NPASS Compound

Structure

CID191899 OpenBabel06191715572D 27 30 0 0 1 0 0 0 0 0999 V2000 -0.0428 -1.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5020 -0.4448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6788 -1.8969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6803 -1.1607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8577 -0.6461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6779 -2.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3737 0.6223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2357 0.0175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9869 1.1073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9913 -0.9527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6712 -0.9332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8328 -0.4580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1421 -0.4713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1344 0.5048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8251 0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9759 0.9995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3837 -1.0858 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4303 -0.8762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2353 -0.0433 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4167 0.8828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6767 -0.2517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3665 1.1073 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6559 1.0066 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9683 1.9632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1600 1.5945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6084 -2.0357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 11 1 0 0 0 0 3 11 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 6 26 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 21 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 12 15 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 6 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 21 1 0 0 0 0 19 22 1 6 0 0 0 20 22 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 22 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.21
Volume:	388.248
LogP:	4.355
LogD:	3.384
LogS:	-4.046
# Rotatable Bonds:	3
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.609
Synthetic Accessibility Score:	5.126
Fsp3:	0.682
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.713
MDCK Permeability:	2.230648351542186e-05
Pgp-inhibitor:	0.896
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.342
30% Bioavailability (F30%):	0.124

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.587
Plasma Protein Binding (PPB):	98.67050170898438%
Volume Distribution (VD):	1.686
Pgp-substrate:	2.463101863861084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.785
CYP2C19-inhibitor:	0.253
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.648
CYP2C9-substrate:	0.696
CYP2D6-inhibitor:	0.133
CYP2D6-substrate:	0.263
CYP3A4-inhibitor:	0.366
CYP3A4-substrate:	0.482

ADMET: Excretion

Clearance (CL):	4.802
Half-life (T1/2):	0.073

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.457
Drug-inuced Liver Injury (DILI):	0.097
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.803
Maximum Recommended Daily Dose:	0.49
Skin Sensitization:	0.924
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.758
Respiratory Toxicity:	0.816

Download Data

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

Natural Product: NPC191899

Natural Product ID:	NPC191899
*Common Name:**	HEUIVINVBVPWCU-WEMPKCCASA-N
IUPAC Name:	n.a.
Synonyms:	7-O-Ethylrosmanol
Standard InCHIKey:	HEUIVINVBVPWCU-WEMPKCCASA-N
Standard InCHI:	InChI=1S/C22H30O5/c1-6-26-17-13-10-12(11(2)3)15(23)16(24)14(13)22-9-7-8-21(4,5)19(22)18(17)27-20(22)25/h10-11,17-19,23-24H,6-9H2,1-5H3/t17-,18+,19-,22-/m0/s1
SMILES:	CCO[C@H]1c2cc(C(C)C)c(c(c2[C@@]23CCCC(C)(C)[C@@H]2[C@@H]1OC3=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464584
PubChem CID:	23243693
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
NPO17119	Dalea versicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043439]
NPO18606	Achyrocline bogotensis	Species	Asteraceae	Eukaryota	n.a.	Colombian	n.a.	PMID[15844937]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	root	n.a.	PMID[18401845]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19775092]
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	aerial parts	Shangrila, Yunnan Province, China	2008-AUG	PMID[21534539]
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21534539]
NPO12148.2	Acer pictum subsp. okamotoanum	Subspecies	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461665]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18356	Stachys tuberifera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18435	Tylophora atrofolliculata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18356	Stachys tuberifera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18435	Tylophora atrofolliculata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2377	Cetraria ciliaris	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18435	Tylophora atrofolliculata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13414	Senecio fuertesii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18606	Achyrocline bogotensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19580	Chamaemelum fuscatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19777	Pholiota adiposa	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4984	Salvia cana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12148.2	Acer pictum subsp. okamotoanum	Subspecies	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19638	Scutellaria albida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17119	Dalea versicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4230	Protoparmeliopsis peltata	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13832	Aspilia hispida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19522	Arthropsis truncata	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19311	Dasymaschalon blumei	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17783	Sideritis cystosiphon	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10852	Felimare midatlantica	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16997	Talaromyces aculeatus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17643	Penicillium pedemontanum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16990	Verbesina virgata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18356	Stachys tuberifera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17911	Blepharisma japonicum	Species	Blepharismidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16567	Doriopsilla areolata	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15497	Caria ino	Species	Riodinidae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	IC90	=	1.7	ug.mL-1	PMID[473254]

☑ 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 NPC191899 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	315
0.1-0.2	1210
0.2-0.3	2634
0.3-0.4	5000
0.4-0.5	9804
0.5-0.6	8648
0.6-0.7	10024
0.7-0.8	4909
0.8-0.85	115
0.85-0.9	24
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC246229
0.9714	High Similarity	NPC126707
0.9577	High Similarity	NPC474991
0.951	High Similarity	NPC127046
0.9507	High Similarity	NPC84786
0.9362	High Similarity	NPC272907
0.9362	High Similarity	NPC2681
0.9306	High Similarity	NPC58752
0.9241	High Similarity	NPC470757
0.9137	High Similarity	NPC293454
0.9048	High Similarity	NPC471852
0.9021	High Similarity	NPC3218
0.8973	High Similarity	NPC75295
0.8859	High Similarity	NPC142654
0.8844	High Similarity	NPC258856
0.8759	High Similarity	NPC475907
0.875	High Similarity	NPC62051
0.8742	High Similarity	NPC124842
0.8733	High Similarity	NPC303989
0.8662	High Similarity	NPC49742
0.8652	High Similarity	NPC291001
0.8652	High Similarity	NPC78575
0.8652	High Similarity	NPC312341
0.863	High Similarity	NPC471853
0.859	High Similarity	NPC21046
0.8581	High Similarity	NPC143328
0.8562	High Similarity	NPC65591
0.8562	High Similarity	NPC178574
0.8514	High Similarity	NPC248068
0.8503	High Similarity	NPC29599
0.8503	High Similarity	NPC327187
0.8483	Intermediate Similarity	NPC326847
0.8477	Intermediate Similarity	NPC5568
0.8472	Intermediate Similarity	NPC213122
0.8462	Intermediate Similarity	NPC59239
0.8451	Intermediate Similarity	NPC99795
0.84	Intermediate Similarity	NPC309169
0.84	Intermediate Similarity	NPC196941
0.8377	Intermediate Similarity	NPC221249
0.8365	Intermediate Similarity	NPC144843
0.8356	Intermediate Similarity	NPC68292
0.8356	Intermediate Similarity	NPC475111
0.8355	Intermediate Similarity	NPC52692
0.8344	Intermediate Similarity	NPC167098
0.8344	Intermediate Similarity	NPC296044
0.8333	Intermediate Similarity	NPC472835
0.8333	Intermediate Similarity	NPC165612
0.8323	Intermediate Similarity	NPC200726
0.8313	Intermediate Similarity	NPC173729
0.8313	Intermediate Similarity	NPC223006
0.8313	Intermediate Similarity	NPC272750
0.8313	Intermediate Similarity	NPC25889
0.8313	Intermediate Similarity	NPC134047
0.8313	Intermediate Similarity	NPC100420
0.8302	Intermediate Similarity	NPC469889
0.8302	Intermediate Similarity	NPC266365
0.8299	Intermediate Similarity	NPC308976
0.8291	Intermediate Similarity	NPC471750
0.8289	Intermediate Similarity	NPC169682
0.8276	Intermediate Similarity	NPC239855
0.8276	Intermediate Similarity	NPC111845
0.8276	Intermediate Similarity	NPC476282
0.8272	Intermediate Similarity	NPC177362
0.8267	Intermediate Similarity	NPC314271
0.8267	Intermediate Similarity	NPC184935
0.8258	Intermediate Similarity	NPC270268
0.8258	Intermediate Similarity	NPC267091
0.8255	Intermediate Similarity	NPC100675
0.825	Intermediate Similarity	NPC144557
0.8247	Intermediate Similarity	NPC261322
0.8247	Intermediate Similarity	NPC474305
0.8243	Intermediate Similarity	NPC230811
0.8239	Intermediate Similarity	NPC268718
0.8239	Intermediate Similarity	NPC150943
0.8239	Intermediate Similarity	NPC47623
0.8239	Intermediate Similarity	NPC91634
0.8239	Intermediate Similarity	NPC471077
0.8235	Intermediate Similarity	NPC53362
0.8235	Intermediate Similarity	NPC166583
0.8228	Intermediate Similarity	NPC163527
0.8228	Intermediate Similarity	NPC181168
0.8228	Intermediate Similarity	NPC115281
0.8221	Intermediate Similarity	NPC266545
0.8221	Intermediate Similarity	NPC202428
0.8217	Intermediate Similarity	NPC471456
0.821	Intermediate Similarity	NPC263212
0.8205	Intermediate Similarity	NPC180388
0.8205	Intermediate Similarity	NPC131121
0.8199	Intermediate Similarity	NPC45943
0.8194	Intermediate Similarity	NPC243891
0.8194	Intermediate Similarity	NPC31132
0.8193	Intermediate Similarity	NPC475054
0.8182	Intermediate Similarity	NPC474306
0.8182	Intermediate Similarity	NPC475848
0.8176	Intermediate Similarity	NPC470339
0.8176	Intermediate Similarity	NPC471152
0.8171	Intermediate Similarity	NPC91043
0.817	Intermediate Similarity	NPC63918
0.8169	Intermediate Similarity	NPC253681
0.8165	Intermediate Similarity	NPC109765
0.8165	Intermediate Similarity	NPC165483
0.8165	Intermediate Similarity	NPC150227
0.8163	Intermediate Similarity	NPC153088
0.8158	Intermediate Similarity	NPC471305
0.8158	Intermediate Similarity	NPC260152
0.8158	Intermediate Similarity	NPC223185
0.8153	Intermediate Similarity	NPC125487
0.8153	Intermediate Similarity	NPC281703
0.8153	Intermediate Similarity	NPC30009
0.8153	Intermediate Similarity	NPC103197
0.8151	Intermediate Similarity	NPC227719
0.8151	Intermediate Similarity	NPC138472
0.8146	Intermediate Similarity	NPC477873
0.8146	Intermediate Similarity	NPC469447
0.8141	Intermediate Similarity	NPC75377
0.8138	Intermediate Similarity	NPC318799
0.8138	Intermediate Similarity	NPC243305
0.8137	Intermediate Similarity	NPC116838
0.8137	Intermediate Similarity	NPC22130
0.8133	Intermediate Similarity	NPC38473
0.8129	Intermediate Similarity	NPC478219
0.8129	Intermediate Similarity	NPC327962
0.8125	Intermediate Similarity	NPC472055
0.8125	Intermediate Similarity	NPC131684
0.8117	Intermediate Similarity	NPC81835
0.8113	Intermediate Similarity	NPC207584
0.8113	Intermediate Similarity	NPC202495
0.8113	Intermediate Similarity	NPC77679
0.8113	Intermediate Similarity	NPC19947
0.8113	Intermediate Similarity	NPC84935
0.8113	Intermediate Similarity	NPC302258
0.8113	Intermediate Similarity	NPC190020
0.811	Intermediate Similarity	NPC117911
0.8105	Intermediate Similarity	NPC225351
0.8105	Intermediate Similarity	NPC470038
0.8105	Intermediate Similarity	NPC8102
0.8105	Intermediate Similarity	NPC66894
0.8101	Intermediate Similarity	NPC79998
0.8101	Intermediate Similarity	NPC203757
0.8101	Intermediate Similarity	NPC300757
0.8101	Intermediate Similarity	NPC180901
0.8101	Intermediate Similarity	NPC199926
0.8099	Intermediate Similarity	NPC124030
0.8099	Intermediate Similarity	NPC137750
0.8098	Intermediate Similarity	NPC472452
0.8098	Intermediate Similarity	NPC255787
0.8095	Intermediate Similarity	NPC477893
0.8095	Intermediate Similarity	NPC300776
0.8095	Intermediate Similarity	NPC176814
0.8095	Intermediate Similarity	NPC477896
0.8095	Intermediate Similarity	NPC5310
0.8095	Intermediate Similarity	NPC68779
0.8095	Intermediate Similarity	NPC471942
0.8095	Intermediate Similarity	NPC4982
0.8092	Intermediate Similarity	NPC469615
0.8092	Intermediate Similarity	NPC470130
0.8089	Intermediate Similarity	NPC245948
0.8089	Intermediate Similarity	NPC295646
0.8086	Intermediate Similarity	NPC116759
0.8086	Intermediate Similarity	NPC14294
0.8084	Intermediate Similarity	NPC196771
0.8082	Intermediate Similarity	NPC476389
0.8079	Intermediate Similarity	NPC253481
0.8079	Intermediate Similarity	NPC131971
0.8079	Intermediate Similarity	NPC31751
0.8079	Intermediate Similarity	NPC253722
0.8077	Intermediate Similarity	NPC50269
0.8075	Intermediate Similarity	NPC216916
0.8075	Intermediate Similarity	NPC177100
0.8075	Intermediate Similarity	NPC139540
0.8075	Intermediate Similarity	NPC477627
0.8071	Intermediate Similarity	NPC249340
0.8071	Intermediate Similarity	NPC162935
0.8067	Intermediate Similarity	NPC191280
0.8067	Intermediate Similarity	NPC147379
0.8063	Intermediate Similarity	NPC472299
0.8063	Intermediate Similarity	NPC239118
0.8063	Intermediate Similarity	NPC218818
0.8063	Intermediate Similarity	NPC4950
0.8061	Intermediate Similarity	NPC472803
0.8054	Intermediate Similarity	NPC119542
0.8054	Intermediate Similarity	NPC281780
0.8052	Intermediate Similarity	NPC268366
0.805	Intermediate Similarity	NPC237946
0.805	Intermediate Similarity	NPC478223
0.805	Intermediate Similarity	NPC32373
0.8049	Intermediate Similarity	NPC473094
0.8049	Intermediate Similarity	NPC107009
0.8049	Intermediate Similarity	NPC215802
0.8049	Intermediate Similarity	NPC167231
0.8041	Intermediate Similarity	NPC252343
0.8039	Intermediate Similarity	NPC469683
0.8039	Intermediate Similarity	NPC53520
0.8039	Intermediate Similarity	NPC213900
0.8038	Intermediate Similarity	NPC273578
0.8037	Intermediate Similarity	NPC473286
0.8037	Intermediate Similarity	NPC102372
0.8037	Intermediate Similarity	NPC41689
0.8036	Intermediate Similarity	NPC260300
0.8036	Intermediate Similarity	NPC469418

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 NPC191899 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	768
0.2-0.3	1584
0.3-0.4	2580
0.4-0.5	2203
0.5-0.6	1182
0.6-0.7	494
0.7-0.8	80
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8291	Intermediate Similarity	NPD6234	Discontinued
0.8089	Intermediate Similarity	NPD37	Approved
0.805	Intermediate Similarity	NPD4965	Approved
0.805	Intermediate Similarity	NPD4966	Approved
0.805	Intermediate Similarity	NPD4967	Phase 2
0.7961	Intermediate Similarity	NPD8166	Discontinued
0.7939	Intermediate Similarity	NPD7228	Approved
0.7914	Intermediate Similarity	NPD6232	Discontinued
0.7879	Intermediate Similarity	NPD7473	Discontinued
0.7871	Intermediate Similarity	NPD2532	Approved
0.7871	Intermediate Similarity	NPD2534	Approved
0.7871	Intermediate Similarity	NPD2533	Approved
0.7871	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6190	Approved
0.7784	Intermediate Similarity	NPD5844	Phase 1
0.7778	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6663	Approved
0.7756	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5736	Approved
0.7727	Intermediate Similarity	NPD4628	Phase 3
0.7692	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD230	Phase 1
0.7644	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7199	Phase 2
0.76	Intermediate Similarity	NPD3620	Phase 2
0.76	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3764	Approved
0.7545	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD8127	Discontinued
0.7517	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4110	Phase 3
0.7483	Intermediate Similarity	NPD4060	Phase 1
0.7453	Intermediate Similarity	NPD7458	Discontinued
0.7442	Intermediate Similarity	NPD7240	Approved
0.7436	Intermediate Similarity	NPD6674	Discontinued
0.7431	Intermediate Similarity	NPD3019	Approved
0.7429	Intermediate Similarity	NPD8150	Discontinued
0.7423	Intermediate Similarity	NPD1934	Approved
0.7415	Intermediate Similarity	NPD1283	Approved
0.7389	Intermediate Similarity	NPD7003	Approved
0.7381	Intermediate Similarity	NPD7229	Phase 3
0.7378	Intermediate Similarity	NPD1465	Phase 2
0.7368	Intermediate Similarity	NPD2979	Phase 3
0.7355	Intermediate Similarity	NPD2438	Suspended
0.7355	Intermediate Similarity	NPD6099	Approved
0.7355	Intermediate Similarity	NPD6100	Approved
0.7351	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3226	Approved
0.7325	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6355	Discontinued
0.7314	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2932	Approved
0.731	Intermediate Similarity	NPD3818	Discontinued
0.7289	Intermediate Similarity	NPD3882	Suspended
0.7283	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5710	Approved
0.7278	Intermediate Similarity	NPD5711	Approved
0.7273	Intermediate Similarity	NPD2801	Approved
0.7267	Intermediate Similarity	NPD6273	Approved
0.7262	Intermediate Similarity	NPD5494	Approved
0.7261	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4140	Approved
0.7248	Intermediate Similarity	NPD3094	Phase 2
0.7244	Intermediate Similarity	NPD5404	Approved
0.7244	Intermediate Similarity	NPD5408	Approved
0.7244	Intermediate Similarity	NPD5406	Approved
0.7244	Intermediate Similarity	NPD5405	Approved
0.7237	Intermediate Similarity	NPD6798	Discontinued
0.7219	Intermediate Similarity	NPD6959	Discontinued
0.7211	Intermediate Similarity	NPD1281	Approved
0.7211	Intermediate Similarity	NPD3092	Approved
0.7207	Intermediate Similarity	NPD2488	Approved
0.7207	Intermediate Similarity	NPD2490	Approved
0.7197	Intermediate Similarity	NPD6004	Phase 3
0.7197	Intermediate Similarity	NPD2346	Discontinued
0.7197	Intermediate Similarity	NPD5762	Approved
0.7197	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7266	Discontinued
0.7197	Intermediate Similarity	NPD6005	Phase 3
0.7197	Intermediate Similarity	NPD6002	Phase 3
0.7197	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5763	Approved
0.7193	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6166	Phase 2
0.7193	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD8032	Phase 2
0.7179	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7819	Suspended
0.7167	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1608	Approved
0.7159	Intermediate Similarity	NPD8313	Approved
0.7159	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7135	Intermediate Similarity	NPD2494	Approved
0.7135	Intermediate Similarity	NPD2493	Approved
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7134	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2629	Approved
0.7126	Intermediate Similarity	NPD3817	Phase 2
0.712	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4582	Approved
0.7112	Intermediate Similarity	NPD4583	Approved
0.7091	Intermediate Similarity	NPD4380	Phase 2
0.7091	Intermediate Similarity	NPD6599	Discontinued
0.7089	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4198	Discontinued
0.7075	Intermediate Similarity	NPD4626	Approved
0.7075	Intermediate Similarity	NPD5125	Phase 3
0.7075	Intermediate Similarity	NPD5126	Approved
0.7075	Intermediate Similarity	NPD1778	Approved
0.7067	Intermediate Similarity	NPD6696	Suspended
0.7066	Intermediate Similarity	NPD8455	Phase 2
0.7066	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7095	Approved
0.7059	Intermediate Similarity	NPD4002	Approved
0.7059	Intermediate Similarity	NPD3027	Phase 3
0.7059	Intermediate Similarity	NPD4004	Approved
0.7055	Intermediate Similarity	NPD3091	Approved
0.7055	Intermediate Similarity	NPD9545	Approved
0.7045	Intermediate Similarity	NPD6559	Discontinued
0.7043	Intermediate Similarity	NPD3452	Approved
0.7043	Intermediate Similarity	NPD3450	Approved
0.7037	Intermediate Similarity	NPD7390	Discontinued
0.7037	Intermediate Similarity	NPD1511	Approved
0.7032	Intermediate Similarity	NPD1613	Approved
0.7032	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7074	Phase 3
0.7027	Intermediate Similarity	NPD3023	Approved
0.7027	Intermediate Similarity	NPD3026	Approved
0.7025	Intermediate Similarity	NPD2935	Discontinued
0.7025	Intermediate Similarity	NPD2531	Phase 2
0.7013	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7985	Registered
0.7012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5691	Approved
0.7007	Intermediate Similarity	NPD3025	Approved
0.7007	Intermediate Similarity	NPD3024	Approved
0.7006	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2800	Approved
0.6988	Remote Similarity	NPD7028	Phase 2
0.6987	Remote Similarity	NPD5735	Approved
0.698	Remote Similarity	NPD3705	Approved
0.6975	Remote Similarity	NPD7236	Approved
0.6971	Remote Similarity	NPD7054	Approved
0.6968	Remote Similarity	NPD7680	Approved
0.6968	Remote Similarity	NPD6233	Phase 2
0.6962	Remote Similarity	NPD7033	Discontinued
0.6959	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD17	Approved
0.6951	Remote Similarity	NPD1512	Approved
0.6948	Remote Similarity	NPD7008	Discontinued
0.6933	Remote Similarity	NPD9269	Phase 2
0.6932	Remote Similarity	NPD7472	Approved
0.6928	Remote Similarity	NPD2861	Phase 2
0.6928	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD9494	Approved
0.6928	Remote Similarity	NPD3455	Phase 2
0.6923	Remote Similarity	NPD943	Approved
0.6923	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2974	Approved
0.6919	Remote Similarity	NPD2973	Approved
0.6919	Remote Similarity	NPD2975	Approved
0.6918	Remote Similarity	NPD4476	Approved
0.6918	Remote Similarity	NPD4477	Approved
0.6914	Remote Similarity	NPD7177	Discontinued
0.6908	Remote Similarity	NPD1470	Approved
0.6905	Remote Similarity	NPD6801	Discontinued
0.6902	Remote Similarity	NPD6534	Approved
0.6902	Remote Similarity	NPD6535	Approved
0.6901	Remote Similarity	NPD3021	Approved
0.6901	Remote Similarity	NPD3022	Approved
0.6899	Remote Similarity	NPD7097	Phase 1
0.6898	Remote Similarity	NPD4580	Approved
0.6893	Remote Similarity	NPD6797	Phase 2
0.6892	Remote Similarity	NPD1651	Approved
0.689	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3657	Discovery
0.6879	Remote Similarity	NPD3787	Discontinued
0.6875	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2971	Approved
0.6872	Remote Similarity	NPD2968	Approved
0.6867	Remote Similarity	NPD1201	Approved
0.6867	Remote Similarity	NPD7239	Suspended
0.6855	Remote Similarity	NPD2799	Discontinued
0.6855	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7251	Discontinued
0.6852	Remote Similarity	NPD3750	Approved
0.6846	Remote Similarity	NPD3095	Discontinued
0.6845	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7411	Suspended
0.6842	Remote Similarity	NPD8319	Approved
0.6842	Remote Similarity	NPD3749	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