NPASS Compound

Structure

CID48107 OpenBabel06191715382D 24 26 0 0 1 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 -3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 -2.5981 0.5000 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 -0.0000 -1.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0981 -2.3660 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 12 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 21 2 0 0 0 0 15 18 1 1 0 0 0 15 19 1 0 0 0 0 16 18 1 1 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 1 0 0 0 20 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	356.058
LogP:	2.629
LogD:	1.892
LogS:	-3.734
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.809
Synthetic Accessibility Score:	4.474
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.17
MDCK Permeability:	2.453541492286604e-05
Pgp-inhibitor:	0.032
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.136
Plasma Protein Binding (PPB):	91.94152069091797%
Volume Distribution (VD):	0.354
Pgp-substrate:	9.324495315551758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.767
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.668
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.524
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.071
CYP3A4-substrate:	0.165

ADMET: Excretion

Clearance (CL):	1.256
Half-life (T1/2):	0.561

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.185
Maximum Recommended Daily Dose:	0.186
Skin Sensitization:	0.558
Carcinogencity:	0.085
Eye Corrosion:	0.183
Eye Irritation:	0.866
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC48107

Natural Product ID:	NPC48107
*Common Name:**	BDGVLOCEQIJJDJ-AFKBCAQJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BDGVLOCEQIJJDJ-AFKBCAQJSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-12(2)13-11-20(24)9-6-15-18(3,16(20)10-14(13)21)7-5-8-19(15,4)17(22)23/h11-12,15-16,24H,5-10H2,1-4H3,(H,22,23)/t15-,16-,18+,19-,20+/m1/s1
SMILES:	CC(C)C1=C[C@]2(CC[C@@H]3[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3797727
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1324982]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[13465274]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1536925]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180822]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512094]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19376614]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	trunk	n.a.	n.a.	PMID[24224862]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	seed	n.a.	PMID[24225786]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	Trunk	n.a.	n.a.	PMID[26812172]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30063340]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3509958]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4949	Salvia yosgadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2993	0totodarus sloanii	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3554	Aonidiella aurantii	Species	Diaspididae	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	5
Others	2

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	166.1	%	PMID[467946]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	91.2	%	PMID[467946]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[467946]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[467946]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	56100.0	nM	PMID[467946]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[467946]

☑ 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 NPC48107 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	196
0.1-0.2	1183
0.2-0.3	4467
0.3-0.4	10617
0.4-0.5	12262
0.5-0.6	6775
0.6-0.7	4714
0.7-0.8	2211
0.8-0.85	218
0.85-0.9	48
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8953	High Similarity	NPC476409
0.8929	High Similarity	NPC49019
0.8916	High Similarity	NPC278459
0.8902	High Similarity	NPC170394
0.8901	High Similarity	NPC170131
0.8851	High Similarity	NPC72397
0.8804	High Similarity	NPC478056
0.8795	High Similarity	NPC476809
0.8795	High Similarity	NPC469637
0.878	High Similarity	NPC198240
0.875	High Similarity	NPC262043
0.875	High Similarity	NPC36668
0.875	High Similarity	NPC118011
0.8736	High Similarity	NPC136948
0.8736	High Similarity	NPC471792
0.869	High Similarity	NPC226068
0.869	High Similarity	NPC473217
0.8667	High Similarity	NPC131840
0.8667	High Similarity	NPC476416
0.8659	High Similarity	NPC257666
0.8659	High Similarity	NPC266193
0.8659	High Similarity	NPC34110
0.8659	High Similarity	NPC61952
0.8659	High Similarity	NPC97377
0.8659	High Similarity	NPC165711
0.8636	High Similarity	NPC104560
0.8632	High Similarity	NPC478057
0.8621	High Similarity	NPC472869
0.8605	High Similarity	NPC248758
0.8556	High Similarity	NPC472978
0.8554	High Similarity	NPC74410
0.8539	High Similarity	NPC472973
0.8537	High Similarity	NPC186554
0.8537	High Similarity	NPC472305
0.8537	High Similarity	NPC180886
0.8537	High Similarity	NPC7629
0.8537	High Similarity	NPC76966
0.8537	High Similarity	NPC151622
0.8495	Intermediate Similarity	NPC253826
0.8488	Intermediate Similarity	NPC105803
0.8488	Intermediate Similarity	NPC297398
0.8488	Intermediate Similarity	NPC97913
0.8478	Intermediate Similarity	NPC53565
0.8478	Intermediate Similarity	NPC147232
0.8471	Intermediate Similarity	NPC471898
0.8462	Intermediate Similarity	NPC472871
0.8444	Intermediate Similarity	NPC476437
0.8444	Intermediate Similarity	NPC476369
0.8434	Intermediate Similarity	NPC132542
0.8427	Intermediate Similarity	NPC471793
0.8427	Intermediate Similarity	NPC473229
0.8427	Intermediate Similarity	NPC117122
0.8427	Intermediate Similarity	NPC471791
0.8427	Intermediate Similarity	NPC472870
0.8421	Intermediate Similarity	NPC81530
0.8415	Intermediate Similarity	NPC476795
0.8415	Intermediate Similarity	NPC39362
0.8409	Intermediate Similarity	NPC473226
0.8409	Intermediate Similarity	NPC73038
0.8409	Intermediate Similarity	NPC472974
0.8409	Intermediate Similarity	NPC322159
0.8409	Intermediate Similarity	NPC82979
0.8409	Intermediate Similarity	NPC472986
0.8409	Intermediate Similarity	NPC472985
0.8391	Intermediate Similarity	NPC164577
0.8391	Intermediate Similarity	NPC19849
0.8391	Intermediate Similarity	NPC476412
0.8391	Intermediate Similarity	NPC472865
0.8391	Intermediate Similarity	NPC472864
0.8391	Intermediate Similarity	NPC251170
0.8391	Intermediate Similarity	NPC96095
0.8387	Intermediate Similarity	NPC250757
0.8387	Intermediate Similarity	NPC301534
0.8372	Intermediate Similarity	NPC302661
0.8372	Intermediate Similarity	NPC238991
0.8372	Intermediate Similarity	NPC2524
0.837	Intermediate Similarity	NPC472976
0.837	Intermediate Similarity	NPC472977
0.837	Intermediate Similarity	NPC476415
0.8353	Intermediate Similarity	NPC37038
0.8352	Intermediate Similarity	NPC204341
0.8352	Intermediate Similarity	NPC158030
0.8352	Intermediate Similarity	NPC65120
0.8352	Intermediate Similarity	NPC252433
0.8352	Intermediate Similarity	NPC145067
0.8352	Intermediate Similarity	NPC289479
0.8352	Intermediate Similarity	NPC233455
0.8352	Intermediate Similarity	NPC4036
0.8333	Intermediate Similarity	NPC136289
0.8333	Intermediate Similarity	NPC477973
0.8333	Intermediate Similarity	NPC293753
0.8333	Intermediate Similarity	NPC179028
0.8333	Intermediate Similarity	NPC472983
0.8333	Intermediate Similarity	NPC471409
0.8333	Intermediate Similarity	NPC275494
0.8315	Intermediate Similarity	NPC181327
0.8315	Intermediate Similarity	NPC30421
0.8298	Intermediate Similarity	NPC473456
0.8295	Intermediate Similarity	NPC474680
0.8295	Intermediate Similarity	NPC474537
0.8295	Intermediate Similarity	NPC29447
0.828	Intermediate Similarity	NPC271195
0.828	Intermediate Similarity	NPC290481
0.8276	Intermediate Similarity	NPC102197
0.8276	Intermediate Similarity	NPC476927
0.8261	Intermediate Similarity	NPC214756
0.8261	Intermediate Similarity	NPC272075
0.8261	Intermediate Similarity	NPC472303
0.8261	Intermediate Similarity	NPC151722
0.8261	Intermediate Similarity	NPC295643
0.8256	Intermediate Similarity	NPC90055
0.8247	Intermediate Similarity	NPC95899
0.8242	Intermediate Similarity	NPC472866
0.8242	Intermediate Similarity	NPC291028
0.8242	Intermediate Similarity	NPC134321
0.8235	Intermediate Similarity	NPC192329
0.8235	Intermediate Similarity	NPC231431
0.8229	Intermediate Similarity	NPC282524
0.8229	Intermediate Similarity	NPC115862
0.8214	Intermediate Similarity	NPC472300
0.8211	Intermediate Similarity	NPC316598
0.8202	Intermediate Similarity	NPC472479
0.8202	Intermediate Similarity	NPC186975
0.8193	Intermediate Similarity	NPC279666
0.8193	Intermediate Similarity	NPC476346
0.8193	Intermediate Similarity	NPC192540
0.8191	Intermediate Similarity	NPC167193
0.8191	Intermediate Similarity	NPC117133
0.8191	Intermediate Similarity	NPC116457
0.8191	Intermediate Similarity	NPC235053
0.8191	Intermediate Similarity	NPC472941
0.8191	Intermediate Similarity	NPC456
0.8191	Intermediate Similarity	NPC472806
0.8172	Intermediate Similarity	NPC299100
0.8172	Intermediate Similarity	NPC279410
0.8172	Intermediate Similarity	NPC119562
0.8172	Intermediate Similarity	NPC8993
0.8172	Intermediate Similarity	NPC74751
0.8171	Intermediate Similarity	NPC109576
0.8171	Intermediate Similarity	NPC35656
0.8171	Intermediate Similarity	NPC180015
0.8171	Intermediate Similarity	NPC130016
0.8171	Intermediate Similarity	NPC56747
0.8171	Intermediate Similarity	NPC247586
0.8163	Intermediate Similarity	NPC472868
0.8161	Intermediate Similarity	NPC472239
0.8161	Intermediate Similarity	NPC472867
0.8161	Intermediate Similarity	NPC320514
0.8152	Intermediate Similarity	NPC110657
0.8152	Intermediate Similarity	NPC473998
0.8152	Intermediate Similarity	NPC86266
0.8152	Intermediate Similarity	NPC473986
0.8152	Intermediate Similarity	NPC116726
0.8152	Intermediate Similarity	NPC105189
0.8152	Intermediate Similarity	NPC475806
0.8152	Intermediate Similarity	NPC474018
0.8152	Intermediate Similarity	NPC472975
0.8152	Intermediate Similarity	NPC212301
0.8144	Intermediate Similarity	NPC234892
0.814	Intermediate Similarity	NPC472301
0.814	Intermediate Similarity	NPC172013
0.8132	Intermediate Similarity	NPC5509
0.8132	Intermediate Similarity	NPC309603
0.8132	Intermediate Similarity	NPC262858
0.8132	Intermediate Similarity	NPC472240
0.8132	Intermediate Similarity	NPC119416
0.8132	Intermediate Similarity	NPC473999
0.8132	Intermediate Similarity	NPC281524
0.8125	Intermediate Similarity	NPC154072
0.8125	Intermediate Similarity	NPC470074
0.8125	Intermediate Similarity	NPC476274
0.8125	Intermediate Similarity	NPC287833
0.8118	Intermediate Similarity	NPC207772
0.8118	Intermediate Similarity	NPC321514
0.8118	Intermediate Similarity	NPC260385
0.8118	Intermediate Similarity	NPC280654
0.8118	Intermediate Similarity	NPC476808
0.8118	Intermediate Similarity	NPC110094
0.8111	Intermediate Similarity	NPC236618
0.8111	Intermediate Similarity	NPC231599
0.8105	Intermediate Similarity	NPC320306
0.8105	Intermediate Similarity	NPC474343
0.8105	Intermediate Similarity	NPC89225
0.8105	Intermediate Similarity	NPC108078
0.8095	Intermediate Similarity	NPC69143
0.809	Intermediate Similarity	NPC476426
0.809	Intermediate Similarity	NPC269638
0.8085	Intermediate Similarity	NPC183012
0.8085	Intermediate Similarity	NPC266899
0.8085	Intermediate Similarity	NPC180950
0.8085	Intermediate Similarity	NPC476174
0.8085	Intermediate Similarity	NPC139570
0.8085	Intermediate Similarity	NPC148523
0.8085	Intermediate Similarity	NPC476245
0.8085	Intermediate Similarity	NPC139459
0.8072	Intermediate Similarity	NPC476046
0.8072	Intermediate Similarity	NPC103958
0.8072	Intermediate Similarity	NPC251970
0.8072	Intermediate Similarity	NPC161923
0.8072	Intermediate Similarity	NPC183503

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 NPC48107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	1548
0.2-0.3	3643
0.3-0.4	2408
0.4-0.5	881
0.5-0.6	230
0.6-0.7	130
0.7-0.8	115
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8409	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD7515	Phase 2
0.8315	Intermediate Similarity	NPD3573	Approved
0.8202	Intermediate Similarity	NPD4519	Discontinued
0.8202	Intermediate Similarity	NPD3618	Phase 1
0.8202	Intermediate Similarity	NPD4623	Approved
0.8172	Intermediate Similarity	NPD7748	Approved
0.814	Intermediate Similarity	NPD4695	Discontinued
0.8105	Intermediate Similarity	NPD7902	Approved
0.7957	Intermediate Similarity	NPD5284	Approved
0.7957	Intermediate Similarity	NPD5281	Approved
0.7955	Intermediate Similarity	NPD4223	Phase 3
0.7955	Intermediate Similarity	NPD4221	Approved
0.7789	Intermediate Similarity	NPD7900	Approved
0.7789	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4197	Approved
0.7778	Intermediate Similarity	NPD5211	Phase 2
0.7766	Intermediate Similarity	NPD6079	Approved
0.7742	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5328	Approved
0.7708	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5329	Approved
0.7684	Intermediate Similarity	NPD4202	Approved
0.7684	Intermediate Similarity	NPD6399	Phase 3
0.7664	Intermediate Similarity	NPD7115	Discovery
0.7653	Intermediate Similarity	NPD5696	Approved
0.7647	Intermediate Similarity	NPD5697	Approved
0.7629	Intermediate Similarity	NPD5221	Approved
0.7629	Intermediate Similarity	NPD4697	Phase 3
0.7629	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD5222	Approved
0.7624	Intermediate Similarity	NPD5141	Approved
0.7609	Intermediate Similarity	NPD4689	Approved
0.7609	Intermediate Similarity	NPD4688	Approved
0.7609	Intermediate Similarity	NPD4138	Approved
0.7609	Intermediate Similarity	NPD4693	Phase 3
0.7609	Intermediate Similarity	NPD4690	Approved
0.7609	Intermediate Similarity	NPD5690	Phase 2
0.7609	Intermediate Similarity	NPD5205	Approved
0.7604	Intermediate Similarity	NPD6001	Approved
0.7582	Intermediate Similarity	NPD3666	Approved
0.7582	Intermediate Similarity	NPD3133	Approved
0.7582	Intermediate Similarity	NPD3665	Phase 1
0.7579	Intermediate Similarity	NPD5693	Phase 1
0.7576	Intermediate Similarity	NPD7640	Approved
0.7576	Intermediate Similarity	NPD7639	Approved
0.7576	Intermediate Similarity	NPD5286	Approved
0.7576	Intermediate Similarity	NPD4696	Approved
0.7576	Intermediate Similarity	NPD5285	Approved
0.7573	Intermediate Similarity	NPD6011	Approved
0.7573	Intermediate Similarity	NPD6881	Approved
0.7573	Intermediate Similarity	NPD6899	Approved
0.7556	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3667	Approved
0.7553	Intermediate Similarity	NPD4753	Phase 2
0.7553	Intermediate Similarity	NPD6904	Approved
0.7553	Intermediate Similarity	NPD6673	Approved
0.7553	Intermediate Similarity	NPD6080	Approved
0.7551	Intermediate Similarity	NPD6083	Phase 2
0.7551	Intermediate Similarity	NPD6084	Phase 2
0.7551	Intermediate Similarity	NPD4755	Approved
0.7551	Intermediate Similarity	NPD5173	Approved
0.7549	Intermediate Similarity	NPD5739	Approved
0.7549	Intermediate Similarity	NPD6675	Approved
0.7549	Intermediate Similarity	NPD6402	Approved
0.7549	Intermediate Similarity	NPD7128	Approved
0.7526	Intermediate Similarity	NPD5695	Phase 3
0.7526	Intermediate Similarity	NPD5210	Approved
0.7526	Intermediate Similarity	NPD4629	Approved
0.7524	Intermediate Similarity	NPD6650	Approved
0.7524	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD1694	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.75	Intermediate Similarity	NPD3617	Approved
0.7476	Intermediate Similarity	NPD5701	Approved
0.7475	Intermediate Similarity	NPD4225	Approved
0.7475	Intermediate Similarity	NPD7638	Approved
0.7449	Intermediate Similarity	NPD7614	Phase 1
0.7447	Intermediate Similarity	NPD5208	Approved
0.7447	Intermediate Similarity	NPD5737	Approved
0.7447	Intermediate Similarity	NPD6672	Approved
0.7429	Intermediate Similarity	NPD7290	Approved
0.7429	Intermediate Similarity	NPD7102	Approved
0.7429	Intermediate Similarity	NPD6883	Approved
0.7426	Intermediate Similarity	NPD4633	Approved
0.7426	Intermediate Similarity	NPD5225	Approved
0.7426	Intermediate Similarity	NPD5224	Approved
0.7426	Intermediate Similarity	NPD5226	Approved
0.7419	Intermediate Similarity	NPD7334	Approved
0.7419	Intermediate Similarity	NPD7521	Approved
0.7419	Intermediate Similarity	NPD6684	Approved
0.7419	Intermediate Similarity	NPD5330	Approved
0.7419	Intermediate Similarity	NPD6409	Approved
0.7419	Intermediate Similarity	NPD5280	Approved
0.7419	Intermediate Similarity	NPD7146	Approved
0.7419	Intermediate Similarity	NPD4694	Approved
0.7416	Intermediate Similarity	NPD4195	Approved
0.7404	Intermediate Similarity	NPD7320	Approved
0.74	Intermediate Similarity	NPD4700	Approved
0.7391	Intermediate Similarity	NPD4786	Approved
0.7358	Intermediate Similarity	NPD8130	Phase 1
0.7358	Intermediate Similarity	NPD6617	Approved
0.7358	Intermediate Similarity	NPD6869	Approved
0.7358	Intermediate Similarity	NPD6847	Approved
0.7353	Intermediate Similarity	NPD5174	Approved
0.7353	Intermediate Similarity	NPD5175	Approved
0.7294	Intermediate Similarity	NPD4691	Approved
0.7292	Intermediate Similarity	NPD5207	Approved
0.7292	Intermediate Similarity	NPD5692	Phase 3
0.729	Intermediate Similarity	NPD8297	Approved
0.729	Intermediate Similarity	NPD6882	Approved
0.7263	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6903	Approved
0.7234	Intermediate Similarity	NPD6098	Approved
0.7228	Intermediate Similarity	NPD6404	Discontinued
0.7222	Intermediate Similarity	NPD4632	Approved
0.7216	Intermediate Similarity	NPD5694	Approved
0.7216	Intermediate Similarity	NPD6050	Approved
0.7212	Intermediate Similarity	NPD6008	Approved
0.7204	Intermediate Similarity	NPD3668	Phase 3
0.7196	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4754	Approved
0.7176	Intermediate Similarity	NPD4137	Phase 3
0.7128	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4747	Approved
0.7091	Intermediate Similarity	NPD6274	Approved
0.7087	Intermediate Similarity	NPD5091	Approved
0.7075	Intermediate Similarity	NPD5128	Approved
0.7075	Intermediate Similarity	NPD4729	Approved
0.7075	Intermediate Similarity	NPD4730	Approved
0.7053	Intermediate Similarity	NPD5279	Phase 3
0.7048	Intermediate Similarity	NPD4768	Approved
0.7048	Intermediate Similarity	NPD4767	Approved
0.7045	Intermediate Similarity	NPD4058	Approved
0.7041	Intermediate Similarity	NPD8034	Phase 2
0.7041	Intermediate Similarity	NPD8035	Phase 2
0.7027	Intermediate Similarity	NPD6317	Approved
0.7027	Intermediate Similarity	NPD6009	Approved
0.7009	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6313	Approved
0.6964	Remote Similarity	NPD6314	Approved
0.6964	Remote Similarity	NPD6335	Approved
0.6947	Remote Similarity	NPD1696	Phase 3
0.6944	Remote Similarity	NPD5169	Approved
0.6944	Remote Similarity	NPD5250	Approved
0.6944	Remote Similarity	NPD5251	Approved
0.6944	Remote Similarity	NPD5249	Phase 3
0.6944	Remote Similarity	NPD4634	Approved
0.6944	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5247	Approved
0.6944	Remote Similarity	NPD5135	Approved
0.6944	Remote Similarity	NPD5248	Approved
0.6939	Remote Similarity	NPD4096	Approved
0.6937	Remote Similarity	NPD6868	Approved
0.6931	Remote Similarity	NPD7732	Phase 3
0.693	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7632	Discontinued
0.6916	Remote Similarity	NPD5168	Approved
0.6915	Remote Similarity	NPD4788	Approved
0.6903	Remote Similarity	NPD7100	Approved
0.6903	Remote Similarity	NPD7101	Approved
0.6882	Remote Similarity	NPD4139	Approved
0.6882	Remote Similarity	NPD4692	Approved
0.6881	Remote Similarity	NPD5215	Approved
0.6881	Remote Similarity	NPD5216	Approved
0.6881	Remote Similarity	NPD5217	Approved
0.6881	Remote Similarity	NPD5127	Approved
0.6857	Remote Similarity	NPD6052	Approved
0.6842	Remote Similarity	NPD6319	Approved
0.6832	Remote Similarity	NPD5654	Approved
0.6824	Remote Similarity	NPD7331	Phase 2
0.6822	Remote Similarity	NPD6614	Approved
0.6822	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5133	Approved
0.6783	Remote Similarity	NPD5983	Phase 2
0.6774	Remote Similarity	NPD7525	Registered
0.6771	Remote Similarity	NPD5363	Approved
0.6768	Remote Similarity	NPD5785	Approved
0.6759	Remote Similarity	NPD6686	Approved
0.6739	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4518	Approved
0.6706	Remote Similarity	NPD7341	Phase 2
0.67	Remote Similarity	NPD6411	Approved
0.6699	Remote Similarity	NPD5959	Approved
0.6696	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7645	Phase 2
0.6638	Remote Similarity	NPD6908	Approved
0.6638	Remote Similarity	NPD6909	Approved
0.6634	Remote Similarity	NPD5779	Approved
0.6634	Remote Similarity	NPD5778	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