NPASS Compound

Structure

CID163963 OpenBabel06191715532D 28 31 0 0 1 0 0 0 0 0999 V2000 -2.0922 -1.0363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8979 -0.1851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7235 0.5681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0096 1.7562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5475 1.2340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6887 1.4302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5257 2.6426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2886 2.2022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5257 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1583 1.3213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5475 -0.3533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4630 0.5681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9299 0.4404 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.8809 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5257 0.8809 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7629 2.2022 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7629 -0.4404 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6886 -0.5493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8901 0.5479 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2886 1.3213 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7629 1.3213 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 4.8979 1.3213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0096 2.6371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7629 -1.3102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4942 -1.4010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7920 0.9774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5932 0.5681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 12 1 0 0 0 0 5 6 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 20 1 0 0 0 0 9 15 1 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 10 28 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 23 2 0 0 0 0 12 28 1 0 0 0 0 13 5 1 6 0 0 0 13 19 1 0 0 0 0 14 21 1 1 0 0 0 14 22 1 0 0 0 0 15 20 1 1 0 0 0 15 21 1 0 0 0 0 16 21 1 1 0 0 0 16 24 1 0 0 0 0 17 22 1 1 0 0 0 17 25 1 0 0 0 0 18 26 2 0 0 0 0 19 22 1 1 0 0 0 19 27 1 0 0 0 0 20 3 1 1 0 0 0 21 4 1 1 0 0 0 22 18 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.22
Volume:	399.674
LogP:	0.943
LogD:	0.855
LogS:	-3.711
# Rotatable Bonds:	3
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.487
Synthetic Accessibility Score:	6.148
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.98
MDCK Permeability:	9.094111192098353e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.741
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.704

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.292
Plasma Protein Binding (PPB):	29.191091537475586%
Volume Distribution (VD):	0.518
Pgp-substrate:	67.61577606201172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.153
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.621
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.06
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	2.337
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.292
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.054
AMES Toxicity:	0.24
Rat Oral Acute Toxicity:	0.953
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.546
Carcinogencity:	0.03
Eye Corrosion:	0.005
Eye Irritation:	0.035
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC163963

Natural Product ID:	NPC163963
*Common Name:**	SOISFJAFHWJMRU-AWQMTSQZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SOISFJAFHWJMRU-AWQMTSQZSA-N
Standard InCHI:	InChI=1S/C22H32O6/c1-11-13-5-6-14-21(4)15(9-17(25)22(14,18(11)26)19(13)27)20(3,8-7-16(21)24)10-28-12(2)23/h13-17,19,24-25,27H,1,5-10H2,2-4H3/t13-,14-,15+,16-,17+,19+,20+,21-,22-/m0/s1
SMILES:	C=C1[C@@H]2CC[C@H]3[C@@]4(C)[C@H](C[C@H]([C@@]3(C1=O)[C@@H]2O)O)[C@](C)(CC[C@@H]4O)COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472435
PubChem CID:	44575548
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO1238	Gentiana brachyphylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)94333-4]
NPO17628	Rabdosia excisa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043413]
NPO15395	Euphorbia portlandica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792416]
NPO3902	Aglaia edulis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190457]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	Heartwood	India	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[21784631]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15395	Euphorbia portlandica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17628	Rabdosia excisa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1238	Gentiana brachyphylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8694	Picrasma crenata	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18360	Isodon weisiensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17628	Rabdosia excisa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8694	Picrasma crenata	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3902	Aglaia edulis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15395	Euphorbia portlandica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1238	Gentiana brachyphylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1238	Gentiana brachyphylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18360	Isodon weisiensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8694	Picrasma crenata	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6120	Attalea funifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7594	Muricea californica	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17628	Rabdosia excisa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5138	Colebrookea oppositifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3038	Veronica linariifolia	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3902	Aglaia edulis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4558	Polysaccum crassipes	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11368	Leontodon tuberosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8191	Lecanora epanora	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO265	Helminthosporium zizaniae	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15395	Euphorbia portlandica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1531	Chlorella sorokiniana	Species	Chlorellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4800	Cyrtocymura cincta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1238	Gentiana brachyphylla	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21411	Santolina magonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO688	Scorzonera cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.72	ug.mL-1	PMID[521638]

☑ 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 NPC163963 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	228
0.1-0.2	1643
0.2-0.3	5379
0.3-0.4	9304
0.4-0.5	11366
0.5-0.6	6026
0.6-0.7	5562
0.7-0.8	2678
0.8-0.85	298
0.85-0.9	97
0.9-0.95	87
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC52899
1.0	High Similarity	NPC289148
0.9894	High Similarity	NPC88203
0.9894	High Similarity	NPC304832
0.9894	High Similarity	NPC286519
0.9894	High Similarity	NPC214946
0.9894	High Similarity	NPC148628
0.9894	High Similarity	NPC76866
0.9894	High Similarity	NPC246736
0.9892	High Similarity	NPC287676
0.9789	High Similarity	NPC87927
0.9785	High Similarity	NPC78427
0.9785	High Similarity	NPC16911
0.9688	High Similarity	NPC98603
0.9583	High Similarity	NPC216114
0.9579	High Similarity	NPC46848
0.9574	High Similarity	NPC471038
0.957	High Similarity	NPC329910
0.957	High Similarity	NPC13949
0.9485	High Similarity	NPC84928
0.9479	High Similarity	NPC275990
0.9462	High Similarity	NPC470232
0.9462	High Similarity	NPC210214
0.9462	High Similarity	NPC470229
0.9394	High Similarity	NPC218123
0.9394	High Similarity	NPC231278
0.9394	High Similarity	NPC112895
0.9375	High Similarity	NPC471790
0.9368	High Similarity	NPC162459
0.9368	High Similarity	NPC20479
0.9368	High Similarity	NPC28864
0.9368	High Similarity	NPC38471
0.9368	High Similarity	NPC98837
0.9368	High Similarity	NPC474793
0.9368	High Similarity	NPC38296
0.9362	High Similarity	NPC29410
0.9362	High Similarity	NPC200054
0.9355	High Similarity	NPC470385
0.9355	High Similarity	NPC470386
0.9355	High Similarity	NPC47853
0.9355	High Similarity	NPC475118
0.9286	High Similarity	NPC474558
0.9286	High Similarity	NPC202793
0.9278	High Similarity	NPC309388
0.9278	High Similarity	NPC475803
0.9271	High Similarity	NPC293866
0.9255	High Similarity	NPC98639
0.9247	High Similarity	NPC144739
0.9247	High Similarity	NPC294263
0.9247	High Similarity	NPC181594
0.92	High Similarity	NPC273155
0.9192	High Similarity	NPC138908
0.9192	High Similarity	NPC4115
0.9192	High Similarity	NPC37600
0.9192	High Similarity	NPC200957
0.9184	High Similarity	NPC139347
0.9184	High Similarity	NPC277074
0.9184	High Similarity	NPC209298
0.9184	High Similarity	NPC470310
0.9184	High Similarity	NPC122811
0.9175	High Similarity	NPC236585
0.9167	High Similarity	NPC89099
0.9158	High Similarity	NPC470387
0.9149	High Similarity	NPC261333
0.9149	High Similarity	NPC101233
0.9149	High Similarity	NPC111524
0.9149	High Similarity	NPC153775
0.9149	High Similarity	NPC104371
0.9149	High Similarity	NPC91772
0.9149	High Similarity	NPC292374
0.9149	High Similarity	NPC129004
0.9149	High Similarity	NPC215271
0.9149	High Similarity	NPC29247
0.9149	High Similarity	NPC289539
0.914	High Similarity	NPC198242
0.914	High Similarity	NPC476168
0.914	High Similarity	NPC211403
0.914	High Similarity	NPC470230
0.914	High Similarity	NPC299185
0.914	High Similarity	NPC250753
0.9118	High Similarity	NPC329953
0.91	High Similarity	NPC166993
0.91	High Similarity	NPC201908
0.91	High Similarity	NPC176949
0.9091	High Similarity	NPC96268
0.9091	High Similarity	NPC13149
0.9072	High Similarity	NPC470388
0.9062	High Similarity	NPC10864
0.9053	High Similarity	NPC84018
0.9053	High Similarity	NPC138245
0.9053	High Similarity	NPC231060
0.9032	High Similarity	NPC149761
0.9032	High Similarity	NPC80401
0.9032	High Similarity	NPC261994
0.9032	High Similarity	NPC470378
0.9032	High Similarity	NPC180849
0.902	High Similarity	NPC471093
0.901	High Similarity	NPC211224
0.9	High Similarity	NPC295366
0.9	High Similarity	NPC12823
0.899	High Similarity	NPC159442
0.899	High Similarity	NPC96217
0.898	High Similarity	NPC252614
0.898	High Similarity	NPC148279
0.898	High Similarity	NPC253886
0.898	High Similarity	NPC121218
0.8958	High Similarity	NPC135548
0.8958	High Similarity	NPC264979
0.8958	High Similarity	NPC140242
0.8947	High Similarity	NPC191094
0.8947	High Similarity	NPC302008
0.8942	High Similarity	NPC471252
0.8932	High Similarity	NPC470281
0.8932	High Similarity	NPC29505
0.8925	High Similarity	NPC471043
0.89	High Similarity	NPC301787
0.8889	High Similarity	NPC170615
0.8878	High Similarity	NPC94906
0.8878	High Similarity	NPC267921
0.8846	High Similarity	NPC474927
0.8842	High Similarity	NPC59350
0.8842	High Similarity	NPC59170
0.8824	High Similarity	NPC63841
0.8824	High Similarity	NPC55973
0.8824	High Similarity	NPC469733
0.8824	High Similarity	NPC469729
0.8812	High Similarity	NPC265127
0.8812	High Similarity	NPC222833
0.88	High Similarity	NPC469985
0.8788	High Similarity	NPC75941
0.8788	High Similarity	NPC295276
0.8788	High Similarity	NPC71706
0.8788	High Similarity	NPC14634
0.8776	High Similarity	NPC26270
0.8776	High Similarity	NPC472028
0.8763	High Similarity	NPC234564
0.8763	High Similarity	NPC104568
0.875	High Similarity	NPC213320
0.875	High Similarity	NPC94650
0.875	High Similarity	NPC64006
0.8738	High Similarity	NPC102741
0.8738	High Similarity	NPC469744
0.8725	High Similarity	NPC88833
0.8725	High Similarity	NPC96333
0.8725	High Similarity	NPC469746
0.8725	High Similarity	NPC67745
0.8725	High Similarity	NPC471461
0.8725	High Similarity	NPC186054
0.8713	High Similarity	NPC47281
0.871	High Similarity	NPC153604
0.871	High Similarity	NPC165895
0.871	High Similarity	NPC259009
0.871	High Similarity	NPC174619
0.87	High Similarity	NPC124544
0.8692	High Similarity	NPC473304
0.8687	High Similarity	NPC127408
0.8687	High Similarity	NPC37047
0.8687	High Similarity	NPC55503
0.8687	High Similarity	NPC180733
0.8687	High Similarity	NPC41971
0.8687	High Similarity	NPC108371
0.8687	High Similarity	NPC291785
0.8687	High Similarity	NPC156324
0.8673	High Similarity	NPC96839
0.8673	High Similarity	NPC253586
0.8667	High Similarity	NPC473352
0.8667	High Similarity	NPC471245
0.8667	High Similarity	NPC473397
0.866	High Similarity	NPC288906
0.866	High Similarity	NPC29112
0.866	High Similarity	NPC263135
0.8654	High Similarity	NPC137104
0.8654	High Similarity	NPC320383
0.8654	High Similarity	NPC474786
0.8654	High Similarity	NPC473324
0.8646	High Similarity	NPC224060
0.8646	High Similarity	NPC244356
0.8641	High Similarity	NPC473410
0.8641	High Similarity	NPC189663
0.8641	High Similarity	NPC471094
0.8641	High Similarity	NPC232133
0.8641	High Similarity	NPC469984
0.8641	High Similarity	NPC89860
0.8627	High Similarity	NPC28791
0.8627	High Similarity	NPC50535
0.8602	High Similarity	NPC471042
0.86	High Similarity	NPC39683
0.8598	High Similarity	NPC88945
0.8585	High Similarity	NPC471248
0.8585	High Similarity	NPC132668
0.8571	High Similarity	NPC219353
0.8571	High Similarity	NPC122339
0.8558	High Similarity	NPC252679
0.8558	High Similarity	NPC274827
0.8558	High Similarity	NPC118721
0.8558	High Similarity	NPC469983
0.8558	High Similarity	NPC131903
0.8544	High Similarity	NPC61071
0.8544	High Similarity	NPC86852
0.8544	High Similarity	NPC471474

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 NPC163963 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	2027
0.2-0.3	3926
0.3-0.4	1908
0.4-0.5	583
0.5-0.6	207
0.6-0.7	157
0.7-0.8	124
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.798	Intermediate Similarity	NPD8035	Phase 2
0.798	Intermediate Similarity	NPD8034	Phase 2
0.7944	Intermediate Similarity	NPD6881	Approved
0.7944	Intermediate Similarity	NPD6899	Approved
0.7925	Intermediate Similarity	NPD5739	Approved
0.7925	Intermediate Similarity	NPD7128	Approved
0.7925	Intermediate Similarity	NPD6675	Approved
0.7925	Intermediate Similarity	NPD6402	Approved
0.7917	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.789	Intermediate Similarity	NPD6650	Approved
0.789	Intermediate Similarity	NPD6649	Approved
0.787	Intermediate Similarity	NPD6373	Approved
0.787	Intermediate Similarity	NPD6372	Approved
0.785	Intermediate Similarity	NPD5697	Approved
0.7807	Intermediate Similarity	NPD6319	Approved
0.7798	Intermediate Similarity	NPD7290	Approved
0.7798	Intermediate Similarity	NPD6883	Approved
0.7798	Intermediate Similarity	NPD7102	Approved
0.7778	Intermediate Similarity	NPD7320	Approved
0.7757	Intermediate Similarity	NPD6008	Approved
0.7727	Intermediate Similarity	NPD6869	Approved
0.7727	Intermediate Similarity	NPD8130	Phase 1
0.7727	Intermediate Similarity	NPD6847	Approved
0.7727	Intermediate Similarity	NPD6617	Approved
0.7723	Intermediate Similarity	NPD6399	Phase 3
0.7706	Intermediate Similarity	NPD6012	Approved
0.7706	Intermediate Similarity	NPD6013	Approved
0.7706	Intermediate Similarity	NPD6014	Approved
0.7692	Intermediate Similarity	NPD7638	Approved
0.7692	Intermediate Similarity	NPD7492	Approved
0.7685	Intermediate Similarity	NPD5701	Approved
0.7658	Intermediate Similarity	NPD8297	Approved
0.7658	Intermediate Similarity	NPD6882	Approved
0.7652	Intermediate Similarity	NPD6054	Approved
0.7647	Intermediate Similarity	NPD7736	Approved
0.7627	Intermediate Similarity	NPD6616	Approved
0.7624	Intermediate Similarity	NPD6079	Approved
0.7619	Intermediate Similarity	NPD7640	Approved
0.7619	Intermediate Similarity	NPD7639	Approved
0.7615	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD6011	Approved
0.76	Intermediate Similarity	NPD5328	Approved
0.7589	Intermediate Similarity	NPD4632	Approved
0.7563	Intermediate Similarity	NPD7078	Approved
0.7553	Intermediate Similarity	NPD6118	Approved
0.7553	Intermediate Similarity	NPD6114	Approved
0.7553	Intermediate Similarity	NPD6115	Approved
0.7553	Intermediate Similarity	NPD6697	Approved
0.7544	Intermediate Similarity	NPD7115	Discovery
0.7526	Intermediate Similarity	NPD4788	Approved
0.7521	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.7477	Intermediate Similarity	NPD4634	Approved
0.7476	Intermediate Similarity	NPD7748	Approved
0.7453	Intermediate Similarity	NPD5285	Approved
0.7453	Intermediate Similarity	NPD5286	Approved
0.7453	Intermediate Similarity	NPD4696	Approved
0.7451	Intermediate Similarity	NPD7515	Phase 2
0.7436	Intermediate Similarity	NPD6015	Approved
0.7436	Intermediate Similarity	NPD6016	Approved
0.7429	Intermediate Similarity	NPD6083	Phase 2
0.7429	Intermediate Similarity	NPD4755	Approved
0.7429	Intermediate Similarity	NPD6084	Phase 2
0.7429	Intermediate Similarity	NPD7902	Approved
0.7417	Intermediate Similarity	NPD8293	Discontinued
0.7411	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6009	Approved
0.7373	Intermediate Similarity	NPD5988	Approved
0.734	Intermediate Similarity	NPD6117	Approved
0.7333	Intermediate Similarity	NPD5221	Approved
0.7333	Intermediate Similarity	NPD4697	Phase 3
0.7333	Intermediate Similarity	NPD5222	Approved
0.7333	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5226	Approved
0.7315	Intermediate Similarity	NPD5225	Approved
0.7315	Intermediate Similarity	NPD4633	Approved
0.7315	Intermediate Similarity	NPD5224	Approved
0.7315	Intermediate Similarity	NPD5211	Phase 2
0.7311	Intermediate Similarity	NPD7604	Phase 2
0.7311	Intermediate Similarity	NPD8328	Phase 3
0.7304	Intermediate Similarity	NPD6274	Approved
0.73	Intermediate Similarity	NPD3618	Phase 1
0.7295	Intermediate Similarity	NPD7319	Approved
0.729	Intermediate Similarity	NPD4700	Approved
0.7288	Intermediate Similarity	NPD5983	Phase 2
0.7282	Intermediate Similarity	NPD6411	Approved
0.7273	Intermediate Similarity	NPD4786	Approved
0.7265	Intermediate Similarity	NPD7101	Approved
0.7265	Intermediate Similarity	NPD7100	Approved
0.7264	Intermediate Similarity	NPD5173	Approved
0.7263	Intermediate Similarity	NPD6116	Phase 1
0.7248	Intermediate Similarity	NPD5175	Approved
0.7248	Intermediate Similarity	NPD5174	Approved
0.7241	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3703	Phase 2
0.7222	Intermediate Similarity	NPD5223	Approved
0.7196	Intermediate Similarity	NPD4225	Approved
0.7196	Intermediate Similarity	NPD5696	Approved
0.719	Intermediate Similarity	NPD6336	Discontinued
0.719	Intermediate Similarity	NPD7507	Approved
0.7182	Intermediate Similarity	NPD5141	Approved
0.7179	Intermediate Similarity	NPD6335	Approved
0.7157	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7632	Discontinued
0.7155	Intermediate Similarity	NPD6868	Approved
0.7143	Intermediate Similarity	NPD7900	Approved
0.7143	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD8133	Approved
0.7129	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7521	Approved
0.7129	Intermediate Similarity	NPD7334	Approved
0.7129	Intermediate Similarity	NPD6684	Approved
0.7129	Intermediate Similarity	NPD7146	Approved
0.7129	Intermediate Similarity	NPD6409	Approved
0.7129	Intermediate Similarity	NPD5330	Approved
0.7128	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6317	Approved
0.7087	Intermediate Similarity	NPD6101	Approved
0.7087	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5695	Phase 3
0.7075	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3667	Approved
0.7054	Intermediate Similarity	NPD6412	Phase 2
0.7048	Intermediate Similarity	NPD4202	Approved
0.7048	Intermediate Similarity	NPD5778	Approved
0.7048	Intermediate Similarity	NPD5779	Approved
0.7034	Intermediate Similarity	NPD6313	Approved
0.7034	Intermediate Similarity	NPD6314	Approved
0.7	Intermediate Similarity	NPD6908	Approved
0.7	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6909	Approved
0.6991	Remote Similarity	NPD4730	Approved
0.6991	Remote Similarity	NPD4729	Approved
0.6991	Remote Similarity	NPD5128	Approved
0.699	Remote Similarity	NPD5737	Approved
0.699	Remote Similarity	NPD6903	Approved
0.699	Remote Similarity	NPD6672	Approved
0.6964	Remote Similarity	NPD4768	Approved
0.6964	Remote Similarity	NPD4767	Approved
0.6952	Remote Similarity	NPD7637	Suspended
0.6937	Remote Similarity	NPD4754	Approved
0.6935	Remote Similarity	NPD6033	Approved
0.6931	Remote Similarity	NPD3133	Approved
0.6931	Remote Similarity	NPD3666	Approved
0.6931	Remote Similarity	NPD3665	Phase 1
0.693	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4753	Phase 2
0.6916	Remote Similarity	NPD4629	Approved
0.6916	Remote Similarity	NPD5210	Approved
0.6915	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6053	Discontinued
0.6893	Remote Similarity	NPD3573	Approved
0.687	Remote Similarity	NPD5250	Approved
0.687	Remote Similarity	NPD5251	Approved
0.687	Remote Similarity	NPD5248	Approved
0.687	Remote Similarity	NPD5249	Phase 3
0.687	Remote Similarity	NPD5247	Approved
0.686	Remote Similarity	NPD6921	Approved
0.6842	Remote Similarity	NPD6686	Approved
0.681	Remote Similarity	NPD5217	Approved
0.681	Remote Similarity	NPD5215	Approved
0.681	Remote Similarity	NPD5216	Approved
0.6783	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6080	Approved
0.6762	Remote Similarity	NPD6673	Approved
0.6762	Remote Similarity	NPD6904	Approved
0.6759	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5777	Approved
0.6726	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5135	Approved
0.6724	Remote Similarity	NPD6371	Approved
0.6724	Remote Similarity	NPD5169	Approved
0.6718	Remote Similarity	NPD6334	Approved
0.6718	Remote Similarity	NPD6333	Approved
0.6702	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD3702	Approved
0.67	Remote Similarity	NPD7525	Registered
0.6698	Remote Similarity	NPD5785	Approved
0.6696	Remote Similarity	NPD5168	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6636	Remote Similarity	NPD5284	Approved
0.6636	Remote Similarity	NPD5281	Approved
0.6635	Remote Similarity	NPD6098	Approved
0.6635	Remote Similarity	NPD5786	Approved
0.6634	Remote Similarity	NPD5369	Approved
0.6632	Remote Similarity	NPD4245	Approved
0.6632	Remote Similarity	NPD4244	Approved
0.6612	Remote Similarity	NPD7328	Approved
0.6612	Remote Similarity	NPD7327	Approved
0.6607	Remote Similarity	NPD1700	Approved
0.6602	Remote Similarity	NPD3668	Phase 3
0.6585	Remote Similarity	NPD8033	Approved
0.6569	Remote Similarity	NPD4221	Approved
0.6569	Remote Similarity	NPD4223	Phase 3
0.6569	Remote Similarity	NPD6435	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