NPASS Compound

Structure

CID309190 OpenBabel06191716112D 29 31 0 0 1 0 0 0 0 0999 V2000 -1.6953 2.1395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6275 2.7681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4500 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6797 1.5431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2748 1.4466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2785 1.6275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5601 1.0712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7446 -1.2825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9295 0.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4181 -1.4228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0702 0.5813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7427 -0.1115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2529 1.0712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6238 2.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8670 -0.2240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7427 0.5813 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3597 -0.2860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9653 3.3661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1307 0.5634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9642 0.8162 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2529 -0.6013 0.0000 C 0 0 2 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 0.6231 -0.7564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8110 1.0238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3105 4.3258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9615 3.1852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9986 1.0992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5279 0.2534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1442 1.1943 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 5 6 1 0 0 0 0 5 9 2 0 0 0 0 6 14 2 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 14 18 1 0 0 0 0 15 23 2 0 0 0 0 15 28 1 0 0 0 0 16 24 1 1 0 0 0 17 20 1 6 0 0 0 17 22 1 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 19 21 1 0 0 0 0 19 27 2 0 0 0 0 19 29 1 0 0 0 0 20 4 1 1 0 0 0 20 29 1 0 0 0 0 21 22 1 1 0 0 0 22 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.18
Volume:	409.112
LogP:	1.305
LogD:	0.07
LogS:	-3.11
# Rotatable Bonds:	5
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.321
Synthetic Accessibility Score:	5.647
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.508
MDCK Permeability:	1.1560404345800634e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.763
20% Bioavailability (F20%):	0.294
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	57.59344482421875%
Volume Distribution (VD):	0.287
Pgp-substrate:	25.4555606842041%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.368
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.207
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.812
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.299
CYP3A4-substrate:	0.235

ADMET: Excretion

Clearance (CL):	2.25
Half-life (T1/2):	0.486

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.728
Drug-inuced Liver Injury (DILI):	0.771
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.953
Maximum Recommended Daily Dose:	0.366
Skin Sensitization:	0.193
Carcinogencity:	0.834
Eye Corrosion:	0.005
Eye Irritation:	0.063
Respiratory Toxicity:	0.744

Download Data

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

Natural Product: NPC309190

Natural Product ID:	NPC309190
*Common Name:**	Pseudolaric Acid G
IUPAC Name:	n.a.
Synonyms:	Pseudolaric Acid G
Standard InCHIKey:	GFNSUMXEBWZIRI-OXLLHMEESA-N
Standard InCHI:	InChI=1S/C22H28O7/c1-13-7-11-22(28-15(3)23)17-8-10-21(22,12-16(13)24)19(27)29-20(17,4)9-5-6-14(2)18(25)26/h5-7,9,16-17,24H,8,10-12H2,1-4H3,(H,25,26)/b9-5+,14-6+/t16-,17+,20-,21+,22+/m1/s1
SMILES:	CC(=O)O[C@@]12CC=C([C@@H](C[C@@]32CC[C@H]1[C@@](C)(/C=C/C=C(/C(=O)O)C)OC3=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL222475
PubChem CID:	10894737
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene 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
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346966]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root bark	n.a.	n.a.	PMID[14527554]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	tuber	n.a.	PMID[15180301]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	leaves,?stems	USA	n.a.	PMID[16124770]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17291040]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17381154]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root and trunk bark	n.a.	n.a.	PMID[18078313]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078313]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23668986]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25843525]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760078]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377017]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5178	Pelophylax nigromaculatus	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20772	Pedalium murex	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5178	Pelophylax nigromaculatus	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20262	Delia paludosa	Species	Anthomyiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22563	Sclerocarya birrea	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21914	Turnera angustifolia	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20328	Plumeria acutifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22700	Dacrydium comosum	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21090	Chrysanthemum ornatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	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	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	10970.0	nM	PMID[494909]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[494910]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[494909]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[494910]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[494910]

☑ 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 NPC309190 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	189
0.1-0.2	980
0.2-0.3	3716
0.3-0.4	7787
0.4-0.5	13842
0.5-0.6	8357
0.6-0.7	5752
0.7-0.8	2000
0.8-0.85	57
0.85-0.9	10
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9479	High Similarity	NPC64742
0.9286	High Similarity	NPC206079
0.9271	High Similarity	NPC9812
0.9091	High Similarity	NPC116139
0.9082	High Similarity	NPC244411
0.9	High Similarity	NPC66110
0.89	High Similarity	NPC62670
0.88	High Similarity	NPC280963
0.8649	High Similarity	NPC470829
0.8649	High Similarity	NPC473228
0.86	High Similarity	NPC47834
0.8529	High Similarity	NPC477950
0.8515	High Similarity	NPC141191
0.8431	Intermediate Similarity	NPC469872
0.8431	Intermediate Similarity	NPC469864
0.8416	Intermediate Similarity	NPC169205
0.8378	Intermediate Similarity	NPC13710
0.8367	Intermediate Similarity	NPC77337
0.8318	Intermediate Similarity	NPC47951
0.8317	Intermediate Similarity	NPC185553
0.8265	Intermediate Similarity	NPC212664
0.8265	Intermediate Similarity	NPC212598
0.8257	Intermediate Similarity	NPC138757
0.8257	Intermediate Similarity	NPC76550
0.8257	Intermediate Similarity	NPC123855
0.8218	Intermediate Similarity	NPC48803
0.8218	Intermediate Similarity	NPC90121
0.8218	Intermediate Similarity	NPC193645
0.8218	Intermediate Similarity	NPC275960
0.8218	Intermediate Similarity	NPC469873
0.819	Intermediate Similarity	NPC183570
0.8182	Intermediate Similarity	NPC106395
0.8182	Intermediate Similarity	NPC46269
0.8173	Intermediate Similarity	NPC244456
0.8173	Intermediate Similarity	NPC469657
0.8173	Intermediate Similarity	NPC171759
0.8119	Intermediate Similarity	NPC167219
0.8113	Intermediate Similarity	NPC100487
0.8108	Intermediate Similarity	NPC138303
0.8108	Intermediate Similarity	NPC67290
0.8108	Intermediate Similarity	NPC133677
0.81	Intermediate Similarity	NPC111114
0.81	Intermediate Similarity	NPC472705
0.81	Intermediate Similarity	NPC300312
0.81	Intermediate Similarity	NPC261607
0.8095	Intermediate Similarity	NPC118405
0.8058	Intermediate Similarity	NPC213947
0.8058	Intermediate Similarity	NPC202705
0.8058	Intermediate Similarity	NPC108475
0.8058	Intermediate Similarity	NPC161493
0.8058	Intermediate Similarity	NPC477949
0.8058	Intermediate Similarity	NPC170143
0.8056	Intermediate Similarity	NPC220155
0.8039	Intermediate Similarity	NPC52044
0.8039	Intermediate Similarity	NPC67584
0.802	Intermediate Similarity	NPC476049
0.8019	Intermediate Similarity	NPC280566
0.8	Intermediate Similarity	NPC474315
0.8	Intermediate Similarity	NPC129419
0.8	Intermediate Similarity	NPC150923
0.7981	Intermediate Similarity	NPC222011
0.7965	Intermediate Similarity	NPC476959
0.7963	Intermediate Similarity	NPC91034
0.7963	Intermediate Similarity	NPC476958
0.7961	Intermediate Similarity	NPC213078
0.7959	Intermediate Similarity	NPC116575
0.7944	Intermediate Similarity	NPC203659
0.7944	Intermediate Similarity	NPC272632
0.7941	Intermediate Similarity	NPC96541
0.7941	Intermediate Similarity	NPC53685
0.7928	Intermediate Similarity	NPC475970
0.7921	Intermediate Similarity	NPC123177
0.7921	Intermediate Similarity	NPC70595
0.7921	Intermediate Similarity	NPC284185
0.7921	Intermediate Similarity	NPC150978
0.7921	Intermediate Similarity	NPC74103
0.7913	Intermediate Similarity	NPC476962
0.7909	Intermediate Similarity	NPC257240
0.7905	Intermediate Similarity	NPC227865
0.7905	Intermediate Similarity	NPC290802
0.79	Intermediate Similarity	NPC115179
0.79	Intermediate Similarity	NPC12872
0.79	Intermediate Similarity	NPC106040
0.79	Intermediate Similarity	NPC268298
0.79	Intermediate Similarity	NPC168679
0.7885	Intermediate Similarity	NPC40812
0.7885	Intermediate Similarity	NPC69385
0.787	Intermediate Similarity	NPC243998
0.7864	Intermediate Similarity	NPC37408
0.7864	Intermediate Similarity	NPC272050
0.7864	Intermediate Similarity	NPC209355
0.7864	Intermediate Similarity	NPC170120
0.7864	Intermediate Similarity	NPC304886
0.7864	Intermediate Similarity	NPC213698
0.7857	Intermediate Similarity	NPC165162
0.785	Intermediate Similarity	NPC475945
0.785	Intermediate Similarity	NPC110989
0.785	Intermediate Similarity	NPC475871
0.783	Intermediate Similarity	NPC146822
0.783	Intermediate Similarity	NPC476223
0.783	Intermediate Similarity	NPC224720
0.783	Intermediate Similarity	NPC475099
0.783	Intermediate Similarity	NPC476240
0.7822	Intermediate Similarity	NPC145666
0.7822	Intermediate Similarity	NPC469368
0.7822	Intermediate Similarity	NPC253144
0.7818	Intermediate Similarity	NPC228477
0.7818	Intermediate Similarity	NPC137911
0.781	Intermediate Similarity	NPC316598
0.781	Intermediate Similarity	NPC308567
0.781	Intermediate Similarity	NPC187761
0.781	Intermediate Similarity	NPC221615
0.781	Intermediate Similarity	NPC261377
0.781	Intermediate Similarity	NPC83895
0.781	Intermediate Similarity	NPC255592
0.7807	Intermediate Similarity	NPC239273
0.78	Intermediate Similarity	NPC476805
0.7788	Intermediate Similarity	NPC305044
0.7788	Intermediate Similarity	NPC265290
0.7788	Intermediate Similarity	NPC24956
0.7788	Intermediate Similarity	NPC142529
0.7788	Intermediate Similarity	NPC91771
0.7788	Intermediate Similarity	NPC18019
0.7788	Intermediate Similarity	NPC126156
0.7778	Intermediate Similarity	NPC234038
0.7778	Intermediate Similarity	NPC121099
0.7778	Intermediate Similarity	NPC475461
0.7778	Intermediate Similarity	NPC239162
0.7778	Intermediate Similarity	NPC305475
0.7768	Intermediate Similarity	NPC100267
0.7768	Intermediate Similarity	NPC191620
0.7768	Intermediate Similarity	NPC221144
0.7768	Intermediate Similarity	NPC475524
0.7767	Intermediate Similarity	NPC127019
0.7767	Intermediate Similarity	NPC477131
0.7767	Intermediate Similarity	NPC65829
0.7757	Intermediate Similarity	NPC225353
0.7757	Intermediate Similarity	NPC478156
0.7757	Intermediate Similarity	NPC235369
0.7757	Intermediate Similarity	NPC474747
0.7755	Intermediate Similarity	NPC196487
0.7755	Intermediate Similarity	NPC156485
0.7755	Intermediate Similarity	NPC14575
0.7748	Intermediate Similarity	NPC41551
0.7748	Intermediate Similarity	NPC37116
0.7748	Intermediate Similarity	NPC477103
0.7745	Intermediate Similarity	NPC45579
0.7745	Intermediate Similarity	NPC221282
0.7745	Intermediate Similarity	NPC177037
0.7745	Intermediate Similarity	NPC472814
0.7736	Intermediate Similarity	NPC477521
0.7736	Intermediate Similarity	NPC288876
0.7736	Intermediate Similarity	NPC476274
0.7736	Intermediate Similarity	NPC475053
0.7732	Intermediate Similarity	NPC89555
0.7723	Intermediate Similarity	NPC117405
0.7723	Intermediate Similarity	NPC52198
0.7719	Intermediate Similarity	NPC148458
0.7714	Intermediate Similarity	NPC87090
0.7714	Intermediate Similarity	NPC474343
0.7706	Intermediate Similarity	NPC314244
0.7706	Intermediate Similarity	NPC223450
0.7706	Intermediate Similarity	NPC179891
0.77	Intermediate Similarity	NPC201658
0.77	Intermediate Similarity	NPC86005
0.77	Intermediate Similarity	NPC237540
0.7699	Intermediate Similarity	NPC469496
0.7699	Intermediate Similarity	NPC122056
0.7699	Intermediate Similarity	NPC9848
0.7699	Intermediate Similarity	NPC469454
0.7699	Intermediate Similarity	NPC209058
0.7699	Intermediate Similarity	NPC469463
0.7699	Intermediate Similarity	NPC312017
0.7692	Intermediate Similarity	NPC46570
0.7692	Intermediate Similarity	NPC20546
0.7685	Intermediate Similarity	NPC72151
0.7685	Intermediate Similarity	NPC472755
0.7685	Intermediate Similarity	NPC473283
0.7685	Intermediate Similarity	NPC329345
0.7685	Intermediate Similarity	NPC168575
0.7685	Intermediate Similarity	NPC475526
0.7679	Intermediate Similarity	NPC179798
0.7679	Intermediate Similarity	NPC287311
0.7679	Intermediate Similarity	NPC304180
0.7677	Intermediate Similarity	NPC255307
0.7677	Intermediate Similarity	NPC474369
0.7677	Intermediate Similarity	NPC470755
0.7677	Intermediate Similarity	NPC245434
0.7677	Intermediate Similarity	NPC261380
0.7672	Intermediate Similarity	NPC477092
0.7672	Intermediate Similarity	NPC236918
0.7672	Intermediate Similarity	NPC61520
0.7672	Intermediate Similarity	NPC156745
0.767	Intermediate Similarity	NPC153590
0.767	Intermediate Similarity	NPC60386
0.767	Intermediate Similarity	NPC473273
0.767	Intermediate Similarity	NPC473234
0.767	Intermediate Similarity	NPC473263
0.767	Intermediate Similarity	NPC475912
0.767	Intermediate Similarity	NPC308656

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 NPC309190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1238
0.2-0.3	3397
0.3-0.4	2766
0.4-0.5	1014
0.5-0.6	300
0.6-0.7	213
0.7-0.8	59
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8218	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5785	Approved
0.7909	Intermediate Similarity	NPD6371	Approved
0.7677	Intermediate Similarity	NPD5363	Approved
0.76	Intermediate Similarity	NPD5786	Approved
0.7573	Intermediate Similarity	NPD6411	Approved
0.75	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD5778	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.7404	Intermediate Similarity	NPD7637	Suspended
0.7379	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6101	Approved
0.7374	Intermediate Similarity	NPD4270	Approved
0.7374	Intermediate Similarity	NPD4269	Approved
0.7321	Intermediate Similarity	NPD5697	Approved
0.7321	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4225	Approved
0.7304	Intermediate Similarity	NPD6053	Discontinued
0.73	Intermediate Similarity	NPD5362	Discontinued
0.7273	Intermediate Similarity	NPD5369	Approved
0.7257	Intermediate Similarity	NPD6899	Approved
0.7257	Intermediate Similarity	NPD6881	Approved
0.7238	Intermediate Similarity	NPD7983	Approved
0.7217	Intermediate Similarity	NPD6650	Approved
0.7217	Intermediate Similarity	NPD6649	Approved
0.72	Intermediate Similarity	NPD5209	Approved
0.72	Intermediate Similarity	NPD6435	Approved
0.7193	Intermediate Similarity	NPD6014	Approved
0.7193	Intermediate Similarity	NPD6012	Approved
0.7193	Intermediate Similarity	NPD6013	Approved
0.7172	Intermediate Similarity	NPD4820	Approved
0.7172	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4252	Approved
0.7172	Intermediate Similarity	NPD4822	Approved
0.7172	Intermediate Similarity	NPD4821	Approved
0.7172	Intermediate Similarity	NPD4819	Approved
0.7143	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6883	Approved
0.713	Intermediate Similarity	NPD7102	Approved
0.713	Intermediate Similarity	NPD7290	Approved
0.713	Intermediate Similarity	NPD7839	Suspended
0.7117	Intermediate Similarity	NPD5211	Phase 2
0.7105	Intermediate Similarity	NPD6011	Approved
0.7103	Intermediate Similarity	NPD5282	Discontinued
0.708	Intermediate Similarity	NPD6402	Approved
0.708	Intermediate Similarity	NPD5739	Approved
0.708	Intermediate Similarity	NPD6675	Approved
0.708	Intermediate Similarity	NPD7128	Approved
0.7075	Intermediate Similarity	NPD5281	Approved
0.7075	Intermediate Similarity	NPD5284	Approved
0.7069	Intermediate Similarity	NPD8130	Phase 1
0.7069	Intermediate Similarity	NPD6847	Approved
0.7069	Intermediate Similarity	NPD6617	Approved
0.7069	Intermediate Similarity	NPD6869	Approved
0.7043	Intermediate Similarity	NPD6372	Approved
0.7043	Intermediate Similarity	NPD6373	Approved
0.7018	Intermediate Similarity	NPD5701	Approved
0.7009	Intermediate Similarity	NPD8297	Approved
0.7009	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD5368	Approved
0.7	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5141	Approved
0.699	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD46	Approved
0.6981	Remote Similarity	NPD6698	Approved
0.697	Remote Similarity	NPD4271	Approved
0.697	Remote Similarity	NPD4268	Approved
0.6961	Remote Similarity	NPD7154	Phase 3
0.6957	Remote Similarity	NPD7320	Approved
0.6937	Remote Similarity	NPD5286	Approved
0.6937	Remote Similarity	NPD4696	Approved
0.6937	Remote Similarity	NPD5285	Approved
0.6909	Remote Similarity	NPD6083	Phase 2
0.6909	Remote Similarity	NPD6084	Phase 2
0.6887	Remote Similarity	NPD1695	Approved
0.6885	Remote Similarity	NPD6319	Approved
0.6881	Remote Similarity	NPD5695	Phase 3
0.6863	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6399	Phase 3
0.685	Remote Similarity	NPD7319	Approved
0.6847	Remote Similarity	NPD5696	Approved
0.6829	Remote Similarity	NPD8515	Approved
0.6829	Remote Similarity	NPD8517	Approved
0.6829	Remote Similarity	NPD8516	Approved
0.6829	Remote Similarity	NPD8513	Phase 3
0.6827	Remote Similarity	NPD1694	Approved
0.6822	Remote Similarity	NPD7838	Discovery
0.6814	Remote Similarity	NPD5224	Approved
0.6814	Remote Similarity	NPD5225	Approved
0.6814	Remote Similarity	NPD5226	Approved
0.6814	Remote Similarity	NPD4633	Approved
0.681	Remote Similarity	NPD6686	Approved
0.6796	Remote Similarity	NPD5332	Approved
0.6796	Remote Similarity	NPD5331	Approved
0.6786	Remote Similarity	NPD7640	Approved
0.6786	Remote Similarity	NPD7639	Approved
0.6765	Remote Similarity	NPD4790	Discontinued
0.6762	Remote Similarity	NPD4249	Approved
0.6757	Remote Similarity	NPD4755	Approved
0.6754	Remote Similarity	NPD5174	Approved
0.6754	Remote Similarity	NPD5175	Approved
0.6746	Remote Similarity	NPD7507	Approved
0.6731	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4629	Approved
0.6727	Remote Similarity	NPD5210	Approved
0.6726	Remote Similarity	NPD5223	Approved
0.6698	Remote Similarity	NPD4250	Approved
0.6698	Remote Similarity	NPD4251	Approved
0.6696	Remote Similarity	NPD7638	Approved
0.6695	Remote Similarity	NPD4634	Approved
0.6694	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6639	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6317	Approved
0.6638	Remote Similarity	NPD6008	Approved
0.6637	Remote Similarity	NPD4700	Approved
0.6635	Remote Similarity	NPD6695	Phase 3
0.6615	Remote Similarity	NPD7260	Phase 2
0.6614	Remote Similarity	NPD6616	Approved
0.6613	Remote Similarity	NPD6054	Approved
0.6606	Remote Similarity	NPD5694	Approved
0.6606	Remote Similarity	NPD5693	Phase 1
0.6606	Remote Similarity	NPD6079	Approved
0.6604	Remote Similarity	NPD5279	Phase 3
0.6585	Remote Similarity	NPD6335	Approved
0.6585	Remote Similarity	NPD6314	Approved
0.6585	Remote Similarity	NPD6313	Approved
0.6574	Remote Similarity	NPD4753	Phase 2
0.6562	Remote Similarity	NPD7078	Approved
0.6562	Remote Similarity	NPD8074	Phase 3
0.656	Remote Similarity	NPD7503	Approved
0.656	Remote Similarity	NPD6016	Approved
0.656	Remote Similarity	NPD6015	Approved
0.656	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4730	Approved
0.6525	Remote Similarity	NPD4729	Approved
0.6518	Remote Similarity	NPD5221	Approved
0.6518	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5222	Approved
0.6514	Remote Similarity	NPD5692	Phase 3
0.6512	Remote Similarity	NPD7736	Approved
0.6509	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6370	Approved
0.6508	Remote Similarity	NPD5988	Approved
0.6504	Remote Similarity	NPD6009	Approved
0.65	Remote Similarity	NPD8039	Approved
0.65	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6648	Approved
0.6481	Remote Similarity	NPD4518	Approved
0.646	Remote Similarity	NPD5173	Approved
0.6455	Remote Similarity	NPD6050	Approved
0.6455	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5330	Approved
0.6449	Remote Similarity	NPD7334	Approved
0.6449	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6409	Approved
0.6449	Remote Similarity	NPD7146	Approved
0.6449	Remote Similarity	NPD7521	Approved
0.6449	Remote Similarity	NPD6684	Approved
0.6435	Remote Similarity	NPD5344	Discontinued
0.6429	Remote Similarity	NPD5983	Phase 2
0.6422	Remote Similarity	NPD5370	Suspended
0.6422	Remote Similarity	NPD5328	Approved
0.6417	Remote Similarity	NPD5249	Phase 3
0.6417	Remote Similarity	NPD5250	Approved
0.6417	Remote Similarity	NPD5248	Approved
0.6417	Remote Similarity	NPD5251	Approved
0.6417	Remote Similarity	NPD5247	Approved
0.6415	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD3666	Approved
0.6415	Remote Similarity	NPD3665	Phase 1
0.6415	Remote Similarity	NPD3133	Approved
0.6396	Remote Similarity	NPD4202	Approved
0.6389	Remote Similarity	NPD7750	Discontinued
0.6389	Remote Similarity	NPD7524	Approved
0.6387	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5128	Approved
0.6372	Remote Similarity	NPD4697	Phase 3
0.637	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5216	Approved
0.6364	Remote Similarity	NPD5217	Approved
0.6364	Remote Similarity	NPD5215	Approved
0.6356	Remote Similarity	NPD4767	Approved
0.6356	Remote Similarity	NPD4768	Approved
0.6349	Remote Similarity	NPD6059	Approved
0.6346	Remote Similarity	NPD7514	Phase 3
0.6346	Remote Similarity	NPD6930	Phase 2
0.6346	Remote Similarity	NPD6931	Approved
0.633	Remote Similarity	NPD6903	Approved
0.633	Remote Similarity	NPD5737	Approved
0.633	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6672	Approved
0.6328	Remote Similarity	NPD7829	Approved
0.6328	Remote Similarity	NPD7830	Approved
0.6328	Remote Similarity	NPD7604	Phase 2
0.6325	Remote Similarity	NPD4754	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