.6759	Remote Similarity	NPD2629	Approved
0.6759	Remote Similarity	NPD5951	Approved
0.6757	Remote Similarity	NPD9268	Approved
0.675	Remote Similarity	NPD2346	Discontinued
0.675	Remote Similarity	NPD1471	Phase 3
0.6746	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5761	Phase 2
0.6746	Remote Similarity	NPD5760	Phase 2
0.6742	Remote Similarity	NPD8368	Discontinued
0.6732	Remote Similarity	NPD2798	Approved
0.6728	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4110	Phase 3
0.6726	Remote Similarity	NPD7411	Suspended
0.6725	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4059	Approved
0.6711	Remote Similarity	NPD1876	Approved
0.6709	Remote Similarity	NPD1607	Approved
0.6708	Remote Similarity	NPD1549	Phase 2
0.6706	Remote Similarity	NPD3817	Phase 2
0.6705	Remote Similarity	NPD6959	Discontinued
0.6704	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD9545	Approved
0.6688	Remote Similarity	NPD1240	Approved
0.6687	Remote Similarity	NPD2309	Approved
0.6687	Remote Similarity	NPD6100	Approved
0.6687	Remote Similarity	NPD6099	Approved
0.6686	Remote Similarity	NPD6234	Discontinued
0.6686	Remote Similarity	NPD6801	Discontinued
0.6686	Remote Similarity	NPD37	Approved
0.6686	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5027	Approved
0.6648	Remote Similarity	NPD5029	Approved
0.6648	Remote Similarity	NPD5031	Approved
0.6646	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1755	Approved
0.6643	Remote Similarity	NPD1237	Approved
0.663	Remote Similarity	NPD8407	Phase 2
0.6629	Remote Similarity	NPD4956	Approved
0.6626	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD8032	Phase 2
0.6622	Remote Similarity	NPD7610	Discontinued
0.6622	Remote Similarity	NPD5536	Phase 2
0.662	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD5032	Approved
0.661	Remote Similarity	NPD7799	Discontinued
0.661	Remote Similarity	NPD7228	Approved
0.6607	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD1283	Approved
0.66	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7700	Phase 2
0.6596	Remote Similarity	NPD7699	Phase 2
0.6594	Remote Similarity	NPD3020	Approved
0.6587	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2796	Approved
0.6582	Remote Similarity	NPD826	Approved
0.6582	Remote Similarity	NPD825	Approved
0.6579	Remote Similarity	NPD4878	Approved
0.6576	Remote Similarity	NPD8361	Approved
0.6576	Remote Similarity	NPD8360	Approved
0.657	Remote Similarity	NPD4966	Approved
0.657	Remote Similarity	NPD4967	Phase 2
0.657	Remote Similarity	NPD4965	Approved
0.6566	Remote Similarity	NPD2532	Approved
0.6566	Remote Similarity	NPD2534	Approved
0.6566	Remote Similarity	NPD2533	Approved
0.6564	Remote Similarity	NPD2800	Approved
0.6562	Remote Similarity	NPD8320	Phase 1
0.6562	Remote Similarity	NPD8319	Approved
0.6556	Remote Similarity	NPD6559	Discontinued
0.6556	Remote Similarity	NPD5039	Approved
0.6552	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.655	Remote Similarity	NPD1465	Phase 2
0.6541	Remote Similarity	NPD5735	Approved
0.6533	Remote Similarity	NPD1651	Approved
0.6529	Remote Similarity	NPD6873	Phase 2
0.6524	Remote Similarity	NPD6534	Approved
0.6524	Remote Similarity	NPD6535	Approved
0.6522	Remote Similarity	NPD7742	Approved
0.6522	Remote Similarity	NPD7743	Approved
0.6519	Remote Similarity	NPD7961	Discontinued
0.6516	Remote Similarity	NPD257	Approved
0.6516	Remote Similarity	NPD258	Approved
0.6513	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5350	Clinical (unspecified phase)

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