NPASS Compound

Structure

NPC206207 OpenBabel07101718192D 26 27 0 0 0 0 0 0 0 0999 V2000 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 6 1 0 0 0 0 4 12 2 0 0 0 0 5 8 1 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 19 2 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 11 22 2 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 17 1 0 0 0 0 14 20 2 0 0 0 0 15 19 1 0 0 0 0 16 23 1 0 0 0 0 18 21 2 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	377.519
LogP:	4.401
LogD:	2.955
LogS:	-3.788
# Rotatable Bonds:	6
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	2.992
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.934
MDCK Permeability:	7.877390089561231e-06
Pgp-inhibitor:	0.017
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.885
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	99.8883285522461%
Volume Distribution (VD):	0.363
Pgp-substrate:	1.3758172988891602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.877
CYP1A2-substrate:	0.641
CYP2C19-inhibitor:	0.512
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.595
CYP2C9-substrate:	0.85
CYP2D6-inhibitor:	0.843
CYP2D6-substrate:	0.714
CYP3A4-inhibitor:	0.294
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	8.723
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.055
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.356
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.945
Carcinogencity:	0.066
Eye Corrosion:	0.053
Eye Irritation:	0.94
Respiratory Toxicity:	0.237

Download Data

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

Natural Product: NPC206207

Natural Product ID:	NPC206207
*Common Name:**	Panicein C
IUPAC Name:	5-[(E)-5-(2,5-dihydroxyphenyl)-3-methylpent-3-enyl]-2,3-dihydroxy-4,6-dimethylbenzaldehyde
Synonyms:	Panicein C
Standard InCHIKey:	KTKUNEUPWDRROX-UUILKARUSA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-12(4-6-15-10-16(23)7-9-19(15)24)5-8-17-13(2)18(11-22)21(26)20(25)14(17)3/h4,7,9-11,23-26H,5-6,8H2,1-3H3/b12-4+
SMILES:	O=Cc1c(C)c(CC/C(=C/Cc2cc(O)ccc2O)/C)c(c(c1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483627
PubChem CID:	5467408
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32520	reniera fulva	Species	n.a.	n.a.	n.a.	Mediterranean	n.a.	PMID[8388433]

☑ 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
GI50	55
Others	3

Activity Type	# Activity
Cell Line	58

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	=	3311.31	nM	PMID[477620]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	TGI	=	9549.93	nM	PMID[477620]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	=	5248.07	nM	PMID[477620]
NPT455	Cell Line	NCI-H522	Homo sapiens	TGI	=	21379.62	nM	PMID[477620]
NPT455	Cell Line	NCI-H522	Homo sapiens	LC50	=	63095.73	nM	PMID[477620]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	26668.59	nM	PMID[477621]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	18365.38	nM	PMID[477621]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	20323.57	nM	PMID[477621]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	28183.83	nM	PMID[477621]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	15667.51	nM	PMID[477621]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[477621]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	18407.72	nM	PMID[477621]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	15523.87	nM	PMID[477621]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	32885.16	nM	PMID[477621]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[477621]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	21232.44	nM	PMID[477621]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	49203.95	nM	PMID[477621]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	17100.15	nM	PMID[477621]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	18578.04	nM	PMID[477621]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	17947.34	nM	PMID[477621]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	35237.09	nM	PMID[477621]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	27478.94	nM	PMID[477621]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	7379.04	nM	PMID[477621]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	48194.78	nM	PMID[477621]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	35645.11	nM	PMID[477621]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	17701.09	nM	PMID[477621]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	5236.0	nM	PMID[477621]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	25527.01	nM	PMID[477621]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	20323.57	nM	PMID[477621]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	19952.62	nM	PMID[477621]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	35563.13	nM	PMID[477621]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	17418.07	nM	PMID[477621]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	26485.0	nM	PMID[477621]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	23173.95	nM	PMID[477621]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	30408.85	nM	PMID[477621]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	37497.3	nM	PMID[477621]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	33265.96	nM	PMID[477621]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	47863.01	nM	PMID[477621]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	31405.09	nM	PMID[477621]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	19142.56	nM	PMID[477621]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	26977.39	nM	PMID[477621]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	36057.86	nM	PMID[477621]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	9638.29	nM	PMID[477621]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	17988.71	nM	PMID[477621]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	26730.06	nM	PMID[477621]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	23768.4	nM	PMID[477621]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	26668.59	nM	PMID[477621]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	17060.82	nM	PMID[477621]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	25409.73	nM	PMID[477621]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	25644.84	nM	PMID[477621]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	3280.95	nM	PMID[477621]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	21134.89	nM	PMID[477621]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	34514.37	nM	PMID[477621]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	29241.52	nM	PMID[477621]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	18113.4	nM	PMID[477621]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	18578.04	nM	PMID[477621]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	16143.59	nM	PMID[477621]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	18749.95	nM	PMID[477621]

☑ 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 NPC206207 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	333
0.1-0.2	1517
0.2-0.3	3576
0.3-0.4	10698
0.4-0.5	8519
0.5-0.6	4825
0.6-0.7	8885
0.7-0.8	4095
0.8-0.85	213
0.85-0.9	29
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9466	High Similarity	NPC85342
0.9407	High Similarity	NPC141368
0.9084	High Similarity	NPC136342
0.9084	High Similarity	NPC295202
0.9084	High Similarity	NPC227741
0.9084	High Similarity	NPC49647
0.9008	High Similarity	NPC131799
0.8944	High Similarity	NPC68441
0.8929	High Similarity	NPC187843
0.8881	High Similarity	NPC476535
0.8803	High Similarity	NPC199936
0.8768	High Similarity	NPC258502
0.8741	High Similarity	NPC474546
0.8714	High Similarity	NPC61398
0.8714	High Similarity	NPC416
0.8707	High Similarity	NPC75377
0.8649	High Similarity	NPC3744
0.8643	High Similarity	NPC147418
0.8639	High Similarity	NPC476532
0.8639	High Similarity	NPC474191
0.8623	High Similarity	NPC294226
0.8613	High Similarity	NPC41847
0.8593	High Similarity	NPC473787
0.8581	High Similarity	NPC70320
0.854	High Similarity	NPC117609
0.8529	High Similarity	NPC48248
0.8523	High Similarity	NPC476533
0.8523	High Similarity	NPC137125
0.8519	High Similarity	NPC306765
0.8511	High Similarity	NPC305060
0.8507	High Similarity	NPC68756
0.8507	High Similarity	NPC152525
0.85	High Similarity	NPC153088
0.8493	Intermediate Similarity	NPC39361
0.8489	Intermediate Similarity	NPC52407
0.8489	Intermediate Similarity	NPC314048
0.8478	Intermediate Similarity	NPC205992
0.8478	Intermediate Similarity	NPC291001
0.8462	Intermediate Similarity	NPC471853
0.8462	Intermediate Similarity	NPC476534
0.8456	Intermediate Similarity	NPC471530
0.8451	Intermediate Similarity	NPC123714
0.844	Intermediate Similarity	NPC272268
0.8417	Intermediate Similarity	NPC110609
0.8417	Intermediate Similarity	NPC242358
0.8417	Intermediate Similarity	NPC246693
0.8414	Intermediate Similarity	NPC238629
0.8406	Intermediate Similarity	NPC31539
0.8406	Intermediate Similarity	NPC199253
0.8406	Intermediate Similarity	NPC136588
0.84	Intermediate Similarity	NPC164912
0.8394	Intermediate Similarity	NPC3009
0.8382	Intermediate Similarity	NPC96915
0.838	Intermediate Similarity	NPC290030
0.838	Intermediate Similarity	NPC245923
0.8378	Intermediate Similarity	NPC55327
0.837	Intermediate Similarity	NPC234890
0.837	Intermediate Similarity	NPC74507
0.8369	Intermediate Similarity	NPC283088
0.8357	Intermediate Similarity	NPC53896
0.8357	Intermediate Similarity	NPC138472
0.8357	Intermediate Similarity	NPC111845
0.8356	Intermediate Similarity	NPC300603
0.8356	Intermediate Similarity	NPC91694
0.8345	Intermediate Similarity	NPC244699
0.8345	Intermediate Similarity	NPC329493
0.8344	Intermediate Similarity	NPC474000
0.8333	Intermediate Similarity	NPC118427
0.8333	Intermediate Similarity	NPC144283
0.8333	Intermediate Similarity	NPC99731
0.8333	Intermediate Similarity	NPC34414
0.8333	Intermediate Similarity	NPC146647
0.831	Intermediate Similarity	NPC65005
0.831	Intermediate Similarity	NPC474813
0.831	Intermediate Similarity	NPC194764
0.831	Intermediate Similarity	NPC264112
0.831	Intermediate Similarity	NPC155211
0.8298	Intermediate Similarity	NPC50924
0.8286	Intermediate Similarity	NPC70622
0.8276	Intermediate Similarity	NPC472904
0.8273	Intermediate Similarity	NPC244441
0.8273	Intermediate Similarity	NPC55949
0.8269	Intermediate Similarity	NPC101769
0.8267	Intermediate Similarity	NPC470037
0.8264	Intermediate Similarity	NPC472903
0.8261	Intermediate Similarity	NPC234175
0.8261	Intermediate Similarity	NPC767
0.8261	Intermediate Similarity	NPC247250
0.8261	Intermediate Similarity	NPC282923
0.8258	Intermediate Similarity	NPC184527
0.8243	Intermediate Similarity	NPC63918
0.8239	Intermediate Similarity	NPC72918
0.8235	Intermediate Similarity	NPC173978
0.8235	Intermediate Similarity	NPC142956
0.8235	Intermediate Similarity	NPC279605
0.8231	Intermediate Similarity	NPC10764
0.8231	Intermediate Similarity	NPC244691
0.8231	Intermediate Similarity	NPC79627
0.8227	Intermediate Similarity	NPC115458
0.8224	Intermediate Similarity	NPC475770
0.8222	Intermediate Similarity	NPC307174
0.8222	Intermediate Similarity	NPC86900
0.8219	Intermediate Similarity	NPC11314
0.8219	Intermediate Similarity	NPC248068
0.8219	Intermediate Similarity	NPC474961
0.8214	Intermediate Similarity	NPC474517
0.8214	Intermediate Similarity	NPC72669
0.8212	Intermediate Similarity	NPC473201
0.8212	Intermediate Similarity	NPC302783
0.8209	Intermediate Similarity	NPC98305
0.8207	Intermediate Similarity	NPC203063
0.8201	Intermediate Similarity	NPC278928
0.8194	Intermediate Similarity	NPC230811
0.8194	Intermediate Similarity	NPC141574
0.8182	Intermediate Similarity	NPC86524
0.8182	Intermediate Similarity	NPC118919
0.8182	Intermediate Similarity	NPC28169
0.8182	Intermediate Similarity	NPC7464
0.8182	Intermediate Similarity	NPC472308
0.8176	Intermediate Similarity	NPC73416
0.8176	Intermediate Similarity	NPC160777
0.8169	Intermediate Similarity	NPC282780
0.8169	Intermediate Similarity	NPC166480
0.8169	Intermediate Similarity	NPC202225
0.8162	Intermediate Similarity	NPC275145
0.8162	Intermediate Similarity	NPC375356
0.8156	Intermediate Similarity	NPC58685
0.8153	Intermediate Similarity	NPC477689
0.8151	Intermediate Similarity	NPC124365
0.8151	Intermediate Similarity	NPC92079
0.8148	Intermediate Similarity	NPC295034
0.8146	Intermediate Similarity	NPC280295
0.8143	Intermediate Similarity	NPC31799
0.8143	Intermediate Similarity	NPC62219
0.8141	Intermediate Similarity	NPC311740
0.8138	Intermediate Similarity	NPC138099
0.8138	Intermediate Similarity	NPC162939
0.8138	Intermediate Similarity	NPC143438
0.8138	Intermediate Similarity	NPC242994
0.8134	Intermediate Similarity	NPC7151
0.8134	Intermediate Similarity	NPC34634
0.8134	Intermediate Similarity	NPC473662
0.8134	Intermediate Similarity	NPC216297
0.8134	Intermediate Similarity	NPC265454
0.8129	Intermediate Similarity	NPC96024
0.8125	Intermediate Similarity	NPC49911
0.8125	Intermediate Similarity	NPC264022
0.8125	Intermediate Similarity	NPC62907
0.8125	Intermediate Similarity	NPC277559
0.8121	Intermediate Similarity	NPC285122
0.8117	Intermediate Similarity	NPC213401
0.8116	Intermediate Similarity	NPC160499
0.8116	Intermediate Similarity	NPC472047
0.8112	Intermediate Similarity	NPC22222
0.8112	Intermediate Similarity	NPC281513
0.8112	Intermediate Similarity	NPC80035
0.8108	Intermediate Similarity	NPC275278
0.8108	Intermediate Similarity	NPC29932
0.8106	Intermediate Similarity	NPC477453
0.8105	Intermediate Similarity	NPC93552
0.8102	Intermediate Similarity	NPC199273
0.8101	Intermediate Similarity	NPC26386
0.8099	Intermediate Similarity	NPC225051
0.8099	Intermediate Similarity	NPC477139
0.8095	Intermediate Similarity	NPC474300
0.8095	Intermediate Similarity	NPC73061
0.8095	Intermediate Similarity	NPC469855
0.8095	Intermediate Similarity	NPC314271
0.8095	Intermediate Similarity	NPC471972
0.8095	Intermediate Similarity	NPC135524
0.8095	Intermediate Similarity	NPC471971
0.8095	Intermediate Similarity	NPC30846
0.8092	Intermediate Similarity	NPC35
0.8088	Intermediate Similarity	NPC300274
0.8088	Intermediate Similarity	NPC11250
0.8088	Intermediate Similarity	NPC283514
0.8085	Intermediate Similarity	NPC471851
0.8085	Intermediate Similarity	NPC93015
0.8082	Intermediate Similarity	NPC82336
0.8082	Intermediate Similarity	NPC181560
0.8082	Intermediate Similarity	NPC183345
0.8082	Intermediate Similarity	NPC169452
0.8082	Intermediate Similarity	NPC78987
0.8077	Intermediate Similarity	NPC119224
0.8077	Intermediate Similarity	NPC84571
0.8074	Intermediate Similarity	NPC472046
0.8074	Intermediate Similarity	NPC216216
0.8071	Intermediate Similarity	NPC276238
0.8069	Intermediate Similarity	NPC4214
0.8069	Intermediate Similarity	NPC13715
0.8069	Intermediate Similarity	NPC473479
0.8069	Intermediate Similarity	NPC157284
0.8069	Intermediate Similarity	NPC149773
0.8069	Intermediate Similarity	NPC114333
0.8069	Intermediate Similarity	NPC28592
0.8069	Intermediate Similarity	NPC245760
0.8069	Intermediate Similarity	NPC297797
0.8069	Intermediate Similarity	NPC51531
0.8069	Intermediate Similarity	NPC473779
0.8069	Intermediate Similarity	NPC165191

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 NPC206207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	952
0.2-0.3	1456
0.3-0.4	2848
0.4-0.5	1963
0.5-0.6	1142
0.6-0.7	428
0.7-0.8	48
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8944	High Similarity	NPD7422	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD1470	Approved
0.8028	Intermediate Similarity	NPD943	Approved
0.8015	Intermediate Similarity	NPD1201	Approved
0.8	Intermediate Similarity	NPD2935	Discontinued
0.7931	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD5404	Approved
0.7877	Intermediate Similarity	NPD5406	Approved
0.7877	Intermediate Similarity	NPD5408	Approved
0.7877	Intermediate Similarity	NPD5405	Approved
0.7808	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6232	Discontinued
0.7748	Intermediate Similarity	NPD7390	Discontinued
0.7704	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD3300	Phase 2
0.7643	Intermediate Similarity	NPD2801	Approved
0.7607	Intermediate Similarity	NPD7473	Discontinued
0.7588	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2346	Discontinued
0.7576	Intermediate Similarity	NPD3021	Approved
0.7576	Intermediate Similarity	NPD3022	Approved
0.7537	Intermediate Similarity	NPD7635	Approved
0.7535	Intermediate Similarity	NPD1164	Approved
0.7468	Intermediate Similarity	NPD1934	Approved
0.7434	Intermediate Similarity	NPD8166	Discontinued
0.7431	Intermediate Similarity	NPD9494	Approved
0.7357	Intermediate Similarity	NPD3019	Approved
0.7357	Intermediate Similarity	NPD2932	Approved
0.7355	Intermediate Similarity	NPD2533	Approved
0.7355	Intermediate Similarity	NPD2534	Approved
0.7355	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD2799	Discontinued
0.7329	Intermediate Similarity	NPD3882	Suspended
0.7305	Intermediate Similarity	NPD5844	Phase 1
0.729	Intermediate Similarity	NPD1511	Approved
0.7278	Intermediate Similarity	NPD3226	Approved
0.7222	Intermediate Similarity	NPD1283	Approved
0.7208	Intermediate Similarity	NPD7003	Approved
0.7197	Intermediate Similarity	NPD1512	Approved
0.7195	Intermediate Similarity	NPD5494	Approved
0.7163	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1651	Approved
0.7153	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6959	Discontinued
0.7134	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD230	Phase 1
0.7126	Intermediate Similarity	NPD6166	Phase 2
0.7126	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4380	Phase 2
0.7113	Intermediate Similarity	NPD4626	Approved
0.7099	Intermediate Similarity	NPD7819	Suspended
0.7086	Intermediate Similarity	NPD1607	Approved
0.7083	Intermediate Similarity	NPD9269	Phase 2
0.7076	Intermediate Similarity	NPD6559	Discontinued
0.7069	Intermediate Similarity	NPD8150	Discontinued
0.7067	Intermediate Similarity	NPD2979	Phase 3
0.7067	Intermediate Similarity	NPD4060	Phase 1
0.7051	Intermediate Similarity	NPD6190	Approved
0.705	Intermediate Similarity	NPD5951	Approved
0.7047	Intermediate Similarity	NPD2313	Discontinued
0.7047	Intermediate Similarity	NPD3764	Approved
0.7041	Intermediate Similarity	NPD3818	Discontinued
0.7037	Intermediate Similarity	NPD2342	Discontinued
0.702	Intermediate Similarity	NPD447	Suspended
0.7014	Intermediate Similarity	NPD1281	Approved
0.7013	Intermediate Similarity	NPD2344	Approved
0.7012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2798	Approved
0.7006	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6663	Approved
0.6993	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1510	Phase 2
0.6987	Remote Similarity	NPD4628	Phase 3
0.6968	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7074	Phase 3
0.6959	Remote Similarity	NPD5736	Approved
0.6957	Remote Similarity	NPD7458	Discontinued
0.6957	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3455	Phase 2
0.6954	Remote Similarity	NPD1240	Approved
0.6951	Remote Similarity	NPD3817	Phase 2
0.695	Remote Similarity	NPD9493	Approved
0.6948	Remote Similarity	NPD1551	Phase 2
0.6946	Remote Similarity	NPD1247	Approved
0.6944	Remote Similarity	NPD3026	Approved
0.6944	Remote Similarity	NPD3023	Approved
0.6939	Remote Similarity	NPD3094	Phase 2
0.6936	Remote Similarity	NPD5028	Approved
0.6936	Remote Similarity	NPD5034	Approved
0.6936	Remote Similarity	NPD4955	Approved
0.6936	Remote Similarity	NPD36	Approved
0.6936	Remote Similarity	NPD5026	Approved
0.6936	Remote Similarity	NPD4954	Approved
0.6936	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD497	Approved
0.6928	Remote Similarity	NPD6234	Discontinued
0.6923	Remote Similarity	NPD3025	Approved
0.6923	Remote Similarity	NPD5691	Approved
0.6923	Remote Similarity	NPD3024	Approved
0.6918	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7054	Approved
0.6897	Remote Similarity	NPD8313	Approved
0.6897	Remote Similarity	NPD8312	Approved
0.6897	Remote Similarity	NPD3092	Approved
0.6894	Remote Similarity	NPD3020	Approved
0.6884	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5030	Phase 2
0.6867	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7075	Discontinued
0.6861	Remote Similarity	NPD9266	Approved
0.6861	Remote Similarity	NPD74	Approved
0.686	Remote Similarity	NPD7472	Approved
0.6857	Remote Similarity	NPD495	Approved
0.6857	Remote Similarity	NPD498	Approved
0.6857	Remote Similarity	NPD496	Approved
0.6853	Remote Similarity	NPD3091	Approved
0.6849	Remote Similarity	NPD3972	Approved
0.6848	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD826	Approved
0.6842	Remote Similarity	NPD825	Approved
0.6839	Remote Similarity	NPD2438	Suspended
0.6835	Remote Similarity	NPD2309	Approved
0.6833	Remote Similarity	NPD6535	Approved
0.6833	Remote Similarity	NPD6534	Approved
0.6829	Remote Similarity	NPD37	Approved
0.6821	Remote Similarity	NPD6797	Phase 2
0.6815	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6599	Discontinued
0.6807	Remote Similarity	NPD7768	Phase 2
0.6806	Remote Similarity	NPD9268	Approved
0.6805	Remote Similarity	NPD5711	Approved
0.6805	Remote Similarity	NPD5710	Approved
0.6795	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD2859	Approved
0.6794	Remote Similarity	NPD2860	Approved
0.6794	Remote Similarity	NPD844	Approved
0.6788	Remote Similarity	NPD9267	Approved
0.6788	Remote Similarity	NPD9264	Approved
0.6788	Remote Similarity	NPD1465	Phase 2
0.6788	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD9263	Approved
0.6782	Remote Similarity	NPD5027	Approved
0.6782	Remote Similarity	NPD7251	Discontinued
0.6782	Remote Similarity	NPD5029	Approved
0.6782	Remote Similarity	NPD5031	Approved
0.678	Remote Similarity	NPD5037	Approved
0.678	Remote Similarity	NPD5038	Approved
0.6779	Remote Similarity	NPD257	Approved
0.6779	Remote Similarity	NPD258	Approved
0.6778	Remote Similarity	NPD6212	Phase 3
0.6778	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6213	Phase 3
0.6772	Remote Similarity	NPD3400	Discontinued
0.677	Remote Similarity	NPD6273	Approved
0.6759	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1876	Approved
0.6755	Remote Similarity	NPD3027	Phase 3
0.6752	Remote Similarity	NPD1549	Phase 2
0.6747	Remote Similarity	NPD5402	Approved
0.6742	Remote Similarity	NPD288	Approved
0.6739	Remote Similarity	NPD6776	Approved
0.6739	Remote Similarity	NPD6777	Approved
0.6739	Remote Similarity	NPD6778	Approved
0.6739	Remote Similarity	NPD6780	Approved
0.6739	Remote Similarity	NPD6779	Approved
0.6739	Remote Similarity	NPD6781	Approved
0.6739	Remote Similarity	NPD6782	Approved
0.6738	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3620	Phase 2
0.6731	Remote Similarity	NPD4477	Approved
0.6731	Remote Similarity	NPD2531	Phase 2
0.6731	Remote Similarity	NPD4476	Approved
0.6727	Remote Similarity	NPD6844	Discontinued
0.6723	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5036	Approved
0.6722	Remote Similarity	NPD5968	Phase 3
0.6721	Remote Similarity	NPD7700	Phase 2
0.6721	Remote Similarity	NPD7699	Phase 2
0.6718	Remote Similarity	NPD2933	Approved
0.6718	Remote Similarity	NPD2934	Approved
0.6711	Remote Similarity	NPD1203	Approved
0.6708	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4965	Approved
0.6707	Remote Similarity	NPD4967	Phase 2
0.6707	Remote Similarity	NPD4966	Approved
0.6689	Remote Similarity	NPD6832	Phase 2
0.6688	Remote Similarity	NPD1471	Phase 3
0.6688	Remote Similarity	NPD7266	Discontinued
0.6688	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD1547	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